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TiHKAL#6 DMT
5006
Variant: N N+ α R1 R2 R4 R5 R6 R7 skeleton isomers all
Analogues: 92 1 1 2 1 9 15 8 6 13 10 158

IUPAC: 2-(1H-Indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: DMULVCHRPCFFGV-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3

PubChem CID: 6089; ChemSpider: 5864; Drugs Forum: DMT; Erowid: DMT; Wikipedia: Dimethyltryptamine

See also TiHKAL: #2 DBT
#3 DET
#5 α,O-DMS
#7 2,α-DMT
#8 α,N-DMT
#9 DPT
#13 Harmaline
#14 Harmine
#16 4-HO-DET
#21 4-HO-MET
#27 MBT
#30 4,5-MDO-DMT
#31 5,6-MDO-DMT
#34 2-Me-DMT
#35 Melatonin
#38 5-MeO-DMT
#39 4-MeO-MIPT
#41 5,6-MeO-MIPT
#42 5-MeO-NMT
#43 5-MeO-pyr-T
#44 6-MeO-THH
#47 MIPT
#48 α-MT
#50 NMT
#52 pyr-T
#53 T
#54 Tetrahydroharmine
#55 α,N,O-TMS
#57 DALT

See also Transcripts: 1.137, 3.327

See also Pharmacology notes I: p. 137, DMT
See also Chemistry notes VIII: p. 66, DMT: Synthesis
p. 67, DMT: GC-MS
p. 68, DMT: GC-MS
p. 70, DMT: Synthesis
p. 71, DMT: GC-MS
p. 132, DMT: Synthesis

Brandt, SD; Moore, SA; Freeman, S; Kanu, AB. Characterization of the synthesis of N,N-dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry. Drug Test. Anal., 1 Jul 2010, 2 (7), 330–338. 192 kB. doi:10.1002/dta.142

Fenderson5555. DMT from tryptophan? 23 Mar 2011. Wanted! Please contact me if you find this video.

Fenderson5555. Mechanisms in DMT synthesis. 3 Jan 2011. 2609 kB.

McIlhenny, EH; Pipkin, KE; Standish, LJ; Wechkin, HA; Strassman, R; Barker, SA. Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry. J. Chromatogr. A, 18 Dec 2009, 1216 (51), 8960–8968. 450 kB. doi:10.1016/j.chroma.2009.10.088

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

Szara, S; Axelrod, J. Hydroxylation and N-demethylation of N,N-dimethyltryptamine. Experientia, 1 Jun 1959, 15 (6), 216–217. 304 kB. doi:10.1007/BF02158111

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Strassman, RJ. Human psychopharmacology of N,N,-dimethyltryptamine. Behav. Brain Res., 15 Dec 1995, 73 (1–2), 121–124. 396 kB. doi:10.1016/0166-4328(96)00081-2

Su, T; Hayashi, T; Vaupel, DB. When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor. Sci. Signal., 10 Mar 2009, 2 (61), 1–4. 392 kB. doi:10.1126/scisignal.261pe12

Martins, CPB; Freeman, S; Alder, JF; Brandt, SD. Characterisation of a proposed internet synthesis of N,N-dimethyltryptamine using liquid chromatography/electrospray ionisation tandem mass spectrometry. J. Chromatogr. A, 14 Aug 2009, 1216 (33), 6119–6123. 315 kB. doi:10.1016/j.chroma.2009.06.060

Pires, APS; Oliveira, CDR; Moura, S; Dörr, FA; Silva, WAE; Yonamine, M. Gas chromatographic analysis of dimethyltryptamine and β-carboline alkaloids in ayahuasca, an Amazonian psychoactive plant beverage. Phytochem. Anal., 1 Mar 2009, 20 (2), 149–153. 131 kB. doi:10.1002/pca.1110

Brandt, SD; Martins, CPB; Freeman, S; Dempster, N; Riby, PG; Gartz, J; Alder, JF. Halogenated solvent interactions with N,N-dimethyltryptamine: Formation of quaternary ammonium salts and their artificially induced rearrangements during analysis. Forensic Sci. Int., 4 Jul 2008, 178 (2–3), 162–170. 785 kB. doi:10.1016/j.forsciint.2008.03.013

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Jacob, MS; Presti, DE. Endogenous psychoactive tryptamines reconsidered: an anxiolytic role for dimethyltryptamine. Med. Hypotheses, 2005, 64 (5), 930–937. 162 kB. doi:10.1016/j.mehy.2004.11.005

Gaujac, A; Ford, JL; Dempster, NM; Andrade, JB; Brandt, SD. Investigations into the polymorphic properties of N,N-dimethyltryptamine by X-ray diffraction and differential scanning calorimetry. Microchem. J., 1 Sep 2013, 110, 146–157. 1166 kB. doi:10.1016/j.microc.2013.03.009

Blackledge, RD; Taylor, CM. Psychotria viridis—A botanical source of dimethyltryptamine (DMT). Microgram J., 1 Jan 2003, 1 (1–2), 18–22. 429 kB.

Fasanello, JA; Placke, AD. The isolation, identification, and quantitation of dimethyltryptamine (DMT) in Mimosa Hostilis. Microgram J., 1 Jan 2007, 5 (1–4), 41–52. 168 kB.

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed. Chromatogr., 1 Mar 2012, 26 (3), 301–313. 557 kB. doi:10.1002/bmc.1657

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine. Biomed. Chromatogr., 1 Sep 2011, 25 (9), 970–984. 1030 kB. doi:10.1002/bmc.1551

Gambelunghe, C; Aroni, K; Rossi, R; Moretti, L; Bacci, M. Identification of N,N-dimethyltryptamine and β-carbolines in psychotropic ayahuasca beverage. Biomed. Chromatogr., 1 Oct 2008, 22 (10) 1056–1059. 140 kB. doi:10.1002/bmc.1023

Szára, S. The comparison of the psychotic effect of tryptamine derivatives with the effects of mescaline and LSD-25 in self-experiments. In Psychotropic Drugs [proceedings]; Garattini, S; Ghetti, V, Eds., Elsevier, 1957; pp 460–467. 480 kB.

Moura, S; Carvalho, FG; Oliveira, CDR; Pinto, E; Yonamine, M. qNMR: An applicable method for the determination of dimethyltryptamine in ayahuasca, a psychoactive plant preparation. Phytochem. Lett., 11 Jun 2010, 3 (2), 79–83. 227 kB. doi:10.1016/j.phytol.2009.12.004

Gaujac, A; Martinez, ST; Gomes, AA; Andrade, SJ; Pinto, AC; David, JM; Navickiene, S; Andrade, JB. Application of analytical methods for the structural characterization and purity assessment of N,N-dimethyltryptamine, a potent psychedelic agent isolated from Mimosa tenuiflora inner barks. Microchem. J., Jul 2013. 685 kB. doi:10.1016/j.microc.2012.03.033

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Barker, SA; McIlhenny, EH; Strassman, R. A critical review of reports of endogenous psychedelic N,N-dimethyltryptamines in humans: 1955–2010. Drug Test. Anal., 2012. 270 kB. doi:10.1002/dta.422

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3077 kB. doi:10.1007/BF02818560

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Cozzi, NV; Shulgin, AT; Daley, PF; Gopalakrishnan, A; Anderson, LL; Feih, JT; Ruoho, AE. Psychoactive N,N-dialkyltryptamines modulate serotonin transport by at least two mechanisms. Soc. Neurosci. Abs., 1 Jan 2008, 536.17. 52 kB.

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture: rational exploration of the underground, 5 Dec 2011.

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Brandt, SD; Tearavarich, R; Dempster, N; Cozzi, NV; Daley, PF. Synthesis and characterization of 5-methoxy-2-methyl-N,N-dialkylated tryptamines. Drug Test. Anal., 1 Jan 2012, 4 (1), 24–32. 506 kB. doi:10.1002/dta.398

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Cozzi, NV; Gopalakrishnan, A; Anderson, LL; Feih, JT; Shulgin, AT; Daley, PF; Ruoho, AE. Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter. J. Neural. Transm., 1 Dec 2009, 116 (12), 1591–1599. 420 kB. doi:10.1007/s00702-009-0308-8

Shulgin, AT. DMT and tryptophan. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 19 Sep 2002.

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916):,934–937. 529 kB. doi:10.1126/science.1166127

Shulgin, AT. Profiles of psychedelic drugs. 1. DMT; 2. TMA-2. J. Psychedelic Drugs, 1 Jan 1976, 8 (2), 167–169. 2097 kB. doi:10.1080/02791072.1976.10471846

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Kline, TB; Benington, F; Morin, RD; Beaton, JM; Glennon, RA; Domelsmith, LN; Houk, KN; Rozeboom, MD. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives. J. Med. Chem., 1 Jan 1982, 25 (11), 1381–1383. 378 kB. doi:10.1021/jm00353a021

Böszörményi, Z; Szára, S. Dimethyltryptamine experiments with psychotics. Br. J. Psychiatry, 1 Apr 1958, 104 (435), 445–453. 1274 kB. doi:10.1192/bjp.104.435.445

Ciprian-Ollivier, J; Cetkovich-Bakmas, MG. Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr. Res., 19 Dec 1997, 28 (2–3), 257–265. 722 kB. doi:10.1039/S0920-9964(97)00116-3

Szara, S. Dimethyltryptamin: Its metabolism in man; the relation to its psychotic effect to the serotonin metabolism. Experientia, 1 Jan 1956, 12 (11), 441–442. 333 kB. doi:10.1007/BF02157378

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1056 kB. doi:10.1016/0028-3908(62)90015-1

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

92 N analogues:
5002
Analogue 1: Substituting Dibutyl for Dimethyl at N

DBT
Tryptamine, N,N-dibutyl
Indole, 3-[2-(dibutylamino)ethyl]
N,N-Dibutyltryptamine
3-[2-(Dibutylamino)ethyl]indole

IUPAC: N-Butyl-N-[2-(1H-indol-3-yl)ethyl]butan-1-amine

Formula: C18H28N2 Molecular weight: 272.42832 g/mol InChI Key: LZLJUZWFWYEQLY-UHFFFAOYSA-N

InChI=1S/C18H28N2/c1-3-5-12-20(13-6-4-2)14-11-16-15-19-18-10-8-7-9-17(16)18/h7-10,15,19H,3-6,11-14H2,1-2H3

PubChem CID: 27848; ChemSpider: 25911; Wikipedia: Dibutyltryptamine

See also TiHKAL: #27 MBT #49 NET

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1056 kB. doi:10.1016/0028-3908(62)90015-1

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

5003
Analogue 2: Substituting Diethyl for Dimethyl at N

DET
T-9
Tryptamine, N,N-diethyl
Indole, 3-[2-(diethylamino)ethyl]
N,N-Diethyltryptamine
3-[2-(Diethylamino)ethyl]indole

IUPAC: N,N-Diethyl-2-(1H-indol-3-yl)ethan-1-amine

Formula: C14H20N2 Molecular weight: 216.322 g/mol InChI Key: LSSUMOWDTKZHHT-UHFFFAOYSA-N

InChI=1S/C14H20N2/c1-3-16(4-2)10-9-12-11-15-14-8-6-5-7-13(12)14/h5-8,11,15H,3-4,9-10H2,1-2H3

PubChem CID: 6090; ChemSpider: 5865; Erowid: DET; Wikipedia: Diethyltryptamine

See also PiHKAL: #97 4-MA  
See also TiHKAL: #2 DBT
#5 α,O-DMS
#6 DMT
#7 2,α-DMT
#8 α,N-DMT
#9 DPT
#10 EIPT
#16 4-HO-DET
#27 MBT
#30 4,5-MDO-DMT
#33 2-Me-DET
#38 5-MeO-DMT
#52 pyr-T
#57 DALT
See also Chemistry notes VIII: p. 86, DET: Synthesis
p. 96, DET: GC-MS
p. 97, DET: GC-MS

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Gartz, J. Biotransformation of tryptamine derivatives in mycelia cultures of Psilocybe. J. Basic. Microbiol., 1989, 29 (6), 347–352. 357 kB. doi:10.1002/jobm.3620290608

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

Szára, S. The comparison of the psychotic effect of tryptamine derivatives with the effects of mescaline and LSD-25 in self-experiments. In Psychotropic Drugs [proceedings]; Garattini, S; Ghetti, V, Eds., Elsevier, 1957; pp 460–467. 480 kB.

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed. Chromatogr., 1 Mar 2012, 26 (3), 301–313. 557 kB. doi:10.1002/bmc.1657

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Böszörményi, Z; Dér, P. Observations on the psychotogenic effect of N,N diethyltryptamine, a new tryptamine derivative. J. Mental Sci., 1 Jan 1959, 105 (438), 171–181. 1388 kB. doi:10.1192/bjp.105.438.171

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1056 kB. doi:10.1016/0028-3908(62)90015-1

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Faillace, LA; Vourlekis, A; Szara, S. Clinical evaluation of some hallucinogenic tryptamine derivatives. J. Nerv. Ment. Dis., 1 Jan 1967, 145 (4), 306–313. 635 kB.

Szara, S. DMT (N,N-dimethyltryptamine) and homologues: Clinical and pharmacological considerations. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 275–286. 1897 kB.

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

5004
Analogue 3: Substituting Diisopropyl for Dimethyl at N

DIPT
Tryptamine, N,N-diisopropyl
Indole, 3-[2-(diisopropylamino)ethyl]
N,N-Diisopropyltryptamine
3-[2-(Diisopropylamino)ethyl]indole

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine

Formula: C16H24N2 Molecular weight: 244.37516 g/mol InChI Key: ZRVAAGAZUWXRIP-UHFFFAOYSA-N

InChI=1S/C16H24N2/c1-12(2)18(13(3)4)10-9-14-11-17-16-8-6-5-7-15(14)16/h5-8,11-13,17H,9-10H2,1-4H3

PubChem CID: 26903; ChemSpider: 25060; Erowid: DIPT; Wikipedia: Diisopropyltryptamine

See also TiHKAL: #10 EIPT
#33 2-Me-DET
#37 5-MeO-DIPT
#47 MIPT

See also Transcripts: 1.177

See also Pharmacology notes I: p. 177, DIPT: Trials
See also Chemistry notes VIII: p. 87, DIPT: Synthesis
p. 89, DIPT: Synthesis
p. 99, DIPT: GC-MS
p. 100, DIPT: Synthesis
p. 210, DIPT: Synthesis
p. 211, DIPT: GC-MS

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

Shulgin, AT; Shulgin, LA; Jacob, P. A protocol for the evaluation of new psychoactive drugs. Meth. Find. Exp. Clin. Pharmacol., 1 May 1986, 8 (5), 313. 7938 kB.

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Shulgin, AT. DIPT: The distortion of music. High Frontiers/Reality Hackers, 1 Jan 1988, 6, Winter, 27. 54 kB.

Shulgin, AT; Carter, MF. N,N-diisopropyltryptamine (DIPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT). Two orally active tryptamine analogs with CNS activity. Commun. Psychopharmacol., 1 Jan 1981, 4 (5), 363–369. 1166 kB.

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Cozzi, NV; Shulgin, AT; Daley, PF; Gopalakrishnan, A; Anderson, LL; Feih, JT; Ruoho, AE. Psychoactive N,N-dialkyltryptamines modulate serotonin transport by at least two mechanisms. Soc. Neurosci. Abs., 1 Jan 2008, 536.17. 52 kB.

Cozzi, NV; Gopalakrishnan, A; Anderson, LL; Feih, JT; Shulgin, AT; Daley, PF; Ruoho, AE. Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter. J. Neural. Transm., 1 Dec 2009, 116 (12), 1591–1599. 420 kB. doi:10.1007/s00702-009-0308-8

Gatch, MB; Forster, MJ; Janowsky, A; Eshleman, AJ. Abuse liability profile of three substituted tryptamines. J. Pharmacol. Exp. Ther., 1 Jul 2011, 338 (1), 280–289. 1188 kB. doi:10.1124/jpet.111.179705

5009
Analogue 4: Substituting Dipropyl for Dimethyl at N

DPT
Tryptamine, N,N-dipropyl
Indole, 3-[2-(dipropylamino)ethyl]
N,N-Dipropyltryptamine
3-[2-(Dipropylamino)ethyl]indole

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-propylpropan-1-amine

Formula: C16H24N2 Molecular weight: 244.37516 g/mol InChI Key: BOOQTIHIKDDPRW-UHFFFAOYSA-N

InChI=1S/C16H24N2/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16/h5-8,13,17H,3-4,9-12H2,1-2H3

PubChem CID: 6091; ChemSpider: 5866; Erowid: DPT; Wikipedia: Dipropyltryptamine

See also TiHKAL: #2 DBT
#20 4-HO-DPT
#27 MBT
#49 NET

See also Transcripts: 4.462

See also Chemistry notes VIII: p. 63, DPT: GC-MS
p. 83, DPT: Synthesis
p. 84, DPT: GC-MS
p. 85, DPT: GC-MS

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Shulgin, AT. Abused substances. Tech. Rev., 1 Jan 2005, August, 80–81. 415 kB.

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1056 kB. doi:10.1016/0028-3908(62)90015-1

Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines. Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB.

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Cozzi, NV; Shulgin, AT; Daley, PF; Gopalakrishnan, A; Anderson, LL; Feih, JT; Ruoho, AE. Psychoactive N,N-dialkyltryptamines modulate serotonin transport by at least two mechanisms. Soc. Neurosci. Abs., 1 Jan 2008, 536.17. 52 kB.

Toad. DPT Primer. Erowid, 15 Nov 1998.

Cozzi, NV; Gopalakrishnan, A; Anderson, LL; Feih, JT; Shulgin, AT; Daley, PF; Ruoho, AE. Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter. J. Neural. Transm., 1 Dec 2009, 116 (12), 1591–1599. 420 kB. doi:10.1007/s00702-009-0308-8

Faillace, LA; Vourlekis, A; Szara, S. Clinical evaluation of some hallucinogenic tryptamine derivatives. J. Nerv. Ment. Dis., 1 Jan 1967, 145 (4), 306–313. 635 kB.

Szara, S. DMT (N,N-dimethyltryptamine) and homologues: Clinical and pharmacological considerations. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 275–286. 1897 kB.

5010
Analogue 5: Substituting Ethyl and Isopropyl for Dimethyl at N

EIPT
Tryptamine, N-ethyl-N-isopropyl
Indole, 3-[2-(ethylisopropylamino)ethyl]
N-Ethyl-N-isopropyltryptamine
3-[2-(Ethylisopropylamino)ethyl]indole

IUPAC: N-Ethyl-N-[2-(1H-indol-3-yl)ethyl]propan-2-amine

Formula: C15H22N2 Molecular weight: 230.34858 g/mol InChI Key: HQZLBYMOYCJZRF-UHFFFAOYSA-N

InChI=1S/C15H22N2/c1-4-17(12(2)3)10-9-13-11-16-15-8-6-5-7-14(13)15/h5-8,11-12,16H,4,9-10H2,1-3H3

PubChem CID: 44719455; ChemSpider: 21106305; Wikipedia: Ethylisopropyltryptamine

See also TiHKAL: #36 5-MeO-DET  
See also Chemistry notes VIII: p. 56, EIPT: Synthesis
p. 57, EIPT: GC-MS

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

5027
Analogue 6: Substituting Butyl and Methyl for Dimethyl at N

MBT
Tryptamine, N-butyl-N-methyl
Indole, 3-[2-(butylmethylamino)ethyl]
N-Butyl-N-methyltryptamine
3-[2-(Butylmethylamino)ethyl]indole

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methylbutan-1-amine

Formula: C15H22N2 Molecular weight: 230.34858 g/mol InChI Key: PUEYINPKMCBJCA-UHFFFAOYSA-N

InChI=1S/C15H22N2/c1-3-4-10-17(2)11-9-13-12-16-15-8-6-5-7-14(13)15/h5-8,12,16H,3-4,9-11H2,1-2H3

PubChem CID: 44719457; ChemSpider: 21106349; Wikipedia: Methylbutyltryptamine

See also TiHKAL: #36 5-MeO-DET  
5047
Analogue 7: Substituting Methyl and Isopropyl for Dimethyl at N

MIPT
Tryptamine, N-isopropyl-N-methyl
Indole, 3-[2-(isopropylmethylamino)ethyl]
N-Isopropyl-N-methyltryptamine
3-[2-(Isopropylmethylamino)ethyl]indole

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methylpropan-2-amine

Formula: C14H20N2 Molecular weight: 216.322 g/mol InChI Key: KTQJVAJLJZIKKD-UHFFFAOYSA-N

InChI=1S/C14H20N2/c1-11(2)16(3)9-8-12-10-15-14-7-5-4-6-13(12)14/h4-7,10-11,15H,8-9H2,1-3H3

PubChem CID: 29935323; ChemSpider: 21106353; Erowid: MIPT; Wikipedia: N-Methyl-N-isopropyltryptamine

See also TiHKAL: #10 EIPT #36 5-MeO-DET

See also Transcripts: 3.416

See also Chemistry notes VIII: p. 32, MIPT: Synthesis
p. 124, MIPT: Synthesis
p. 125, MIPT: Synthesis
p. 126, MIPT: GC-MS

Repke, DB; Grotjahn, DB; Shulgin, AT. Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents. J. Med. Chem., 1 Jan 1985, 28 (7), 892–896. 711 kB. doi:10.1021/jm00145a007

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Cozzi, NV; Shulgin, AT; Daley, PF; Gopalakrishnan, A; Anderson, LL; Feih, JT; Ruoho, AE. Psychoactive N,N-dialkyltryptamines modulate serotonin transport by at least two mechanisms. Soc. Neurosci. Abs., 1 Jan 2008, 536.17. 52 kB.

Cozzi, NV; Gopalakrishnan, A; Anderson, LL; Feih, JT; Shulgin, AT; Daley, PF; Ruoho, AE. Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter. J. Neural. Transm., 1 Dec 2009, 116 (12), 1591–1599. 420 kB. doi:10.1007/s00702-009-0308-8

5049
Analogue 8: Substituting Ethyl for Dimethyl at N

NET
N-Ethyltryptamine
Tryptamine, N-ethyl
Indole, 3-[2-(ethylamino)ethyl]
3-[2-(Ethylamino)ethyl]indole

IUPAC: N-Ethyl-2-(1H-indol-3-yl)ethan-1-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: TZWUSTVNAVKAPA-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-2-13-8-7-10-9-14-12-6-4-3-5-11(10)12/h3-6,9,13-14H,2,7-8H2,1H3

PubChem CID: 6092; ChemSpider: 5867; Wikipedia: N-Ethyltryptamine

See also TiHKAL: #6 DMT
#9 DPT
#10 EIPT
#26 LSD
See also Chemistry notes VIII: p. 52, NET: Synthesis
p. 54, NET: Synthesis
p. 55, NET: GC-MS
p. 64, NET: Synthesis
p. 65, NET: GC-MS

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

5050
Analogue 9: Substituting Methyl for Dimethyl at N

NMT
Tryptamine, N-methyl
Indole, 3-[2-(methylamino)ethyl]
N-Methyltryptamine
3-[2-(Methylamino)ethyl]indole

IUPAC: 2-(1H-Indol-3-yl)-N-methylethan-1-amine

Formula: C11H14N2 Molecular weight: 174.24226 g/mol InChI Key: NCIKQJBVUNUXLW-UHFFFAOYSA-N

InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3

PubChem CID: 6088; ChemSpider: 5863; Wikipedia: N-Methyltryptamine

See also TiHKAL: #2 DBT
#6 DMT
#27 MBT
#44 6-MeO-THH
#47 MIPT
#49 NET
#53 T
See also Chemistry notes VIII: p. 17, NMT: GC-MS
p. 22, NMT: Synthesis
p. 23, NMT: GC-MS
p. 24, NMT: GC-MS
p. 25, NMT: GC-MS
p. 26, NMT: GC-MS

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Khalil, EM; Angelis, JD; Cole, PA. Indoleamine analogs as probes of the substrate selectivity and catalytic mechanism of serotonin N-acetyltransferase. J. Biol. Chem., 13 Nov 1998, 273 (46), 30321–30327. 247 kB. doi:10.1074/jbc.273.46.30321

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine. Biomed. Chromatogr., 1 Sep 2011, 25 (9), 970–984. 1030 kB. doi:10.1002/bmc.1551

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed. Chromatogr., 1 Mar 2012, 26 (3), 301–313. 557 kB. doi:10.1002/bmc.1657

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

Gartz, J. Biotransformation of tryptamine derivatives in mycelia cultures of Psilocybe. J. Basic. Microbiol., 1989, 29 (6), 347–352. 357 kB. doi:10.1002/jobm.3620290608

Barker, SA; McIlhenny, EH; Strassman, R. A critical review of reports of endogenous psychedelic N,N-dimethyltryptamines in humans: 1955–2010. Drug Test. Anal., 2012. 270 kB. doi:10.1002/dta.422

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916):,934–937. 529 kB. doi:10.1126/science.1166127

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture: rational exploration of the underground, 5 Dec 2011.

McIlhenny, EH; Pipkin, KE; Standish, LJ; Wechkin, HA; Strassman, R; Barker, SA. Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry. J. Chromatogr. A, 18 Dec 2009, 1216 (51), 8960–8968. 450 kB. doi:10.1016/j.chroma.2009.10.088

5053
Analogue 10: Removing Dimethyl at N

T
Tryptamine
Indole, 3-(2-aminoethyl)
3-(2-Aminoethyl)indole

IUPAC: 2-(1H-Indol-3-yl)ethan-1-amine

Formula: C10H12N2 Molecular weight: 160.21568 g/mol InChI Key: APJYDQYYACXCRM-UHFFFAOYSA-N

InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2

PubChem CID: 1150; ChemSpider: 1118; Wikipedia: Tryptamine

See also TiHKAL: #2 DBT
#6 DMT
#44 6-MeO-THH
#46 5-MeS-DMT
#49 NET
See also Chemistry notes VIII: p. 21, Tryptamine: GC-MS
p. 82, Tryptamine: Synthesis

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

Martins, CPB; Awan, MA; Freeman, S; Herraiz, T; Alder, JF; Brandt, SD. Fingerprint analysis of thermolytic decarboxylation of tryptophan to tryptamine catalyzed by natural oils. J. Chromatogr. A, 7 Nov 2008, 1210 (1), 115–120. 450 kB. doi:10.1016/j.chroma.2008.09.036

Brandt, SD; Mansell, D; Freeman, S; Fleet, IA; Alder, JF. Analytical characterisation of the routes by thermolytic decarboxylation from tryptophan to tryptamine using ketone catalysts, resulting in tetrahydro-β-carboline formation. J. Pharm. Biomed. Anal., 7 Jun 2006, 41 (3), 872–882. 610 kB. doi:10.1016/j.jpba.2006.02.007

Ghosal, S; Srivastava, RS. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochemistry, 1 Jan 1973, 12 (1), 193–197. 552 kB. doi:10.1016/S0031-9422(00)84646-4

Khalil, EM; Angelis, JD; Cole, PA. Indoleamine analogs as probes of the substrate selectivity and catalytic mechanism of serotonin N-acetyltransferase. J. Biol. Chem., 13 Nov 1998, 273 (46), 30321–30327. 247 kB. doi:10.1074/jbc.273.46.30321

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

Speeter, ME; Anthony, WC. The action of oxalyl chloride on indoles: A new approach to tryptamines. J. Am. Chem. Soc., 1 Dec 1954, 76 (23), 6208–6210. 416 kB. doi:10.1021/ja01652a113

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1056 kB. doi:10.1016/0028-3908(62)90015-1

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916):,934–937. 529 kB. doi:10.1126/science.1166127

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture: rational exploration of the underground, 5 Dec 2011.

Meyers-Riggs, B. Alpha substituted tryptamines. countyourculture: rational exploration of the underground, 1 Mar 2012.

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3077 kB. doi:10.1007/BF02818560

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

5056
Analogue 11: Substituting Isopropyl for Dimethyl at N

NIPT
Tryptamine, N-isopropyl
Indole, 3-[2-(isopropylamino)ethyl]
N-Isopropyltryptamine
3-[2-(Isopropylamine)ethyl]indole

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]propan-2-amine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: QOCRVKNKLPEDCZ-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-10(2)14-8-7-11-9-15-13-6-4-3-5-12(11)13/h3-6,9-10,14-15H,7-8H2,1-2H3

PubChem CID: 45590; ChemSpider: 41480

See also TiHKAL: #4 DIPT #47 MIPT
See also Chemistry notes VIII: p. 60, NIPT: Synthesis

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

5106
Analogue 12: Substituting Methyl and Hydroxy for Dimethyl at N

N-HO-NMT
N-Hydroxy-N-methyltryptamine

IUPAC: N-Hydroxy-2-(1H-indol-3-yl)-N-methylethan-1-amine

Formula: C11H14N2O Molecular weight: 190.24166 g/mol InChI Key: UGTHUCOPOLBGRK-UHFFFAOYSA-N

InChI=1S/C11H14N2O/c1-13(14)7-6-9-8-12-11-5-3-2-4-10(9)11/h2-5,8,12,14H,6-7H2,1H3

PubChem CID: 541950; ChemSpider: 471932

See also TiHKAL: #6 DMT  
5108
Analogue 13: Substituting Cyclopropyl for Dimethyl at N

NCPT
N-Cyclopropyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]cyclopropanamine

Formula: C13H16N2 Molecular weight: 200.27954 g/mol InChI Key: VYIORSRXNBGASE-UHFFFAOYSA-N

InChI=1S/C13H16N2/c1-2-4-13-12(3-1)10(9-15-13)7-8-14-11-5-6-11/h1-4,9,11,14-15H,5-8H2

PubChem CID: 41421; ChemSpider: 37794

See also TiHKAL: #6 DMT  
5121
Analogue 14: Substituting Isopropyl and Propyl for Dimethyl at N

PIPT
N-Isopropyl-N-propyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-(propan-2-yl)propan-1-amine

Formula: C16H24N2 Molecular weight: 244.37516 g/mol InChI Key: OFXPLOPRCQJJFP-UHFFFAOYSA-N

InChI=1S/C16H24N2/c1-4-10-18(13(2)3)11-9-14-12-17-16-8-6-5-7-15(14)16/h5-8,12-13,17H,4,9-11H2,1-3H3

PubChem CID: 57464898; ChemSpider: 21106369; Wikipedia: Propylisopropyltryptamine

See also TiHKAL: #10 EIPT  
See also Chemistry notes VIII: p. 106, PIPT: Synthesis

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

5122
Analogue 15: Substituting Isopropyl and Butyl for Dimethyl at N

BIPT
N-Butyl-N-isopropyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-(propan-2-yl)butan-1-amine

Formula: C17H26N2 Molecular weight: 258.40174 g/mol InChI Key: AAFKXRUSSUPTPH-UHFFFAOYSA-N

InChI=1S/C17H26N2/c1-4-5-11-19(14(2)3)12-10-15-13-18-17-9-7-6-8-16(15)17/h6-9,13-14,18H,4-5,10-12H2,1-3H3

See also TiHKAL: #10 EIPT  
5174
Analogue 16: Substituting Ethyl and Methyl for Dimethyl at N

MET
N-Ethyl-N-methyltryptamine

IUPAC: N-Ethyl-2-(1H-indol-3-yl)-N-methylethan-1-amine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: MYEGVMLMDWYPOA-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-3-15(2)9-8-11-10-14-13-7-5-4-6-12(11)13/h4-7,10,14H,3,8-9H2,1-2H3

PubChem CID: 824845; ChemSpider: 720502; Erowid: MET; Wikipedia: Methylethyltryptamine

See also TiHKAL: #36 5-MeO-DET #47 MIPT

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

5175
Analogue 17: Substituting Propyl and Methyl for Dimethyl at N

MPT
N-Methyl-N-propyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methylpropan-1-amine

Formula: C14H20N2 Molecular weight: 216.322 g/mol InChI Key: SZUNESAKJQIJAC-UHFFFAOYSA-N

InChI=1S/C14H20N2/c1-3-9-16(2)10-8-12-11-15-14-7-5-4-6-13(12)14/h4-7,11,15H,3,8-10H2,1-2H3

See also TiHKAL: #36 5-MeO-DET #47 MIPT

See also Transcripts: 4.460

See also Chemistry notes VIII: p. 36, MPT: Synthesis

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

5182
Analogue 18: Substituting Propyl for Dimethyl at N

NPT
N-Propyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]propan-1-amine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: KBFBIAGUZWNRFI-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-2-8-14-9-7-11-10-15-13-6-4-3-5-12(11)13/h3-6,10,14-15H,2,7-9H2,1H3

PubChem CID: 45605; ChemSpider: 41495

See also TiHKAL: #9 DPT #49 NET
See also Chemistry notes VIII: p. 62, NPT: Synthesis

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

5183
Analogue 19: Substituting Butyl for Dimethyl at N

NBT
N-Butyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]butan-1-amine

Formula: C14H20N2 Molecular weight: 216.322 g/mol InChI Key: SYJRXRVYSQCOCF-UHFFFAOYSA-N

InChI=1S/C14H20N2/c1-2-3-9-15-10-8-12-11-16-14-7-5-4-6-13(12)14/h4-7,11,15-16H,2-3,8-10H2,1H3

PubChem CID: 45582; ChemSpider: 41472

See also TiHKAL: #49 NET  
5184
Analogue 20: Substituting Isobutyl for Dimethyl at N

NIBT
N-Isobutyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-2-methylpropan-1-amine

Formula: C14H20N2 Molecular weight: 216.322 g/mol InChI Key: HUZOBAFMOMZMBQ-UHFFFAOYSA-N

InChI=1S/C14H20N2/c1-11(2)9-15-8-7-12-10-16-14-6-4-3-5-13(12)14/h3-6,10-11,15-16H,7-9H2,1-2H3

PubChem CID: 45586; ChemSpider: 41476

See also TiHKAL: #49 NET  
5185
Analogue 21: Substituting sec-Butyl for Dimethyl at N

NSBT
N-sec-Butyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]butan-2-amine

Formula: C14H20N2 Molecular weight: 216.322 g/mol InChI Key: WDWNZOAFDWLAGZ-UHFFFAOYSA-N

InChI=1S/C14H20N2/c1-3-11(2)15-9-8-12-10-16-14-7-5-4-6-13(12)14/h4-7,10-11,15-16H,3,8-9H2,1-2H3

PubChem CID: 24839509; ChemSpider: 23993854

See also TiHKAL: #49 NET  
5186
Analogue 22: Substituting tert-Butyl for Dimethyl at N

NTBT
N-tert-Butyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-2-methylpropan-2-amine

Formula: C14H20N2 Molecular weight: 216.322 g/mol InChI Key: IDXHHISJIRGWJV-UHFFFAOYSA-N

InChI=1S/C14H20N2/c1-14(2,3)16-9-8-11-10-15-13-7-5-4-6-12(11)13/h4-7,10,15-16H,8-9H2,1-3H3

PubChem CID: 58980321; ChemSpider: 27128081

See also TiHKAL: #49 NET  
5187
Analogue 23: Substituting Pentyl for Dimethyl at N

NAT
N-Pentyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]pentan-1-amine

Formula: C15H22N2 Molecular weight: 230.34858 g/mol InChI Key: GSDILUUWSQHEDW-UHFFFAOYSA-N

InChI=1S/C15H22N2/c1-2-3-6-10-16-11-9-13-12-17-15-8-5-4-7-14(13)15/h4-5,7-8,12,16-17H,2-3,6,9-11H2,1H3

PubChem CID: 23336456; ChemSpider: 15259292

See also TiHKAL: #49 NET  
5188
Analogue 24: Substituting Hexyl for Dimethyl at N

NHT
N-Hexyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]hexan-1-amine

Formula: C16H24N2 Molecular weight: 244.37516 g/mol InChI Key: XWZHZQNPWLWXRN-UHFFFAOYSA-N

InChI=1S/C16H24N2/c1-2-3-4-7-11-17-12-10-14-13-18-16-9-6-5-8-15(14)16/h5-6,8-9,13,17-18H,2-4,7,10-12H2,1H3

PubChem CID: 17843698; ChemSpider: 16002090

See also TiHKAL: #2 DBT #49 NET
5372
Analogue 25: Substituting Diallyl for Dimethyl at N

DALT
Tryptamine, N,N-Diallyl
N,N-Diallyltryptamine
Indole, 3-[2-(Diallylamino)ethyl]
3-[2-(Diallylamino)ethyl]indole

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine

Formula: C16H20N2 Molecular weight: 240.3434 g/mol InChI Key: LQEATNFJCMVKAC-UHFFFAOYSA-N

InChI=1S/C16H20N2/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16/h3-8,13,17H,1-2,9-12H2

PubChem CID: 24839550; ChemSpider: 21250454; Wikipedia: DALT

See also TiHKAL: #2 DBT  
See also Chemistry notes VIII: p. 38, DALT: Synthesis; GC-MS
p. 39, DALT: GC-MS

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

5558
Analogue 26: Substituting 2-Ethoxybenzyl for Dimethyl at N

N-(2-Ethoxybenzyl)tryptamine

IUPAC: N-(2-Ethoxybenzyl)-2-(1H-indol-3-yl)ethan-1-amine

Formula: C19H22N2O Molecular weight: 294.39078 g/mol InChI Key: HDVBXBQHKIFIPF-UHFFFAOYSA-N

InChI=1S/C19H22N2O/c1-2-22-19-10-6-3-7-16(19)13-20-12-11-15-14-21-18-9-5-4-8-17(15)18/h3-10,14,20-21H,2,11-13H2,1H3

PubChem CID: 3162213; ChemSpider: 2413763

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

5559
Analogue 27: Substituting 2-Methoxyphenylethan-2-yl for Dimethyl at N

N-(2-Methoxyphenylethan-2-yl)tryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-1-(2-methoxyphenyl)ethan-1-amine

Formula: C19H22N2O Molecular weight: 294.39078 g/mol InChI Key: MANWDUANTWBBAH-UHFFFAOYSA-N

InChI=1S/C19H22N2O/c1-14(16-7-4-6-10-19(16)22-2)20-12-11-15-13-21-18-9-5-3-8-17(15)18/h3-10,13-14,20-21H,11-12H2,1-2H3

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

5564
Analogue 28: Substituting Benzyl for Dimethyl at N

N-Benzyltryptamine

IUPAC: N-Benzyl-2-(1H-indol-3-yl)ethan-1-amine

Formula: C17H18N2 Molecular weight: 250.33822 g/mol InChI Key: PRRZWJAGZHENJJ-UHFFFAOYSA-N

InChI=1S/C17H18N2/c1-2-6-14(7-3-1)12-18-11-10-15-13-19-17-9-5-4-8-16(15)17/h1-9,13,18-19H,10-12H2

PubChem CID: 45592; ChemSpider: 41482

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

5565
Analogue 29: Substituting 2-Hydroxybenzyl for Dimethyl at N

N-(2-Hydroxybenzyl)tryptamine

IUPAC: 2-({[2-(1H-Indol-3-yl)ethyl]amino}methyl)phenol

Formula: C17H18N2O Molecular weight: 266.33762 g/mol InChI Key: NUCDWASRCGAPHW-UHFFFAOYSA-N

InChI=1S/C17H18N2O/c20-17-8-4-1-5-14(17)11-18-10-9-13-12-19-16-7-3-2-6-15(13)16/h1-8,12,18-20H,9-11H2

PubChem CID: 2721617; ChemSpider: 2005549

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

5566
Analogue 30: Substituting 2-Methoxybenzyl for Dimethyl at N

N-(2-Methoxybenzyl)tryptamine

IUPAC: 2-(1H-Indol-3-yl)-N-(2-methoxybenzyl)ethan-1-amine

Formula: C18H20N2O Molecular weight: 280.3642 g/mol InChI Key: HJCSKFSDXDPIKM-UHFFFAOYSA-N

InChI=1S/C18H20N2O/c1-21-18-9-5-2-6-15(18)12-19-11-10-14-13-20-17-8-4-3-7-16(14)17/h2-9,13,19-20H,10-12H2,1H3

PubChem CID: 1988048; ChemSpider: 1511014

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. doi:10.1007/s10822-010-9400-2

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. In German.

5096
Analogue 31: Substituting Diisobutyl for Dimethyl at N

DIBT
N,N-Diisobutyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-2-methyl-N-(2-methylpropyl)propan-1-amine

Formula: C18H28N2 Molecular weight: 272.42832 g/mol InChI Key: WMLQALOMNLJRCX-UHFFFAOYSA-N

InChI=1S/C18H28N2/c1-14(2)12-20(13-15(3)4)10-9-16-11-19-18-8-6-5-7-17(16)18/h5-8,11,14-15,19H,9-10,12-13H2,1-4H3

PubChem CID: 45597; ChemSpider: 41487

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

5075
Analogue 32: Substituting Ethyl and Propyl for Dimethyl at N

EPT
N-Ethyl-N-propyltryptamine

IUPAC: N-Ethyl-N-[2-(1H-indol-3-yl)ethyl]propan-1-amine

Formula: C15H22N2 Molecular weight: 230.34858 g/mol InChI Key: LCDYRMYSOIVPRS-UHFFFAOYSA-N

InChI=1S/C15H22N2/c1-3-10-17(4-2)11-9-13-12-16-15-8-6-5-7-14(13)15/h5-8,12,16H,3-4,9-11H2,1-2H3

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

5463
Analogue 33: Substituting Isobutyl and Methyl for Dimethyl at N

MIBT

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N,2-dimethylpropan-1-amine

Formula: C15H22N2 Molecular weight: 230.34858 g/mol InChI Key: SOTPLIRCHUNUNF-UHFFFAOYSA-N

InChI=1S/C15H22N2/c1-12(2)11-17(3)9-8-13-10-16-15-7-5-4-6-14(13)15/h4-7,10,12,16H,8-9,11H2,1-3H3

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5475
Analogue 34: Substituting sec-Butyl and Methyl for Dimethyl at N

MSBT

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methylbutan-2-amine

Formula: C15H22N2 Molecular weight: 230.34858 g/mol InChI Key: JFDFFCIYMLHPFQ-UHFFFAOYSA-N

InChI=1S/C15H22N2/c1-4-12(2)17(3)10-9-13-11-16-15-8-6-5-7-14(13)15/h5-8,11-12,16H,4,9-10H2,1-3H3

See also Chemistry notes VIII: p. 34, MSBT: Synthesis; GC-MS
p. 35, MSBT: GC-MS
5476
Analogue 35: Substituting Di-sec-butyl for Dimethyl at N

DSBT

IUPAC: N-(Butan-2-yl)-N-[2-(1H-indol-3-yl)ethyl]butan-2-amine

Formula: C18H28N2 Molecular weight: 272.42832 g/mol InChI Key: GAMSOQVPHIMBSR-UHFFFAOYSA-N

InChI=1S/C18H28N2/c1-5-14(3)20(15(4)6-2)12-11-16-13-19-18-10-8-7-9-17(16)18/h7-10,13-15,19H,5-6,11-12H2,1-4H3

See also Chemistry notes VIII: p. 58, DSBT: Synthesis
p. 59, DSBT: GC-MS
5477
Analogue 36: Substituting Formyl for Dimethyl at N

N-Formyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]formamide

Formula: C11H12N2O Molecular weight: 188.22578 g/mol InChI Key: JQWVVJKFXINLNV-UHFFFAOYSA-N

InChI=1S/C11H12N2O/c14-8-12-6-5-9-7-13-11-4-2-1-3-10(9)11/h1-4,7-8,13H,5-6H2,(H,12,14)

ChemSpider: 1361749

See also Chemistry notes VIII: p. 19, N-Formyltryptamine: Synthesis
p. 20, N-Formyltryptamine: GC-MS
5601
Analogue 37: Substituting Methyl and Benzyl for Dimethyl at N

IUPAC: N-Benzyl-2-(1H-indol-3-yl)-N-methylethan-1-amine

Formula: C18H20N2 Molecular weight: 264.3648 g/mol InChI Key: SULYXIDYHIHCJJ-UHFFFAOYSA-N

InChI=1S/C18H20N2/c1-20(14-15-7-3-2-4-8-15)12-11-16-13-19-18-10-6-5-9-17(16)18/h2-10,13,19H,11-12,14H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5602
Analogue 38: Substituting Methyl and 4-Bromobenzyl for Dimethyl at N

IUPAC: N-(4-Bromobenzyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine

Formula: C18H19BrN2 Molecular weight: 343.26086 g/mol InChI Key: TVAVLVVYWUVROV-UHFFFAOYSA-N

InChI=1S/C18H19BrN2/c1-21(13-14-6-8-16(19)9-7-14)11-10-15-12-20-18-5-3-2-4-17(15)18/h2-9,12,20H,10-11,13H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5603
Analogue 39: Substituting Methyl and 2-Phenylethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-methyl-N-(2-phenylethyl)ethan-1-amine

Formula: C19H22N2 Molecular weight: 278.39138 g/mol InChI Key: UEJDDSOAXSHQBL-UHFFFAOYSA-N

InChI=1S/C19H22N2/c1-21(13-11-16-7-3-2-4-8-16)14-12-17-15-20-19-10-6-5-9-18(17)19/h2-10,15,20H,11-14H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5604
Analogue 40: Substituting Methyl and 2-(2-Methylphenyl)ethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-methyl-N-[2-(2-methylphenyl)ethyl]ethan-1-amine

Formula: C20H24N2 Molecular weight: 292.41796 g/mol InChI Key: DVSIGAAWMHMHBI-UHFFFAOYSA-N

InChI=1S/C20H24N2/c1-16-7-3-4-8-17(16)11-13-22(2)14-12-18-15-21-20-10-6-5-9-19(18)20/h3-10,15,21H,11-14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5605
Analogue 41: Substituting Methyl and 2-(2-Fluorophenyl)ethyl for Dimethyl at N

IUPAC: 2-(2-Fluorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C19H21FN2 Molecular weight: 296.3818432 g/mol InChI Key: HWHITXZOLDVIMF-UHFFFAOYSA-N

InChI=1S/C19H21FN2/c1-22(12-10-15-6-2-4-8-18(15)20)13-11-16-14-21-19-9-5-3-7-17(16)19/h2-9,14,21H,10-13H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5606
Analogue 42: Substituting Methyl and 2-(2-Chlorophenyl)ethyl for Dimethyl at N

IUPAC: 2-(2-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C19H21ClN2 Molecular weight: 312.83644 g/mol InChI Key: ZFAVMQBJQUVWJV-UHFFFAOYSA-N

InChI=1S/C19H21ClN2/c1-22(12-10-15-6-2-4-8-18(15)20)13-11-16-14-21-19-9-5-3-7-17(16)19/h2-9,14,21H,10-13H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5607
Analogue 43: Substituting Methyl and 2-(2,5-Dimethylphenyl)ethyl for Dimethyl at N

IUPAC: 2-(2,5-Dimethylphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C21H26N2 Molecular weight: 306.44454 g/mol InChI Key: DWEQILHXCVUFEA-UHFFFAOYSA-N

InChI=1S/C21H26N2/c1-16-8-9-17(2)18(14-16)10-12-23(3)13-11-19-15-22-21-7-5-4-6-20(19)21/h4-9,14-15,22H,10-13H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5608
Analogue 44: Substituting Methyl and 2-(2-Methoxyphenyl)ethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-[2-(2-methoxyphenyl)ethyl]-N-methylethan-1-amine

Formula: C20H24N2O Molecular weight: 308.41736 g/mol InChI Key: NWDJCTJKWOZBLQ-UHFFFAOYSA-N

InChI=1S/C20H24N2O/c1-22(13-11-16-7-3-6-10-20(16)23-2)14-12-17-15-21-19-9-5-4-8-18(17)19/h3-10,15,21H,11-14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5609
Analogue 45: Substituting Methyl and 2-(2,5-Dimethoxyphenyl)ethyl for Dimethyl at N

IUPAC: 2-(2,5-Dimethoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C21H26N2O2 Molecular weight: 338.44334 g/mol InChI Key: JPJUVPFNTLRLRR-UHFFFAOYSA-N

InChI=1S/C21H26N2O2/c1-23(12-10-16-14-18(24-2)8-9-21(16)25-3)13-11-17-15-22-20-7-5-4-6-19(17)20/h4-9,14-15,22H,10-13H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5610
Analogue 46: Substituting Methyl and 2-(2,6-Dichlorophenyl)ethyl for Dimethyl at N

IUPAC: 2-(2,6-Dichlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C19H20Cl2N2 Molecular weight: 347.2815 g/mol InChI Key: AJLKBALCKXZUNH-UHFFFAOYSA-N

InChI=1S/C19H20Cl2N2/c1-23(12-10-16-17(20)6-4-7-18(16)21)11-9-14-13-22-19-8-3-2-5-15(14)19/h2-8,13,22H,9-12H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5611
Analogue 47: Substituting Methyl and 2-(3-Methylphenyl)ethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-methyl-N-[2-(3-methylphenyl)ethyl]ethan-1-amine

Formula: C20H24N2 Molecular weight: 292.41796 g/mol InChI Key: UAZDTRBRTLYJBO-UHFFFAOYSA-N

InChI=1S/C20H24N2/c1-16-6-5-7-17(14-16)10-12-22(2)13-11-18-15-21-20-9-4-3-8-19(18)20/h3-9,14-15,21H,10-13H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5612
Analogue 48: Substituting Methyl and 2-(3-Acetoxyphenyl)ethyl for Dimethyl at N

IUPAC: 3-(2-{[2-(1H-Indol-3-yl)ethyl](methyl)amino}ethyl)phenyl acetate

Formula: C21H24N2O2 Molecular weight: 336.42746 g/mol InChI Key: JSTRUOIJOOUWTJ-UHFFFAOYSA-N

InChI=1S/C21H24N2O2/c1-16(24)25-19-7-5-6-17(14-19)10-12-23(2)13-11-18-15-22-21-9-4-3-8-20(18)21/h3-9,14-15,22H,10-13H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5613
Analogue 49: Substituting Methyl and 2-(3-Methoxyphenyl)ethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-[2-(3-methoxyphenyl)ethyl]-N-methylethan-1-amine

Formula: C20H24N2O Molecular weight: 308.41736 g/mol InChI Key: WVNPOYRYRQPFAD-UHFFFAOYSA-N

InChI=1S/C20H24N2O/c1-22(12-10-16-6-5-7-18(14-16)23-2)13-11-17-15-21-20-9-4-3-8-19(17)20/h3-9,14-15,21H,10-13H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5614
Analogue 50: Substituting Methyl and 2-(3-Chlorophenyl)ethyl for Dimethyl at N

IUPAC: 2-(3-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C19H21ClN2 Molecular weight: 312.83644 g/mol InChI Key: XRKDSJKJHWHYRD-UHFFFAOYSA-N

InChI=1S/C19H21ClN2/c1-22(11-9-15-5-4-6-17(20)13-15)12-10-16-14-21-19-8-3-2-7-18(16)19/h2-8,13-14,21H,9-12H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5615
Analogue 51: Substituting Methyl and 2-(3-Bromophenyl)ethyl for Dimethyl at N

IUPAC: 2-(3-Bromophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C19H21BrN2 Molecular weight: 357.28744 g/mol InChI Key: IUBVNRXXSWJOCY-UHFFFAOYSA-N

InChI=1S/C19H21BrN2/c1-22(11-9-15-5-4-6-17(20)13-15)12-10-16-14-21-19-8-3-2-7-18(16)19/h2-8,13-14,21H,9-12H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5616
Analogue 52: Substituting Methyl and 2-(3,5-Dimethylphenyl)ethyl for Dimethyl at N

IUPAC: 2-(3,5-Dimethylphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C21H26N2 Molecular weight: 306.44454 g/mol InChI Key: MPWWYBZATGVIKL-UHFFFAOYSA-N

InChI=1S/C21H26N2/c1-16-12-17(2)14-18(13-16)8-10-23(3)11-9-19-15-22-21-7-5-4-6-20(19)21/h4-7,12-15,22H,8-11H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5617
Analogue 53: Substituting Methyl and 2-(3,4-Dimethoxyphenyl)ethyl for Dimethyl at N

IUPAC: 2-(3,4-Dimethoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C21H26N2O2 Molecular weight: 338.44334 g/mol InChI Key: JECHAUWDLLDLKO-UHFFFAOYSA-N

InChI=1S/C21H26N2O2/c1-23(12-10-16-8-9-20(24-2)21(14-16)25-3)13-11-17-15-22-19-7-5-4-6-18(17)19/h4-9,14-15,22H,10-13H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5618
Analogue 54: Substituting Methyl and 2-(3,4-Dichlorophenyl)ethyl for Dimethyl at N

IUPAC: 2-(3,4-Dichlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C19H20Cl2N2 Molecular weight: 347.2815 g/mol InChI Key: PEOLSGZSWXEFAW-UHFFFAOYSA-N

InChI=1S/C19H20Cl2N2/c1-23(10-8-14-6-7-17(20)18(21)12-14)11-9-15-13-22-19-5-3-2-4-16(15)19/h2-7,12-13,22H,8-11H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5619
Analogue 55: Substituting Methyl and 2-(4-Methylphenyl)ethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-methyl-N-[2-(4-methylphenyl)ethyl]ethan-1-amine

Formula: C20H24N2 Molecular weight: 292.41796 g/mol InChI Key: CHPMMTFFDOCALR-UHFFFAOYSA-N

InChI=1S/C20H24N2/c1-16-7-9-17(10-8-16)11-13-22(2)14-12-18-15-21-20-6-4-3-5-19(18)20/h3-10,15,21H,11-14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5620
Analogue 56: Substituting Methyl and 2-(4-Methoxyphenyl)ethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-[2-(4-methoxyphenyl)ethyl]-N-methylethan-1-amine

Formula: C20H24N2O Molecular weight: 308.41736 g/mol InChI Key: JSKDTSUBDZJHNK-UHFFFAOYSA-N

InChI=1S/C20H24N2O/c1-22(13-11-16-7-9-18(23-2)10-8-16)14-12-17-15-21-20-6-4-3-5-19(17)20/h3-10,15,21H,11-14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5621
Analogue 57: Substituting Methyl and 2-(4-Fluorophenyl)ethyl for Dimethyl at N

IUPAC: 2-(4-Fluorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C19H21FN2 Molecular weight: 296.3818432 g/mol InChI Key: OYUXUMISKIAYHP-UHFFFAOYSA-N

InChI=1S/C19H21FN2/c1-22(12-10-15-6-8-17(20)9-7-15)13-11-16-14-21-19-5-3-2-4-18(16)19/h2-9,14,21H,10-13H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5622
Analogue 58: Substituting Methyl and 2-(4-Chlorophenyl)ethyl for Dimethyl at N

IUPAC: 2-(4-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C19H21ClN2 Molecular weight: 312.83644 g/mol InChI Key: KWGPHEHTUZAGEW-UHFFFAOYSA-N

InChI=1S/C19H21ClN2/c1-22(12-10-15-6-8-17(20)9-7-15)13-11-16-14-21-19-5-3-2-4-18(16)19/h2-9,14,21H,10-13H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5623
Analogue 59: Substituting Methyl and 2-(4-Bromophenyl)ethyl for Dimethyl at N

IUPAC: 2-(4-Bromophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C19H21BrN2 Molecular weight: 357.28744 g/mol InChI Key: LRYJCZDYTISZCG-UHFFFAOYSA-N

InChI=1S/C19H21BrN2/c1-22(12-10-15-6-8-17(20)9-7-15)13-11-16-14-21-19-5-3-2-4-18(16)19/h2-9,14,21H,10-13H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5624
Analogue 60: Substituting Methyl and 2-(4-Nitrophenyl)ethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-methyl-N-[2-(4-nitrophenyl)ethyl]ethan-1-amine

Formula: C19H21N3O2 Molecular weight: 323.38894 g/mol InChI Key: WEHBXEXLUVTUMK-UHFFFAOYSA-N

InChI=1S/C19H21N3O2/c1-21(12-10-15-6-8-17(9-7-15)22(23)24)13-11-16-14-20-19-5-3-2-4-18(16)19/h2-9,14,20H,10-13H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5625
Analogue 61: Substituting Methyl and 2-(4-Phenylphenyl)ethyl for Dimethyl at N

IUPAC: 2-(Biphenyl-4-yl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C25H26N2 Molecular weight: 354.48734 g/mol InChI Key: IXJLELADIIMMKI-UHFFFAOYSA-N

InChI=1S/C25H26N2/c1-27(18-16-23-19-26-25-10-6-5-9-24(23)25)17-15-20-11-13-22(14-12-20)21-7-3-2-4-8-21/h2-14,19,26H,15-18H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5626
Analogue 62: Substituting Methyl and Indole-3-ylethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C21H23N3 Molecular weight: 317.42742 g/mol InChI Key: YXCCIJFWMRIURI-UHFFFAOYSA-N

InChI=1S/C21H23N3/c1-24(12-10-16-14-22-20-8-4-2-6-18(16)20)13-11-17-15-23-21-9-5-3-7-19(17)21/h2-9,14-15,22-23H,10-13H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5627
Analogue 63: Substituting Methyl and 5-Methoxyindole-3-ylethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine

Formula: C22H25N3O Molecular weight: 347.4534 g/mol InChI Key: PLLDTQXECIBZDT-UHFFFAOYSA-N

InChI=1S/C22H25N3O/c1-25(11-9-16-14-23-21-6-4-3-5-19(16)21)12-10-17-15-24-22-8-7-18(26-2)13-20(17)22/h3-8,13-15,23-24H,9-12H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5628
Analogue 64: Substituting Methyl and Naphthalen-1-ylethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-methyl-N-[2-(naphthalen-1-yl)ethyl]ethan-1-amine

Formula: C23H24N2 Molecular weight: 328.45006 g/mol InChI Key: GXFCBPXCJQIHKD-UHFFFAOYSA-N

InChI=1S/C23H24N2/c1-25(16-14-20-17-24-23-12-5-4-11-22(20)23)15-13-19-9-6-8-18-7-2-3-10-21(18)19/h2-12,17,24H,13-16H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5629
Analogue 65: Substituting Methyl and Naphthalen-2-ylethyl for Dimethyl at N

IUPAC: 2-(1H-Indol-3-yl)-N-methyl-N-[2-(naphthalen-2-yl)ethyl]ethan-1-amine

Formula: C23H24N2 Molecular weight: 328.45006 g/mol InChI Key: VPZIUHDOTMQZPK-UHFFFAOYSA-N

InChI=1S/C23H24N2/c1-25(15-13-21-17-24-23-9-5-4-8-22(21)23)14-12-18-10-11-19-6-2-3-7-20(19)16-18/h2-11,16-17,24H,12-15H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5630
Analogue 66: Substituting Methyl and Phenylpropyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-phenylpropan-1-amine

Formula: C20H24N2 Molecular weight: 292.41796 g/mol InChI Key: NSSNOHRWZJNPEZ-UHFFFAOYSA-N

InChI=1S/C20H24N2/c1-22(14-7-10-17-8-3-2-4-9-17)15-13-18-16-21-20-12-6-5-11-19(18)20/h2-6,8-9,11-12,16,21H,7,10,13-15H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5631
Analogue 67: Substituting Methyl and 3-(3,4,5-Trimethoxyphenyl)propyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-(3,4,5-trimethoxyphenyl)propan-1-amine

Formula: C23H30N2O3 Molecular weight: 382.4959 g/mol InChI Key: WWHKBANXYLFOPK-UHFFFAOYSA-N

InChI=1S/C23H30N2O3/c1-25(13-11-18-16-24-20-10-6-5-9-19(18)20)12-7-8-17-14-21(26-2)23(28-4)22(15-17)27-3/h5-6,9-10,14-16,24H,7-8,11-13H2,1-4H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5632
Analogue 68: Substituting Methyl and Phenylbutyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-4-phenylbutan-1-amine

Formula: C21H26N2 Molecular weight: 306.44454 g/mol InChI Key: PDDXHMQTTYDFEF-UHFFFAOYSA-N

InChI=1S/C21H26N2/c1-23(15-8-7-11-18-9-3-2-4-10-18)16-14-19-17-22-21-13-6-5-12-20(19)21/h2-6,9-10,12-13,17,22H,7-8,11,14-16H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5633
Analogue 69: Substituting Methyl and Phenylthiopropyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-(phenylsulfanyl)propan-1-amine

Formula: C20H24N2S Molecular weight: 324.48296 g/mol InChI Key: JPJJBMXETQLEMA-UHFFFAOYSA-N

InChI=1S/C20H24N2S/c1-22(13-7-15-23-18-8-3-2-4-9-18)14-12-17-16-21-20-11-6-5-10-19(17)20/h2-6,8-11,16,21H,7,12-15H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5634
Analogue 70: Substituting Methyl and Pentyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methylpentan-1-amine

Formula: C16H24N2 Molecular weight: 244.37516 g/mol InChI Key: ZHXAQRYGNJUXFY-UHFFFAOYSA-N

InChI=1S/C16H24N2/c1-3-4-7-11-18(2)12-10-14-13-17-16-9-6-5-8-15(14)16/h5-6,8-9,13,17H,3-4,7,10-12H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5635
Analogue 71: Substituting Methyl and Hexyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methylhexan-1-amine

Formula: C17H26N2 Molecular weight: 258.40174 g/mol InChI Key: GIRXPGMUAQWECH-UHFFFAOYSA-N

InChI=1S/C17H26N2/c1-3-4-5-8-12-19(2)13-11-15-14-18-17-10-7-6-9-16(15)17/h6-7,9-10,14,18H,3-5,8,11-13H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5636
Analogue 72: Substituting Methyl and Heptyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methylheptan-1-amine

Formula: C18H28N2 Molecular weight: 272.42832 g/mol InChI Key: KZSKMMOYLNQRJX-UHFFFAOYSA-N

InChI=1S/C18H28N2/c1-3-4-5-6-9-13-20(2)14-12-16-15-19-18-11-8-7-10-17(16)18/h7-8,10-11,15,19H,3-6,9,12-14H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5637
Analogue 73: Substituting Methyl and Octyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methyloctan-1-amine

Formula: C19H30N2 Molecular weight: 286.4549 g/mol InChI Key: HMWJKNHNUKCRTB-UHFFFAOYSA-N

InChI=1S/C19H30N2/c1-3-4-5-6-7-10-14-21(2)15-13-17-16-20-19-12-9-8-11-18(17)19/h8-9,11-12,16,20H,3-7,10,13-15H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5638
Analogue 74: Substituting Methyl and Dodecyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methyldodecan-1-amine

Formula: C23H38N2 Molecular weight: 342.56122 g/mol InChI Key: ZSUYQMLIHRWGFI-UHFFFAOYSA-N

InChI=1S/C23H38N2/c1-3-4-5-6-7-8-9-10-11-14-18-25(2)19-17-21-20-24-23-16-13-12-15-22(21)23/h12-13,15-16,20,24H,3-11,14,17-19H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5639
Analogue 75: Substituting Methyl and Tetraadecyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methyltetradecan-1-amine

Formula: C25H42N2 Molecular weight: 370.61438 g/mol InChI Key: FHTZCOZCPQIUPB-UHFFFAOYSA-N

InChI=1S/C25H42N2/c1-3-4-5-6-7-8-9-10-11-12-13-16-20-27(2)21-19-23-22-26-25-18-15-14-17-24(23)25/h14-15,17-18,22,26H,3-13,16,19-21H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5640
Analogue 76: Substituting Methyl and Octadecyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methyloctadecan-1-amine

Formula: C29H50N2 Molecular weight: 426.7207 g/mol InChI Key: NFZVROXSQYAETL-UHFFFAOYSA-N

InChI=1S/C29H50N2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-24-31(2)25-23-27-26-30-29-22-19-18-21-28(27)29/h18-19,21-22,26,30H,3-17,20,23-25H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5641
Analogue 77: Substituting Methyl and Cyclopropylmethyl for Dimethyl at N

IUPAC: N-(Cyclopropylmethyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine

Formula: C15H20N2 Molecular weight: 228.3327 g/mol InChI Key: SGKGVNOWUGAWGN-UHFFFAOYSA-N

InChI=1S/C15H20N2/c1-17(11-12-6-7-12)9-8-13-10-16-15-5-3-2-4-14(13)15/h2-5,10,12,16H,6-9,11H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5642
Analogue 78: Substituting Methyl and Cyclopentylmethyl for Dimethyl at N

IUPAC: N-(Cyclopentylmethyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine

Formula: C17H24N2 Molecular weight: 256.38586 g/mol InChI Key: SBXVSTIADWCRLY-UHFFFAOYSA-N

InChI=1S/C17H24N2/c1-19(13-14-6-2-3-7-14)11-10-15-12-18-17-9-5-4-8-16(15)17/h4-5,8-9,12,14,18H,2-3,6-7,10-11,13H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5643
Analogue 79: Substituting Methyl and Cyclohexylmethyl for Dimethyl at N

IUPAC: N-(Cyclohexylmethyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine

Formula: C18H26N2 Molecular weight: 270.41244 g/mol InChI Key: CGJVKTLFWMUSFH-UHFFFAOYSA-N

InChI=1S/C18H26N2/c1-20(14-15-7-3-2-4-8-15)12-11-16-13-19-18-10-6-5-9-17(16)18/h5-6,9-10,13,15,19H,2-4,7-8,11-12,14H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5645
Analogue 80: Substituting Methyl and Pentan-3-ylmethyl for Dimethyl at N

IUPAC: 2-Ethyl-N-[2-(1H-indol-3-yl)ethyl]-N-methylbutan-1-amine

Formula: C17H26N2 Molecular weight: 258.40174 g/mol InChI Key: IQNCFANRDPMJAO-UHFFFAOYSA-N

InChI=1S/C17H26N2/c1-4-14(5-2)13-19(3)11-10-15-12-18-17-9-7-6-8-16(15)17/h6-9,12,14,18H,4-5,10-11,13H2,1-3H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5646
Analogue 81: Substituting Methyl and Allyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methylprop-2-en-1-amine

Formula: C14H18N2 Molecular weight: 214.30612 g/mol InChI Key: GXCLVBGFBYZDAG-UHFFFAOYSA-N

InChI=1S/C14H18N2/c1-3-9-16(2)10-8-12-11-15-14-7-5-4-6-13(12)14/h3-7,11,15H,1,8-10H2,2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5647
Analogue 82: Substituting Methyl and Prop-1-ynyl for Dimethyl at N

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-methylprop-2-yn-1-amine

Formula: C14H16N2 Molecular weight: 212.29024 g/mol InChI Key: VHDFVGYDYUFWEY-UHFFFAOYSA-N

InChI=1S/C14H16N2/c1-3-9-16(2)10-8-12-11-15-14-7-5-4-6-13(12)14/h1,4-7,11,15H,8-10H2,2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5648
Analogue 83: Substituting Methyl and Cyclohexylpropyl for Dimethyl at N

IUPAC: 3-Cyclohexyl-N-[2-(1H-indol-3-yl)ethyl]-N-methylpropan-1-amine

Formula: C20H30N2 Molecular weight: 298.4656 g/mol InChI Key: STLADHLRUOOGMD-UHFFFAOYSA-N

InChI=1S/C20H30N2/c1-22(14-7-10-17-8-3-2-4-9-17)15-13-18-16-21-20-12-6-5-11-19(18)20/h5-6,11-12,16-17,21H,2-4,7-10,13-15H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5649
Analogue 84: Substituting Methyl and 3-Phenylprop-2-enyl for Dimethyl at N

IUPAC: (2E)-N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-phenylprop-2-en-1-amine

Formula: C20H22N2 Molecular weight: 290.40208 g/mol InChI Key: DDNORTQHAFNTAF-JXMROGBWSA-N

InChI=1S/C20H22N2/c1-22(14-7-10-17-8-3-2-4-9-17)15-13-18-16-21-20-12-6-5-11-19(18)20/h2-12,16,21H,13-15H2,1H3/b10-7+

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5650
Analogue 85: Substituting Methyl and 2-Methoxy-2-oxoethyl for Dimethyl at N

IUPAC: Methyl N-[2-(1H-indol-3-yl)ethyl]-N-methylglycinate

Formula: C14H18N2O2 Molecular weight: 246.30492 g/mol InChI Key: PKCOBBDWDYFWCI-UHFFFAOYSA-N

InChI=1S/C14H18N2O2/c1-16(10-14(17)18-2)8-7-11-9-15-13-6-4-3-5-12(11)13/h3-6,9,15H,7-8,10H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5651
Analogue 86: Substituting Methyl and 2-tertButoxy-2-oxoethyl for Dimethyl at N

IUPAC: tert-Butyl N-[2-(1H-indol-3-yl)ethyl]-N-methylglycinate

Formula: C17H24N2O2 Molecular weight: 288.38466 g/mol InChI Key: VTRBOWNJMZSCTO-UHFFFAOYSA-N

InChI=1S/C17H24N2O2/c1-17(2,3)21-16(20)12-19(4)10-9-13-11-18-15-8-6-5-7-14(13)15/h5-8,11,18H,9-10,12H2,1-4H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5652
Analogue 87: Substituting Methyl and 2-Amino-2-oxoethyl for Dimethyl at N

IUPAC: N2-[2-(1H-Indol-3-yl)ethyl]-N2-methylglycinamide

Formula: C13H17N3O Molecular weight: 231.29358 g/mol InChI Key: AZBNKAKVIWJFJT-UHFFFAOYSA-N

InChI=1S/C13H17N3O/c1-16(9-13(14)17)7-6-10-8-15-12-5-3-2-4-11(10)12/h2-5,8,15H,6-7,9H2,1H3,(H2,14,17)

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5653
Analogue 88: Substituting Methyl and 2-Cyanoethyl for Dimethyl at N

IUPAC: 3-{[2-(1H-Indol-3-yl)ethyl](methyl)amino}propanenitrile

Formula: C14H17N3 Molecular weight: 227.30488 g/mol InChI Key: KSPYEYZODRWCLB-UHFFFAOYSA-N

InChI=1S/C14H17N3/c1-17(9-4-8-15)10-7-12-11-16-14-6-3-2-5-13(12)14/h2-3,5-6,11,16H,4,7,9-10H2,1H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5654
Analogue 89: Substituting Methyl and 2-Acetoxyethyl for Dimethyl at N

IUPAC: 2-{[2-(1H-Indol-3-yl)ethyl](methyl)amino}ethyl acetate

Formula: C15H20N2O2 Molecular weight: 260.3315 g/mol InChI Key: NGYRPKJDYAJVFJ-UHFFFAOYSA-N

InChI=1S/C15H20N2O2/c1-12(18)19-10-9-17(2)8-7-13-11-16-15-6-4-3-5-14(13)15/h3-6,11,16H,7-10H2,1-2H3

PubChem CID: 68541087

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

5495
Analogue 90: Substituting Dipentyl for Dimethyl at N

DAT
N,N-Diamyltryptamine
N,N-Dipentyltryptamine

IUPAC: N-[2-(1H-Indol-3-yl)ethyl]-N-pentylpentan-1-amine

Formula: C20H32N2 Molecular weight: 300.48148 g/mol InChI Key: AXUJSLZQVYSFBL-UHFFFAOYSA-N

InChI=1S/C20H32N2/c1-3-5-9-14-22(15-10-6-4-2)16-13-18-17-21-20-12-8-7-11-19(18)20/h7-8,11-12,17,21H,3-6,9-10,13-16H2,1-2H3

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1056 kB. doi:10.1016/0028-3908(62)90015-1

5496
Analogue 91: Substituting Dihexyl for Dimethyl at N

DHT
N,N-Dihexyltryptamine

IUPAC: N-Hexyl-N-[2-(1H-indol-3-yl)ethyl]hexan-1-amine

Formula: C22H36N2 Molecular weight: 328.53464 g/mol InChI Key: GTQCUMXNKPVMON-UHFFFAOYSA-N

InChI=1S/C22H36N2/c1-3-5-7-11-16-24(17-12-8-6-4-2)18-15-20-19-23-22-14-10-9-13-21(20)22/h9-10,13-14,19,23H,3-8,11-12,15-18H2,1-2H3

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1056 kB. doi:10.1016/0028-3908(62)90015-1

5743
Analogue 92: Substituting Hydroxy for Dimethyl at N

HOT-T

IUPAC: N-Hydroxy-1-(1H-indol-3-yl)propan-2-amine

Formula: C11H14N2O Molecular weight: 190.24166 g/mol InChI Key: QDEFFOYILHFBSE-UHFFFAOYSA-N

InChI=1S/C11H14N2O/c1-8(13-14)6-9-7-12-11-5-3-2-4-10(9)11/h2-5,7-8,12-14H,6H2,1H3

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

One N+ analogue:
5232
Analogue 1: Adding Oxo at N+

DMT N-oxide

IUPAC: [2-(1H-Indol-3-yl)ethyl]dimethylamine oxide

Formula: C12H16N2O Molecular weight: 204.26824 g/mol InChI Key: FSRSWKRQDYWUFG-UHFFFAOYSA-N

InChI=1S/C12H16N2O/c1-14(2,15)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3

PubChem CID: 5316905; ChemSpider: 4475872; Wikipedia: Dimethyltryptamine-N-oxide

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine. Biomed. Chromatogr., 1 Sep 2011, 25 (9), 970–984. 1030 kB. doi:10.1002/bmc.1551

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed. Chromatogr., 1 Mar 2012, 26 (3), 301–313. 557 kB. doi:10.1002/bmc.1657

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

McIlhenny, EH; Pipkin, KE; Standish, LJ; Wechkin, HA; Strassman, R; Barker, SA. Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry. J. Chromatogr. A, 18 Dec 2009, 1216 (51), 8960–8968. 450 kB. doi:10.1016/j.chroma.2009.10.088

One α analogue:
5116
Analogue 1: Adding Methyl at α

α,N,N-TMT
α,N,N-Trimethyltryptamine

IUPAC: 1-(1H-Indol-3-yl)-N,N-dimethylpropan-2-amine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: XQFCCTPWINMCQJ-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-10(15(2)3)8-11-9-14-13-7-5-4-6-12(11)13/h4-7,9-10,14H,8H2,1-3H3

Wikipedia: Alpha-N,N-Trimethyltryptamine

See also TiHKAL: #8 α,N-DMT  

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

Two R1 analogues:
5111
Analogue 1: Adding Methyl at R1

1-Me-DMT
N,N,1-TMT
N,N,1-Trimethyltryptamine

IUPAC: N,N-Dimethyl-2-(1-methyl-1H-indol-3-yl)ethan-1-amine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: WYFWKMQPMCPKLZ-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-14(2)9-8-11-10-15(3)13-7-5-4-6-12(11)13/h4-7,10H,8-9H2,1-3H3

PubChem CID: 25927; ChemSpider: 24156

See also TiHKAL: #6 DMT  

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

5112
Analogue 2: Adding Methoxy at R1

1-MeO-DMT
Lespedamine
1-Methoxy-N,N-dimethyltryptamine

IUPAC: 2-(1-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: DXTZTYQDNUHCAB-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-14(2)9-8-11-10-15(16-3)13-7-5-4-6-12(11)13/h4-7,10H,8-9H2,1-3H3

PubChem CID: 11138594; ChemSpider: 9313707

See also TiHKAL: #6 DMT  
One R2 analogue:
5034
Analogue 1: Adding Methyl at R2

2-Me-DMT
2,N,N-TMT
Desmethoxy-Indapex
Tryptamine, 2,N,N-trimethyl
Indole, 3-[2-(dimethylamino)ethyl]-2-methyl
2,N,N-Trimethyltryptamine
3-[2-(Dimethylamino)ethyl]-2-methylindole

IUPAC: N,N-Dimethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: NDGCOWDSLVNLGE-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-10-11(8-9-15(2)3)12-6-4-5-7-13(12)14-10/h4-7,14H,8-9H2,1-3H3

PubChem CID: 11820174; ChemSpider: 9994827; Wikipedia: 2,N,N-TMT

See also TiHKAL: #6 DMT #7 2,α-DMT

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

Glennon, RA; Lee, M; Rangisetty, JB; Dukat, M; Roth, BL; Savage, JE; McBridge, A; Rauser, L; Hufeisen, SJ; Lee, DKH. 2-Substituted tryptamines: Agents with selectivity for 5-HT6 serotonin receptors. J. Med. Chem., 9 Mar 2000, 43 (5), 1011–1018. 137 kB. doi:10.1021/jm990550b

Nine R4 analogues:
5018
Analogue 1: Adding Hydroxy at R4

4-HO-DMT
CX-59
PSOH
Psilocin
Tryptamine, 4-hydroxy-N,N-dimethyl
4-Indolol, 3-[2-(dimethylamino)ethyl]
N,N-Dimethyl-4-hydroxytryptamine
3-[2-(Dimethylamino)ethyl]-4-indolol

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol

Formula: C12H16N2O Molecular weight: 204.26824 g/mol InChI Key: SPCIYGNTAMCTRO-UHFFFAOYSA-N

InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3

PubChem CID: 4980; ChemSpider: 4807; Drugs Forum: 4-HO-DMT; Erowid: Psilocybin & Psilocin; Wikipedia: Psilocin

See also TiHKAL: #16 4-HO-DET
#19 5-HO-DMT
#20 4-HO-DPT
#21 4-HO-MET
#22 4-HO-MIPT
#23 4-HO-MPT
#24 4-HO-pyr-T
#26 LSD
#31 5,6-MDO-DMT
#39 4-MeO-MIPT
#47 MIPT
#56 5-MeO-DALT

See also Transcripts: 2.292, 5.680

See also Pharmacology notes II: p. 292, Psilocin

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Gartz, J. Extraction and analysis of indole derivatives from fungal biomass. J. Basic. Microbiol., 1994, 34 (1), 17–22. 614 kB. doi:10.1002/jobm.3620340104

Meyers-Riggs, B. 4-Hydroxy tryptamines. countyourculture: rational exploration of the underground, 7 Jul 2012.

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Sarwar, M; McDonald, JL. A rapid extraction and GC/MS methodology for the identification of psilocyn in mushroom/chocolate concoctions. Microgram J., 1 Jul 2003, 1 (3–4), 177–183. 211 kB.

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Heim, R; Genest, K; Hughes, DW; Belec, G. Botanical and chemical characterisation of a forensic mushroom specimen of the genus psilocybe. J. Forensic Sci. Soc., 1 Jul 1966, 6 (4), 192–201. 2094 kB. doi:10.1016/S0015-7368(66)70336-3

Hofmann, A; Heim, R; Brack, A; Kobel, H; Frey, A; Ott, H; Petrzilka, T; Troxler, F. Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen. Helv. Chim. Acta, 1959, 42 (5), 1557–1572. 1132 kB. doi:10.1002/hlca.19590420518

Troxler, F; Seemann, F; Hofmann, A. Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen. Helv. Chim. Acta, 1959, 42 (6), 2073–2103. 1589 kB. doi:10.1002/hlca.19590420638

Chilton, WS; Bigwood, J; Jensen, RE. Psilocin, Bufotenine and serotonin: Historical and biosynthetic observations. J. Psychoactive Drugs, 1 Jan 1979, 11 (1–2), 61–69. 9523 kB. doi:10.1080/02791072.1979.10472093

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Migliaccio, GP; Shieh, TN; Byrn, SR; Hathaway, BA; Nichols, DE. Comparison of solution conformational preferences for the hallucinogens bufotenin and psilocin using 360-MHz proton NMR spectroscopy. J. Med. Chem., 1 Feb 1981, 24 (2), 206–209. 564 kB. doi:10.1021/jm00134a016

Morris, H. Blood Spore: Of Murder and Mushrooms. Harper’s Magazine, 1 Jul 2013, 41–56. 13834 kB.

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Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture: rational exploration of the underground, 5 Dec 2011.

Meyers-Riggs, B. Biosynthesis of 4-substituted tryptamine derivatives. countyourculture: rational exploration of the underground, 17 Feb 2012.

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Gross, ST. Detecting psychoactive drugs in the developmental stages of mushrooms. J. Forensic Sci., 1 May 2000, 45 (3), 527–537. 6189 kB. doi:10.1520/JFS14725J

Gross, ST. Psychotropic drugs in developmental mushrooms: A case study review. J. Forensic Sci., 1 Nov 2002, 47 (6), 1–5. 369 kB. doi:10.1520/JFS15564J

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Pellegrini, M; Rotolo, MC; Marchei, E; Pacifici, R; Saggio, F; Pichini, S. Magic truffles or philosopher’s stones: a legal way to sell psilocybin? Drug Test. Anal., 1 Mar 2013, 5 (3), 182–185. 219 kB. doi:10.1002/dta.1400

5058
Analogue 2: Adding Phosphoryloxy at R4

4-H2PO4-DMT
4-HO-DMT phosphate ester
CY-39
PSOP
Psilocybin
Psilocin, phosphate ester
Tryptamine, N,N-dimethyl-4-phosphoryloxy
4-Indolol, 3-[2-(dimethylamino)ethyl], phosphate ester
N,N-Dimethyl-4-phosphoryloxytryptamine
3-[2-(Dimethylamino)ethyl]-4-indolol, phosphate ester

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate

Formula: C12H17N2O4P Molecular weight: 284.248141 g/mol InChI Key: QVDSEJDULKLHCG-UHFFFAOYSA-N

InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)

PubChem CID: 10624; ChemSpider: 10178; Drugs Forum: 4-H2PO4-DMT; Erowid: Psilocybin & Psilocin; Wikipedia: Psilocybin

See also PiHKAL: #40 2C-T-2
#41 2C-T-4
#127 METHYL-DOB
#132 MMDA
See also TiHKAL: #16 4-HO-DET
#19 5-HO-DMT
#22 4-HO-MIPT
#26 LSD
#30 4,5-MDO-DMT
#31 5,6-MDO-DMT
#46 5-MeS-DMT
#48 α-MT

See also Transcripts: 1.187, 2.323.4, 2.323.5, 3.400, 3.401, 3.402, 5.680

See also Pharmacology notes I: p. 187, Psilocybin
See also Pharmacology notes II: app. 5, Untitled

Wark, C. A social and cultural history of the federal prohibition of psilocybin. Ph. D. Thesis, University of Missouri-Columbia, Columbia, MO, 1 Aug 2007. 2183 kB.

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. doi:10.1016/j.bmcl.2005.06.104

Meyers-Riggs, B. 4-Hydroxy tryptamines. countyourculture: rational exploration of the underground, 7 Jul 2012.

Nichols, DE. Commentary on: Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance by Griffiths et al. Psychopharmacology, 1 Aug 2006, 187 (3), 284–286. 71 kB. doi:10.1007/s00213-006-0458-4

Gartz, J. Extraction and analysis of indole derivatives from fungal biomass. J. Basic. Microbiol., 1994, 34 (1), 17–22. 614 kB. doi:10.1002/jobm.3620340104

Hofmann, A; Heim, R; Brack, A; Kobel, H; Frey, A; Ott, H; Petrzilka, T; Troxler, F. Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen. Helv. Chim. Acta, 1959, 42 (5), 1557–1572. 1132 kB. doi:10.1002/hlca.19590420518

Troxler, F; Seemann, F; Hofmann, A. Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen. Helv. Chim. Acta, 1959, 42 (6), 2073–2103. 1589 kB. doi:10.1002/hlca.19590420638

Griffiths, RR; Richards, WA; McCann, U; Jesse, R. Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. Psychopharmacology, 1 Aug 2006, 187 (3), 268–283. 342 kB. doi:10.1007/s00213-006-0457-5

Morris, H. Blood Spore: Of Murder and Mushrooms. Harper’s Magazine, 1 Jul 2013, 41–56. 13834 kB.

Rodriguez-Cruz, SE. Analysis and characterization of psilocybin and psilocin using liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS) with collision-induced-dissociation (CID) and source-induced-dissociation (SID). Microgram J., 1 Jul 2005, 3 (3–4), 175–182. 560 kB.

Wiseman-Distler, MH; Sourkes, TL. The effect of 4-hydroxyindoles on the metabolism of 5-hydroxytryptamine (serotonin). Ann. N.Y. Acad. Sci., 1 Jan 1962, 96, 142–151. 458 kB. doi:10.1111/j.1749-6632.1962.tb50109.x

Pellegrini, M; Rotolo, MC; Marchei, E; Pacifici, R; Saggio, F; Pichini, S. Magic truffles or philosopher’s stones: a legal way to sell psilocybin? Drug Test. Anal., 1 Mar 2013, 5 (3), 182–185. 219 kB. doi:10.1002/dta.1400

Heim, R; Genest, K; Hughes, DW; Belec, G. Botanical and chemical characterisation of a forensic mushroom specimen of the genus psilocybe. J. Forensic Sci. Soc., 1 Jul 1966, 6 (4), 192–201. 2094 kB. doi:10.1016/S0015-7368(66)70336-3

Gouzoulis-Mayfrank, E. Differential actions of an entactogen compared to a stimulant and a hallucinogen in healthy humans. In Heffter Review; Nichols, DE, Ed., Heffter Research Institute, Santa Fe, NM, 2001; Vol. 2, pp 64–72. 261 kB.

Passie, T; Seifert, J; Schneider, U; Emrich, HM. The pharmacology of psilocybin. Addict. Biol., 1 Jan 2002, 7 (4), 357–364. 184 kB. doi:10.1080/135562102100000593

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Bunch, KS. Psilocybin and spiritual experience. Psy. D. Thesis, Alliant International University, San Francisco, CA, USA, 1 Aug 2009. 5715 kB.

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3077 kB. doi:10.1007/BF02818560

Shulgin, AT. Psilocybe mushroom extractions. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 5 Mar 2003.

Shulgin, AT. Drug testing for mushrooms. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 1 Dec 2004.

Leung, AY; Paul, AG. Baeocystin and norbaeocystin: New analogs of psilocybin from Psilocybe baeocystis. J. Pharm. Sci., 1 Jan 1968, 57 (10), 1667–1671. 399 kB. doi:10.1002/jps.2600571007

Nichols, DE; Frescas, SP. Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin. Synthesis, 1 Jan 1999, 1999, 935–938. 1481 kB. doi:10.1055/s-1999-3490

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture: rational exploration of the underground, 5 Dec 2011.

Shulgin, AT. Profiles of psychedelic drugs. 8. Psilocybin. J. Psychedelic Drugs, 1 Jan 1980, 12 (1), 79. 1595 kB. doi:10.1080/02791072.1980.10471557

Vollenweider, FX; Kometer, M. The neurobiology of psychedelic drugs: implications for the treatment of mood disorders. Nat. Rev. Neurosci., 1 Sep 2010, 11 (9), 642–651. 588 kB. doi:10.1038/nrn2884

Agurell, S; Nilsson, JLG. Biosynthesis of psilocybin. Part II. Incorporation of labelled tryptamine derivatives. Acta Chem. Scand., 1 Jan 1968, 22 (4), 1210–1218. 805 kB. doi:10.3891/acta.chem.scand.22-1210

Gross, ST. Psychotropic drugs in developmental mushrooms: A case study review. J. Forensic Sci., 1 Nov 2002, 47 (6), 1–5. 369 kB. doi:10.1520/JFS15564J

Gross, ST. Detecting psychoactive drugs in the developmental stages of mushrooms. J. Forensic Sci., 1 May 2000, 45 (3), 527–537. 6189 kB. doi:10.1520/JFS14725J

5153
Analogue 3: Adding Methoxy at R4

4-MeO-DMT
PSOM
4-Methoxy-N,N-dimethyltryptamine

IUPAC: 2-(4-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: HFYHBTWTJDAYGW-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2)8-7-10-9-14-11-5-4-6-12(16-3)13(10)11/h4-6,9,14H,7-8H2,1-3H3

PubChem CID: 12017578; ChemSpider: 23126449; Drugs Forum: 4-MeO-DMT; Wikipedia: 4-MeO-DMT

See also TiHKAL: #39 4-MeO-MIPT #46 5-MeS-DMT

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

5171
Analogue 4: Adding Methylthio at R4

4-MeS-DMT
N,N-Dimethyl-4-methylthiotryptamine

IUPAC: N,N-Dimethyl-2-[4-(methylsulfanyl)-1H-indol-3-yl]ethan-1-amine

Formula: C13H18N2S Molecular weight: 234.36042 g/mol InChI Key: YWCOPJQNWPEWQP-UHFFFAOYSA-N

InChI=1S/C13H18N2S/c1-15(2)8-7-10-9-14-11-5-4-6-12(16-3)13(10)11/h4-6,9,14H,7-8H2,1-3H3

PubChem CID: 21180; ChemSpider: 167880

See also TiHKAL: #46 5-MeS-DMT  

Kline, TB; Benington, F; Morin, RD; Beaton, JM; Glennon, RA; Domelsmith, LN; Houk, KN; Rozeboom, MD. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives. J. Med. Chem., 1 Jan 1982, 25 (11), 1381–1383. 378 kB. doi:10.1021/jm00353a021

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

5370
Analogue 5: Adding Acetoxy at R4

4-AcO-DMT
4-Acetoxy-DMT
PSOA
Psilacetin
4-Acetoxy-N,N-dimethyltryptamine

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl acetate

Formula: C14H18N2O2 Molecular weight: 246.30492 g/mol InChI Key: RTLRUOSYLFOFHV-UHFFFAOYSA-N

InChI=1S/C14H18N2O2/c1-10(17)18-13-6-4-5-12-14(13)11(9-15-12)7-8-16(2)3/h4-6,9,15H,7-8H2,1-3H3

PubChem CID: 15429212; ChemSpider: 21106357; Drugs Forum: 4-AcO-DMT; Erowid: 4-Acetoxy-DMT; Wikipedia: O-Acetylpsilocin

See also TiHKAL: #19 5-HO-DMT  

Nichols, DE; Frescas, SP. Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin. Synthesis, 1 Jan 1999, 1999, 935–938. 1481 kB. doi:10.1055/s-1999-3490

Meyers-Riggs, B. 4-Hydroxy tryptamines. countyourculture: rational exploration of the underground, 7 Jul 2012.

5223
Analogue 6: Adding Amino at R4

4-Amino-DMT

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-amine

Formula: C12H17N3 Molecular weight: 203.28348 g/mol InChI Key: LRLDHGFFSHPWME-UHFFFAOYSA-N

InChI=1S/C12H17N3/c1-15(2)7-6-9-8-14-11-5-3-4-10(13)12(9)11/h3-5,8,14H,6-7,13H2,1-2H3

PubChem CID: 57438418

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Mckay, JB; Parkhursrt, RM; Silversteinax, M; Skinne, DWA. Analogues of psilocin and lysergic acid diethylamide. I. Chloro, nitro, and amino derivatives of 3-substituted indoles. Can. J. Chem., 1 Jan 1963, 41 (10), 2585–2590. 249 kB. doi:10.1139/v63-378

5226
Analogue 7: Adding Fluoro at R4

4-F-DMT

IUPAC: 2-(4-Fluoro-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15FN2 Molecular weight: 206.2593032 g/mol InChI Key: ISJZKVWGUWBUFG-UHFFFAOYSA-N

InChI=1S/C12H15FN2/c1-15(2)7-6-9-8-14-11-5-3-4-10(13)12(9)11/h3-5,8,14H,6-7H2,1-2H3

PubChem CID: 11492162; ChemSpider: 9666968

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. doi:10.1016/j.bmcl.2005.06.104

Blair, JB; Kurrasch-Orbaugh, D; Marona-Lewicka, D; Cumbay, MG; Watts, VJ; Barker, EL; Nichols, DE. Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines. J. Med. Chem., 1 Jan 2000, 43 (24), 4701–4710. 494 kB. doi:10.1021/jm000339w

Blair, JB. Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 1997. 3251 kB.

5483
Analogue 8: Adding Chloro at R4

IUPAC: 2-(4-Chloro-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15ClN2 Molecular weight: 222.7139 g/mol InChI Key: JLGAFYIPWQMGPG-UHFFFAOYSA-N

InChI=1S/C12H15ClN2/c1-15(2)7-6-9-8-14-11-5-3-4-10(13)12(9)11/h3-5,8,14H,6-7H2,1-2H3

PubChem CID: 23373080

Mckay, JB; Parkhursrt, RM; Silversteinax, M; Skinne, DWA. Analogues of psilocin and lysergic acid diethylamide. I. Chloro, nitro, and amino derivatives of 3-substituted indoles. Can. J. Chem., 1 Jan 1963, 41 (10), 2585–2590. 249 kB. doi:10.1139/v63-378

5484
Analogue 9: Adding Nitro at R4

IUPAC: N,N-Dimethyl-2-(4-nitro-1H-indol-3-yl)ethan-1-amine

Formula: C12H15N3O2 Molecular weight: 233.2664 g/mol InChI Key: ZDIYDYYEQOZCGA-UHFFFAOYSA-N

InChI=1S/C12H15N3O2/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)15(16)17/h3-5,8,13H,6-7H2,1-2H3

Mckay, JB; Parkhursrt, RM; Silversteinax, M; Skinne, DWA. Analogues of psilocin and lysergic acid diethylamide. I. Chloro, nitro, and amino derivatives of 3-substituted indoles. Can. J. Chem., 1 Jan 1963, 41 (10), 2585–2590. 249 kB. doi:10.1139/v63-378

15 R5 analogues:
5019
Analogue 1: Adding Hydroxy at R5

5-HO-DMT
N,N-Dimethylserotonin
Bufotenine
Mappine
Tryptamine, N,N-dimethyl-5-hydroxy
Indol-5-ol, 3-[2-(dimethylamino)ethyl]
N,N-Dimethyl-5-hydroxytryptamine
3-(2-Dimethylaminoethyl)indol-5-ol

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol

Formula: C12H16N2O Molecular weight: 204.26824 g/mol InChI Key: VTTONGPRPXSUTJ-UHFFFAOYSA-N

InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

PubChem CID: 10257; ChemSpider: 9839; Erowid: Bufotenin; Wikipedia: Bufotenin

See also TiHKAL: #3 DET
#5 α,O-DMS
#6 DMT
#35 Melatonin
#38 5-MeO-DMT

Chilton, WS; Bigwood, J; Jensen, RE. Psilocin, Bufotenine and serotonin: Historical and biosynthetic observations. J. Psychoactive Drugs, 1 Jan 1979, 11 (1–2), 61–69. 9523 kB. doi:10.1080/02791072.1979.10472093

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

McIlhenny, EH; Pipkin, KE; Standish, LJ; Wechkin, HA; Strassman, R; Barker, SA. Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry. J. Chromatogr. A, 18 Dec 2009, 1216 (51), 8960–8968. 450 kB. doi:10.1016/j.chroma.2009.10.088

Migliaccio, GP; Shieh, TN; Byrn, SR; Hathaway, BA; Nichols, DE. Comparison of solution conformational preferences for the hallucinogens bufotenin and psilocin using 360-MHz proton NMR spectroscopy. J. Med. Chem., 1 Feb 1981, 24 (2), 206–209. 564 kB. doi:10.1021/jm00134a016

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine. Biomed. Chromatogr., 1 Sep 2011, 25 (9), 970–984. 1030 kB. doi:10.1002/bmc.1551

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed. Chromatogr., 1 Mar 2012, 26 (3), 301–313. 557 kB. doi:10.1002/bmc.1657

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

Blackledge, RD; Phelan, CP. Identification of bufotenine in Yopo seeds via GC/IRD. Microgram J., 1 Jan 2006, 4 (1–4), 3–11. 334 kB.

Lyttle, T; Goldstein, D; Gartz, J. Bufo toads and bufotenine: Fact and fiction surrounding an alleged psychedelic. J. Psychoactive Drugs, 1 Sep 1996, 28 (3), 267–290. 24650 kB. doi:10.1080/02791072.1996.10472488

Barker, SA; McIlhenny, EH; Strassman, R. A critical review of reports of endogenous psychedelic N,N-dimethyltryptamines in humans: 1955–2010. Drug Test. Anal., 2012. 270 kB. doi:10.1002/dta.422

McBride, MC. Bufotenine: Toward an understanding of possible psychoactive mechanisms. J. Psychoactive Drugs, 1 Jan 2000, 32 (3), 321–331. 1639 kB. doi:10.1080/02791072.2000.10400456

Ott, J. Pharmanopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine. J. Psychoactive Drugs, 1 Sep 2001, 33 (3), 273–281. 1158 kB. doi:10.1080/02791072.2001.10400574

Urban, JD; Clarke, WP; Zastrow, M; Nichols, DE; Kobilka, B; Weinstein, H; Javitch, JA; Roth, BL; Christopoulos, A; Sexton, PM; Miller, KJ; . Functional selectivity and classical concepts of quantitative pharmacology. J. Pharmacol. Exp. Ther., 1 Jan 2007, 320 (1), 1–13. 506 kB. doi:10.1124/jpet.106.104463

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3077 kB. doi:10.1007/BF02818560

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Ciprian-Ollivier, J; Cetkovich-Bakmas, MG. Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr. Res., 19 Dec 1997, 28 (2–3), 257–265. 722 kB. doi:10.1039/S0920-9964(97)00116-3

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Shulgin, AT. Profiles of psychedelic drugs. 11. Bufotenine. J. Psychoactive Drugs, 1 Jan 1981, 13 (4), 389. 848 kB. doi:10.1080/02791072.1981.10471899

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

5038
Analogue 2: Adding Methoxy at R5

5-MeO-DMT
N,N,O-TMS
OMB
Tryptamine, 5-methoxy-N,N-dimethyl
Indole, 5-methoxy-3-[2-(dimethylamino)ethyl]
5-Methoxy-N,N-dimethyltryptamine
5-Methoxy-3-[2-(dimethylamino)ethyl]indole
N,N,O-Trimethylserotonin
Bufotenine methyl ether
O-Methylbufotenine

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: ZSTKHSQDNIGFLM-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

PubChem CID: 1832; ChemSpider: 1766; Erowid: 5-MeO-DMT; Wikipedia: 5-MeO-DMT

See also TiHKAL: #6 DMT
#7 2,α-DMT
#10 EIPT
#13 Harmaline
#19 5-HO-DMT
#31 5,6-MDO-DMT
#35 Melatonin
#36 5-MeO-DET
#39 4-MeO-MIPT
#40 5-MeO-MIPT
#42 5-MeO-NMT
#43 5-MeO-pyr-T
#45 5-MeO-TMT
#46 5-MeS-DMT
#50 NMT

See also Transcripts: 1.194, 1.195, 2.298, 2.323.4

See also Pharmacology notes I: p. 194, 5-MeO-DMT
p. 195, 5-MeO-DMT
See also Pharmacology notes II: app. 4, Experiment for Death Valley
p. 298, 5-MeO-DMT

McIlhenny, EH; Pipkin, KE; Standish, LJ; Wechkin, HA; Strassman, R; Barker, SA. Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry. J. Chromatogr. A, 18 Dec 2009, 1216 (51), 8960–8968. 450 kB. doi:10.1016/j.chroma.2009.10.088

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. doi:10.1021/jm950498t

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Halberstadt, AL; Nichols, DE; Geyer, MA. Behavioral effects of α,α,β,β-tetradeutero-5-MeO-DMT in rats: comparison with 5-MeO-DMT administered in combination with a monoamine oxidase inhibitor. Psychopharmacology, 1 Jun 2012, 221 (4), 709–218. 296 kB. doi:10.1007/s00213-011-2616-6

Barker, SA; McIlhenny, EH; Strassman, R. A critical review of reports of endogenous psychedelic N,N-dimethyltryptamines in humans: 1955–2010. Drug Test. Anal., 2012. 270 kB. doi:10.1002/dta.422

Glennon, RA; Lee, M; Rangisetty, JB; Dukat, M; Roth, BL; Savage, JE; McBridge, A; Rauser, L; Hufeisen, SJ; Lee, DKH. 2-Substituted tryptamines: Agents with selectivity for 5-HT6 serotonin receptors. J. Med. Chem., 9 Mar 2000, 43 (5), 1011–1018. 137 kB. doi:10.1021/jm990550b

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 2008, 54 (1), 89–96. 1882 kB. doi:10.1248/jhs.54.89

Shen, H; Jiang, X; Winter, JC; Yu, A. Psychedelic 5-methoxy-N,N-dimethyltryptamine: Metabolism, pharmacokinetics, drug interactions, and pharmacological actions. Curr. Drug Metab., 1 Oct 2010, 11 (8), 659–666. 589 kB. doi:10.2174/138920010794233495

Schmid, CL; Bohn, LM. Serotonin, but not N-methyltryptamines, activates the serotonin 2A receptor via a β-arrestin2/Src/Akt signaling complex in vivo. J. Neurosci., 6 Oct 2010, 30 (40), 13513–13524. 1534 kB. doi:10.1523/JNEUROSCI.1665-10.2010

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Benington, F; Morin, RD; Clark, LC. Synthesis of O- and N-methylated derivatives of 5-hydroxytryptamine. J. Org. Chem., 1 Dec 1958, 23 (12), 1977–1979. 401 kB. doi:10.1021/jo01106a046

Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines. Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB.

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed. Chromatogr., 1 Mar 2012, 26 (3), 301–313. 557 kB. doi:10.1002/bmc.1657

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine. Biomed. Chromatogr., 1 Sep 2011, 25 (9), 970–984. 1030 kB. doi:10.1002/bmc.1551

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Brandt, SD; Tearavarich, R; Dempster, N; Cozzi, NV; Daley, PF. Synthesis and characterization of 5-methoxy-2-methyl-N,N-dialkylated tryptamines. Drug Test. Anal., 1 Jan 2012, 4 (1), 24–32. 506 kB. doi:10.1002/dta.398

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Callaway, JC; Grob, CS; McKenna, DJ; Nichols, DE; Shulgin, AT; Tupper, KW; Sklerov, JH; Levine, B; Moore, KA. A demand for clarity regarding a case report on the ingestion of 5-methoxy-N, N-Dimethyltryptamine (5-MeO-DMT) in an Ayahuasca preparation. J. Anal. Toxicol., 1 Jul 2006, 30 (6), 406–407. 53 kB. doi:10.1093/jat/30.6.406

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Winter, JC; Filipink, RA; Timineri, D; Helsley, SE; Rabin, RA. The paradox of 5-methoxy-N,N-dimethyltryptamine: an indoleamine hallucinogen that induces stimulus control via 5-HT1A receptors. Pharmacol. Biochem. Behav., 1 Jan 2000, 65 (1), 75–82. 157 kB. doi:10.1016/S0091-3057(99)00178-1

Kline, TB; Benington, F; Morin, RD; Beaton, JM; Glennon, RA; Domelsmith, LN; Houk, KN; Rozeboom, MD. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives. J. Med. Chem., 1 Jan 1982, 25 (11), 1381–1383. 378 kB. doi:10.1021/jm00353a021

Ciprian-Ollivier, J; Cetkovich-Bakmas, MG. Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr. Res., 19 Dec 1997, 28 (2–3), 257–265. 722 kB. doi:10.1039/S0920-9964(97)00116-3

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Glennon, RA; Titeler, M; Lyon, RA; Slusher, RM. N,N-Di-n-propylserotonin: Binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. J. Med. Chem., 1 Jan 1988, 31 (4), 867–870. 600 kB. doi:10.1021/jm00399a031

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Macor, JE; Fox, CB; Johnson, C; Koe, BK; Lebel, LA; Zorn, SH. 1-(2-Aminoethyl)-3-methyl-8,9-dihydropyrano[3,2-e]indole: A rotationally restricted phenolic analog of the neurotransmitter serotonin and agonist selective for serotonin (5-HT2-type) receptors. J. Med. Chem., 1 Jan 1992, 35 (20), 3625–3632. 1944 kB. doi:10.1021/jm00098a005

5046
Analogue 3: Adding Methylthio at R5

5-MeS-DMT
Tryptamine, N,N-dimethyl-5-methylthio
Indole, 3-[2-(dimethylamino)ethyl]-5-methylthio
N,N-Dimethyl-5-methylthiotryptamine
3-[2-(Dimethylamino)ethyl]-5-methylthioindole

IUPAC: N,N-Dimethyl-2-[5-(methylsulfanyl)-1H-indol-3-yl]ethan-1-amine

Formula: C13H18N2S Molecular weight: 234.36042 g/mol InChI Key: YOGJZQGRTVMCPY-UHFFFAOYSA-N

InChI=1S/C13H18N2S/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

PubChem CID: 21180; ChemSpider: 19917; Wikipedia: 5-MeS-DMT

See also Transcripts: 3.343

Kline, TB; Benington, F; Morin, RD; Beaton, JM; Glennon, RA; Domelsmith, LN; Houk, KN; Rozeboom, MD. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives. J. Med. Chem., 1 Jan 1982, 25 (11), 1381–1383. 378 kB. doi:10.1021/jm00353a021

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

5113
Analogue 4: Adding Bromo at R5

5-Br-DMT
5-Bromo-N,N-dimethyltryptamine

IUPAC: 2-(5-Bromo-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15BrN2 Molecular weight: 267.1649 g/mol InChI Key: ATEYZYQLBQUZJE-UHFFFAOYSA-N

InChI=1S/C12H15BrN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3

PubChem CID: 360252; ChemSpider: 319812; Wikipedia: 5-Bromo-DMT

See also TiHKAL: #6 DMT  

Morris, H; Wallach, J. Sea DMT: God Molecule or Barnacle Repellent? Vice, 26 Mar 2013.

Matzdorf, T. 5-Carboxamidotryptamin-derivate als liganden für 5-HT7- und 5-HT2A-rezeptoren: synthese und in-vitro-pharmakologie. Ph. D. Thesis, Universität Regensburg, Berlin, Germany, 23 Jan 2009. 1011 kB.

5129
Analogue 5: Adding Sulfoxy at R5

Bufoviridine
N,N-Dimethyl-5-sulfoxytryptamine

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl hydrogen sulfate

Formula: C12H16N2O4S Molecular weight: 284.33144 g/mol InChI Key: OYOOWLVMRZQOMJ-UHFFFAOYSA-N

InChI=1S/C12H16N2O4S/c1-14(2)6-5-9-8-13-12-4-3-10(7-11(9)12)18-19(15,16)17/h3-4,7-8,13H,5-6H2,1-2H3,(H,15,16,17)

See also TiHKAL: #19 5-HO-DMT  
5130
Analogue 6: Adding Ethoxy at R5

5-EtO-DMT
5-Ethoxy-N,N-dimethyltryptamine

IUPAC: 2-(5-Ethoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C14H20N2O Molecular weight: 232.3214 g/mol InChI Key: OSUDCFCSUHGWJF-UHFFFAOYSA-N

InChI=1S/C14H20N2O/c1-4-17-12-5-6-14-13(9-12)11(10-15-14)7-8-16(2)3/h5-6,9-10,15H,4,7-8H2,1-3H3

PubChem CID: 57468316; ChemSpider: 26286732; Wikipedia: 5-Ethoxy-DMT

See also TiHKAL: #19 5-HO-DMT  

Tearavarich, R; Hahnvajanawong, V; Dempster, N; Daley, PF; Cozzi, NV; Brandt, SD. Microwave-accelerated preparation and analytical characterization of 5-ethoxy-N,N-dialkyl-[α,α,β,β-H4]- and [α,α,β,β-D4]-tryptamines. Drug Test. Anal., 1 Sep 2011, 3 (9), 597–608. 253 kB. doi:10.1002/dta.223

5132
Analogue 7: Adding Acetoxy at R5

5-AcO-DMT
5-Acetoxy-N,N-dimethyltryptamine

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl acetate

Formula: C14H18N2O2 Molecular weight: 246.30492 g/mol InChI Key: BZFGYTBVFYYKOK-UHFFFAOYSA-N

InChI=1S/C14H18N2O2/c1-10(17)18-12-4-5-14-13(8-12)11(9-15-14)6-7-16(2)3/h4-5,8-9,15H,6-7H2,1-3H3

PubChem CID: 15480709; ChemSpider: 23194786

See also TiHKAL: #19 5-HO-DMT  

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. doi:10.1021/jm950498t

5374
Analogue 8: Adding Methyl at R5

5,N,N-TMT
5,N,N-Trimethyltryptamine
N,N,5-Trimethyltryptamine

IUPAC: N,N-Dimethyl-2-(5-methyl-1H-indol-3-yl)ethan-1-amine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: NCGJLYBZSJSCIC-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-10-4-5-13-12(8-10)11(9-14-13)6-7-15(2)3/h4-5,8-9,14H,6-7H2,1-3H3

PubChem CID: 1837; ChemSpider: 1771; Wikipedia: 5,N,N-TMT

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Benington, F; Morin, RD; Clark, LC. Synthesis of some 5- and 6-chloro, 5-methyl, and 5,6,7-trimethyl derivatives of tryptamine. J. Org. Chem., 1 Sep 1960, 25 (9), 1542–1547. 857 kB. doi:10.1021/jo01079a020

Shulgin, AT. 5-Me-DMT or 5,N,N-TMT (5,N,N-trimethyltryptamine). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 18 Nov 2002.

5085
Analogue 9: Adding Methylaminosulfonylmethyl at R5

Sumatriptan

IUPAC: 1-{3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide

Formula: C14H21N3O2S Molecular weight: 295.40044 g/mol InChI Key: KQKPFRSPSRPDEB-UHFFFAOYSA-N

InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3

PubChem CID: 5358; ChemSpider: 5165

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. doi:10.1021/jm950498t

5227
Analogue 10: Adding Fluoro at R5

5-F-DMT

IUPAC: 2-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15FN2 Molecular weight: 206.2593032 g/mol InChI Key: BXYDWQABVPBLBU-UHFFFAOYSA-N

InChI=1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3

PubChem CID: 2762738; ChemSpider: 2043436

Blair, JB; Kurrasch-Orbaugh, D; Marona-Lewicka, D; Cumbay, MG; Watts, VJ; Barker, EL; Nichols, DE. Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines. J. Med. Chem., 1 Jan 2000, 43 (24), 4701–4710. 494 kB. doi:10.1021/jm000339w

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

Blair, JB. Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 1997. 3251 kB.

5708
Analogue 11: Adding Ethyl at R5

5-Et-DMT

IUPAC: 2-(5-Ethyl-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C14H20N2 Molecular weight: 216.322 g/mol InChI Key: ZEHXYLDGQMEYAX-UHFFFAOYSA-N

InChI=1S/C14H20N2/c1-4-11-5-6-14-13(9-11)12(10-15-14)7-8-16(2)3/h5-6,9-10,15H,4,7-8H2,1-3H3

PubChem CID: 10775128; ChemSpider: 8950441

Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. doi:10.1021/jm950498t

5644
Analogue 12: Adding Chloro at R5

5-Chloro-DMT

IUPAC: 2-(5-Chloro-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15ClN2 Molecular weight: 222.7139 g/mol InChI Key: LXATUVRMTAHHDX-UHFFFAOYSA-N

InChI=1S/C12H15ClN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3

Benington, F; Morin, RD; Clark, LC. Synthesis of some 5- and 6-chloro, 5-methyl, and 5,6,7-trimethyl derivatives of tryptamine. J. Org. Chem., 1 Sep 1960, 25 (9), 1542–1547. 857 kB. doi:10.1021/jo01079a020

5904
Analogue 13: Adding Trimethylsilyl at R5

IUPAC: N,N-Dimethyl-2-[5-(trimethylsilyl)-1H-indol-3-yl]ethan-1-amine

Formula: C15H24N2Si Molecular weight: 260.44996 g/mol InChI Key: RXCODBRXQPTBAZ-UHFFFAOYSA-N

InChI=1S/C15H24N2Si/c1-17(2)9-8-12-11-16-15-7-6-13(10-14(12)15)18(3,4)5/h6-7,10-11,16H,8-9H2,1-5H3

Matzdorf, T. 5-Carboxamidotryptamin-derivate als liganden für 5-HT7- und 5-HT2A-rezeptoren: synthese und in-vitro-pharmakologie. Ph. D. Thesis, Universität Regensburg, Berlin, Germany, 23 Jan 2009. 1011 kB.

5900
Analogue 14: Adding Acetyl at R5

IUPAC: 1-{3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}ethanone

Formula: C14H18N2O Molecular weight: 230.30552 g/mol InChI Key: LMCPLRMTEPSADY-UHFFFAOYSA-N

InChI=1S/C14H18N2O/c1-10(17)11-4-5-14-13(8-11)12(9-15-14)6-7-16(2)3/h4-5,8-9,15H,6-7H2,1-3H3

Matzdorf, T. 5-Carboxamidotryptamin-derivate als liganden für 5-HT7- und 5-HT2A-rezeptoren: synthese und in-vitro-pharmakologie. Ph. D. Thesis, Universität Regensburg, Berlin, Germany, 23 Jan 2009. 1011 kB.

5882
Analogue 15: Adding Carbamoyl at R5

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indole-5-carboxamide

Formula: C13H17N3O Molecular weight: 231.29358 g/mol InChI Key: KPXCJBKYEUTWOF-UHFFFAOYSA-N

InChI=1S/C13H17N3O/c1-16(2)6-5-10-8-15-12-4-3-9(13(14)17)7-11(10)12/h3-4,7-8,15H,5-6H2,1-2H3,(H2,14,17)

Matzdorf, T. 5-Carboxamidotryptamin-derivate als liganden für 5-HT7- und 5-HT2A-rezeptoren: synthese und in-vitro-pharmakologie. Ph. D. Thesis, Universität Regensburg, Berlin, Germany, 23 Jan 2009. 1011 kB.

Eight R6 analogues:
5102
Analogue 1: Adding Hydroxy at R6

6-HO-DMT
6-Hydroxy-N,N-dimethyltryptamine

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-6-ol

Formula: C12H16N2O Molecular weight: 204.26824 g/mol InChI Key: WUQMRWPLIMXBDX-UHFFFAOYSA-N

InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-7-10(15)3-4-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

PubChem CID: 15124; ChemSpider: 14396

See also TiHKAL: #3 DET #41 5,6-MeO-MIPT

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1056 kB. doi:10.1016/0028-3908(62)90015-1

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. doi:10.1016/j.bmcl.2005.06.104

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

5154
Analogue 2: Adding Methoxy at R6

6-MeO-DMT
6-Methoxy-N,N-dimethyltryptamine

IUPAC: 2-(6-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: AWOWBKXVYZRYSP-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-8-11(16-3)4-5-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

PubChem CID: 12017579; ChemSpider: 23118889

See also TiHKAL: #39 4-MeO-MIPT #54 Tetrahydroharmine

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

5225
Analogue 3: Adding Fluoro at R6

6-F-DMT

IUPAC: 2-(6-Fluoro-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15FN2 Molecular weight: 206.2593032 g/mol InChI Key: DZXZPVGWRZCXDH-UHFFFAOYSA-N

InChI=1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-7-10(13)3-4-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3

ChemSpider: 26286731

Blair, JB. Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 1997. 3251 kB.

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

Blair, JB; Kurrasch-Orbaugh, D; Marona-Lewicka, D; Cumbay, MG; Watts, VJ; Barker, EL; Nichols, DE. Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines. J. Med. Chem., 1 Jan 2000, 43 (24), 4701–4710. 494 kB. doi:10.1021/jm000339w

5474
Analogue 4: Adding Methylthio at R6

6-MeS-DMT

IUPAC: N,N-Dimethyl-2-[6-(methylsulfanyl)-1H-indol-3-yl]ethan-1-amine

Formula: C13H18N2S Molecular weight: 234.36042 g/mol InChI Key: MPJJWNRFLZHFRQ-UHFFFAOYSA-N

InChI=1S/C13H18N2S/c1-15(2)7-6-10-9-14-13-8-11(16-3)4-5-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

PubChem CID: 44278537; ChemSpider: 23126489

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

Kline, TB; Benington, F; Morin, RD; Beaton, JM; Glennon, RA; Domelsmith, LN; Houk, KN; Rozeboom, MD. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives. J. Med. Chem., 1 Jan 1982, 25 (11), 1381–1383. 378 kB. doi:10.1021/jm00353a021

5487
Analogue 5: Adding Nitro at R6

IUPAC: N,N-Dimethyl-2-(6-nitro-1H-indol-3-yl)ethan-1-amine

Formula: C12H15N3O2 Molecular weight: 233.2664 g/mol InChI Key: NLAFXNOBKQIABX-UHFFFAOYSA-N

InChI=1S/C12H15N3O2/c1-14(2)6-5-9-8-13-12-7-10(15(16)17)3-4-11(9)12/h3-4,7-8,13H,5-6H2,1-2H3

PubChem CID: 4320738; ChemSpider: 3525666

Mckay, JB; Parkhursrt, RM; Silversteinax, M; Skinne, DWA. Analogues of psilocin and lysergic acid diethylamide. I. Chloro, nitro, and amino derivatives of 3-substituted indoles. Can. J. Chem., 1 Jan 1963, 41 (10), 2585–2590. 249 kB. doi:10.1139/v63-378

5493
Analogue 6: Adding Amino at R6

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-6-amine

Formula: C12H17N3 Molecular weight: 203.28348 g/mol InChI Key: VMKMTGSIPCKLSC-UHFFFAOYSA-N

InChI=1S/C12H17N3/c1-15(2)6-5-9-8-14-12-7-10(13)3-4-11(9)12/h3-4,7-8,14H,5-6,13H2,1-2H3

PubChem CID: 19040754

Mckay, JB; Parkhursrt, RM; Silversteinax, M; Skinne, DWA. Analogues of psilocin and lysergic acid diethylamide. I. Chloro, nitro, and amino derivatives of 3-substituted indoles. Can. J. Chem., 1 Jan 1963, 41 (10), 2585–2590. 249 kB. doi:10.1139/v63-378

5770
Analogue 7: Adding Methyl at R6

6-Me-DMT
N,N,6-TMT

IUPAC: N,N-Dimethyl-2-(6-methyl-1H-indol-3-yl)ethan-1-amine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: ODOKWPMMQYDQIA-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-10-4-5-12-11(6-7-15(2)3)9-14-13(12)8-10/h4-5,8-9,14H,6-7H2,1-3H3

5656
Analogue 8: Adding Chloro at R6

6-Chloro-DMT

IUPAC: 2-(6-Chloro-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15ClN2 Molecular weight: 222.7139 g/mol InChI Key: ISARSRVZSPZICH-UHFFFAOYSA-N

InChI=1S/C12H15ClN2/c1-15(2)6-5-9-8-14-12-7-10(13)3-4-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3

Benington, F; Morin, RD; Clark, LC. Synthesis of some 5- and 6-chloro, 5-methyl, and 5,6,7-trimethyl derivatives of tryptamine. J. Org. Chem., 1 Sep 1960, 25 (9), 1542–1547. 857 kB. doi:10.1021/jo01079a020

Six R7 analogues:
5155
Analogue 1: Adding Methoxy at R7

7-MeO-DMT
7-Methoxy-N,N-dimethyltryptamine

IUPAC: 2-(7-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: GCEZYLSUTMYNRN-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2)8-7-10-9-14-13-11(10)5-4-6-12(13)16-3/h4-6,9,14H,7-8H2,1-3H3

PubChem CID: 12017580; ChemSpider: 23183416

See also TiHKAL: #39 4-MeO-MIPT #40 5-MeO-MIPT

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

5208
Analogue 2: Adding Hydroxy at R7

7-HO-DMT

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-7-ol

Formula: C12H16N2O Molecular weight: 204.26824 g/mol InChI Key: FZFHBMMTKKWEQH-UHFFFAOYSA-N

InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-12-10(9)4-3-5-11(12)15/h3-5,8,13,15H,6-7H2,1-2H3

PubChem CID: 23757258

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

5222
Analogue 3: Adding Methyl at R7

N,N,7-TMT
N,N,7-Trimethyltryptamine

IUPAC: N,N-Dimethyl-2-(7-methyl-1H-indol-3-yl)ethan-1-amine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: PQSFTUCFMWBITK-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-10-5-4-6-12-11(7-8-15(2)3)9-14-13(10)12/h4-6,9,14H,7-8H2,1-3H3

PubChem CID: 47747; ChemSpider: 43445

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

5714
Analogue 4: Adding Bromo at R7

7-Br-DMT

IUPAC: 2-(7-Bromo-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15BrN2 Molecular weight: 267.1649 g/mol InChI Key: AIGRKPCJNQCZCI-UHFFFAOYSA-N

InChI=1S/C12H15BrN2/c1-15(2)7-6-9-8-14-12-10(9)4-3-5-11(12)13/h3-5,8,14H,6-7H2,1-2H3

PubChem CID: 12650285; ChemSpider: 23118496

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

5715
Analogue 5: Adding Ethyl at R7

7-Et-DMT

IUPAC: 2-(7-Ethyl-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C14H20N2 Molecular weight: 216.322 g/mol InChI Key: DNEWEHQANHHHCZ-UHFFFAOYSA-N

InChI=1S/C14H20N2/c1-4-11-6-5-7-13-12(8-9-16(2)3)10-15-14(11)13/h5-7,10,15H,4,8-9H2,1-3H3

PubChem CID: 12650284; ChemSpider: 23118849

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

5771
Analogue 6: Adding Bromo at R7

7-Br-DMT

IUPAC: 2-(7-Bromo-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15BrN2 Molecular weight: 267.1649 g/mol InChI Key: AIGRKPCJNQCZCI-UHFFFAOYSA-N

InChI=1S/C12H15BrN2/c1-15(2)7-6-9-8-14-12-10(9)4-3-5-11(12)13/h3-5,8,14H,6-7H2,1-2H3

13 skeleton analogues:
5052
Analogue 1: With Indol-3-ylethyl-cyclic-amine skeleton

pyr-T
Tryptamine, N,N-tetramethylene
Indole, 3-[2-(1-pyrrolidyl)ethyl]
Pyrrolidine, 1-[2-(3-indolyl)ethyl]
N,N-Tetramethylenetryptamine
1-[2-(1H-Indol-3-yl)ethyl]pyrrolidine
1-[2-(1-Pyrrolidyl)ethyl]indole
Pyrrolidyltryptamine

IUPAC: 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole

Formula: C14H18N2 Molecular weight: 214.30612 g/mol InChI Key: CVTZCBLFHNGYDQ-UHFFFAOYSA-N

InChI=1S/C14H18N2/c1-2-6-14-13(5-1)12(11-15-14)7-10-16-8-3-4-9-16/h1-2,5-6,11,15H,3-4,7-10H2

PubChem CID: 26393; ChemSpider: 24588; Drugs Forum: pyr-T; Wikipedia: Pyr-T

See also TiHKAL: #2 DBT
#24 4-HO-pyr-T
#29 5,6-MDO-DIPT
#43 5-MeO-pyr-T

See also Transcripts: 5.652

See also Chemistry notes VIII: p. 102, pyr-T: Synthesis
p. 103, pyr-T: Synthesis
p. 104, pyr-T: Synthesis
p. 112, pyr-T (α,β-keto): Synthesis

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

5189
Analogue 2: With Indol-3-ylethyl-cyclic-amine skeleton

pip-T
N,N-Pentamethylenetryptamine

IUPAC: 3-[2-(Piperidin-1-yl)ethyl]-1H-indole

Formula: C15H20N2 Molecular weight: 228.3327 g/mol InChI Key: PJVCNRSWJSLGCV-UHFFFAOYSA-N

InChI=1S/C15H20N2/c1-4-9-17(10-5-1)11-8-13-12-16-15-7-3-2-6-14(13)15/h2-3,6-7,12,16H,1,4-5,8-11H2

PubChem CID: 33560; ChemSpider: 30961

See also TiHKAL: #52 pyr-T  
See also Chemistry notes VIII: p. 110, pip-T: Synthesis

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

5190
Analogue 3: With Indol-3-ylethyl-cyclic-amine skeleton

mor-T
N,N-Ethyleneoxyethylenetryptamine

IUPAC: 3-[2-(Morpholin-4-yl)ethyl]-1H-indole

Formula: C14H18N2O Molecular weight: 230.30552 g/mol InChI Key: OITOJWZZJMQEAB-UHFFFAOYSA-N

InChI=1S/C14H18N2O/c1-2-4-14-13(3-1)12(11-15-14)5-6-16-7-9-17-10-8-16/h1-4,11,15H,5-10H2

PubChem CID: 213527; ChemSpider: 185133

See also TiHKAL: #52 pyr-T  
See also Chemistry notes VIII: p. 113, mor-T (α,β-keto): Synthesis
5069
Analogue 4: With 2-(1-Benzothiophen-3-yl)ethanamine skeleton

IUPAC: 2-(1-Benzothiophen-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15NS Molecular weight: 205.3192 g/mol InChI Key: QAPUMUJBYRYLGE-UHFFFAOYSA-N

InChI=1S/C12H15NS/c1-13(2)8-7-10-9-14-12-6-4-3-5-11(10)12/h3-6,9H,7-8H2,1-2H3

PubChem CID: 25118; ChemSpider: 23463

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

5070
Analogue 5: With 2-(1H-Inden-3-yl)ethanamine skeleton

C-DMT
3-(2-(Dimethylamino)ethyl)indene

IUPAC: 2-(1H-Inden-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H17N Molecular weight: 187.28078 g/mol InChI Key: FOBWFOXXVASKOU-UHFFFAOYSA-N

InChI=1S/C13H17N/c1-14(2)10-9-12-8-7-11-5-3-4-6-13(11)12/h3-6,8H,7,9-10H2,1-2H3

PubChem CID: 547452; ChemSpider: 476501

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

5073
Analogue 6: With 2-(1H-Indol-3-yl)cyclopropanamine skeleton

IUPAC: (1S,2R)-2-(1H-Indol-3-yl)cyclopropanamine

Formula: C11H12N2 Molecular weight: 172.22638 g/mol InChI Key: WMUNIKSCJKEXKG-SCZZXKLOSA-N

InChI=1S/C11H12N2/c12-10-5-8(10)9-6-13-11-4-2-1-3-7(9)11/h1-4,6,8,10,13H,5,12H2/t8-,10+/m1/s1

PubChem CID: 11819486; ChemSpider: 9994139

Vangveravong, S; Kanthasamy, A; Lucaites, VL; Nelson, DL; Nichols, DE. Synthesis and serotonin receptor affinities of a series of trans-2-(indol-3-yl)cyclopropylamine derivatives. J. Med. Chem., 1 Jan 1998, 41 (25), 4995–5001. 140 kB. doi:10.1021/jm980318q

Vangveravong, S; Nichols, DE. Stereoselective synthesis of trans-2-(indol-3-yl)cyclopropylamines: Rigid tryptamine analogues. J. Org. Chem., 1 Jan 1995, 60 (11), 3409–3413. 654 kB. doi:10.1021/jo00116a028

5074
Analogue 7: With 2-(1H-Indol-3-yl)cyclopropanamine skeleton

IUPAC: (1R,2S)-2-(1H-Indol-3-yl)cyclopropanamine

Formula: C11H12N2 Molecular weight: 172.22638 g/mol InChI Key: WMUNIKSCJKEXKG-WCBMZHEXSA-N

InChI=1S/C11H12N2/c12-10-5-8(10)9-6-13-11-4-2-1-3-7(9)11/h1-4,6,8,10,13H,5,12H2/t8-,10+/m0/s1

PubChem CID: 10103618; ChemSpider: 8279145

Vangveravong, S; Kanthasamy, A; Lucaites, VL; Nelson, DL; Nichols, DE. Synthesis and serotonin receptor affinities of a series of trans-2-(indol-3-yl)cyclopropylamine derivatives. J. Med. Chem., 1 Jan 1998, 41 (25), 4995–5001. 140 kB. doi:10.1021/jm980318q

Vangveravong, S; Nichols, DE. Stereoselective synthesis of trans-2-(indol-3-yl)cyclopropylamines: Rigid tryptamine analogues. J. Org. Chem., 1 Jan 1995, 60 (11), 3409–3413. 654 kB. doi:10.1021/jo00116a028

5092
Analogue 8: With Gramine skeleton

Gramine
N,N-Dimethyl-3-methanamine indole

IUPAC: 1-(1H-Indol-3-yl)methanamine

Formula: C9H10N2 Molecular weight: 146.1891 g/mol InChI Key: JXYGLMATGAAIBU-UHFFFAOYSA-N

InChI=1S/C9H10N2/c10-5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5,10H2

PubChem CID: 472107; ChemSpider: 414602

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3077 kB. doi:10.1007/BF02818560

5224
Analogue 9: With Homotryptamine skeleton

U-6056
DMHT
N,N-Dimethylhomotryptamine

IUPAC: 3-(1H-Indol-3-yl)-N,N-dimethylpropan-1-amine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: QHNWPRMHGXRBAO-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-15(2)9-5-6-11-10-14-13-8-4-3-7-12(11)13/h3-4,7-8,10,14H,5-6,9H2,1-2H3

PubChem CID: 52549; ChemSpider: 47499

5243
Analogue 10: With Indol-3-ylethyl-cyclic-amine skeleton

dmpyrrol-T

IUPAC: 3-[2-(2,5-Dimethyl-1H-pyrrol-1-yl)ethyl]-1H-indole

Formula: C16H18N2 Molecular weight: 238.32752 g/mol InChI Key: DVRSFBAQFCZILZ-UHFFFAOYSA-N

InChI=1S/C16H18N2/c1-12-7-8-13(2)18(12)10-9-14-11-17-16-6-4-3-5-15(14)16/h3-8,11,17H,9-10H2,1-2H3

PubChem CID: 774193; ChemSpider: 676771

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

5400
Analogue 11: With Indol-3-ylethyl-cyclic-amine skeleton

mepipaz-T

IUPAC: 3-[2-(4-Methylpiperazin-1-yl)ethyl]-1H-indole

Formula: C15H21N3 Molecular weight: 243.34734 g/mol InChI Key: WHRBBWJHEWDMJS-UHFFFAOYSA-N

InChI=1S/C15H21N3/c1-17-8-10-18(11-9-17)7-6-13-12-16-15-5-3-2-4-14(13)15/h2-5,12,16H,6-11H2,1H3

PubChem CID: 15557283

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

5740
Analogue 12: With Homotryptamine skeleton

N-Methylhomotryptamine

IUPAC: 3-(1H-Indol-3-yl)-N-methylpropan-1-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: NSHWYAHUTQARKB-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-13-8-4-5-10-9-14-12-7-3-2-6-11(10)12/h2-3,6-7,9,13-14H,4-5,8H2,1H3

PubChem CID: 21472501

Sinhababu, AK; Ghosh, AK; Borchardt, RT. Molecular mechanism of action of 5,6-dihydroxytryptamine. Synthesis and biological evaluation of 4-methyl-, 7-methyl- and 4,7-dimethyl-5,6-dihydroxytryptamines. J. Med. Chem., 1 Sep 1985, 28 (9), 1273–1279. 1001 kB. doi:10.1021/jm00147a027

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

5785
Analogue 13: With Homotryptamine skeleton

Homotryptamine

IUPAC: 3-(1H-Indol-3-yl)propan-1-amine

Formula: C11H14N2 Molecular weight: 174.24226 g/mol InChI Key: OOIAXMPVZJKJHK-UHFFFAOYSA-N

InChI=1S/C11H14N2/c12-7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7,12H2

Khalil, EM; Angelis, JD; Cole, PA. Indoleamine analogs as probes of the substrate selectivity and catalytic mechanism of serotonin N-acetyltransferase. J. Biol. Chem., 13 Nov 1998, 273 (46), 30321–30327. 247 kB. doi:10.1074/jbc.273.46.30321

10 isomers:
5007
Isomer 1

2,α-DMT
2-Me-α-MT
Alpha-2
Tryptamine, 2,α-dimethyl
Indole, 2-methyl-3-(2-amino)propane
2,α-Dimethyltryptamine
2-Methyl-3-(2-amino)propylindole

IUPAC: 1-(2-Methyl-1H-indol-3-yl)propan-2-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: AXZQFXRPULJFQK-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-8(13)7-11-9(2)14-12-6-4-3-5-10(11)12/h3-6,8,14H,7,13H2,1-2H3

PubChem CID: 44719453; ChemSpider: 23511903; Wikipedia: 2,alpha-DMT

5008
Isomer 2

α,N-DMT
Alpha-N
Tryptamine, α,N-dimethyl
Indole, 3-[2-(methylamino)propyl]
α,N-Dimethyltryptamine
3-[2-(Methylamino)propyl]indole

IUPAC: 1-(1H-Indol-3-yl)-N-methylpropan-2-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: HUWIYJREHSBOEO-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-9(13-2)7-10-8-14-12-6-4-3-5-11(10)12/h3-6,8-9,13-14H,7H2,1-2H3

PubChem CID: 3724428; ChemSpider: 2955156; Wikipedia: Alpha,N-DMT

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

Repke, DB; Ferguson, WJ; Bates, DK. Synthesis of secondary methylalkylamines. Tetrahedron Lett., 1979, 20 (43), 4183–4184. 149 kB. doi:10.1016/S0040-4039(01)86538-2

5011
Isomer 3

α-ET
AET
Monase
α-Ethyltryptamine
Indole, 3-(2-aminobutyl)
Tryptamine, α-ethyl
3-(2-Aminobutyl)indole

IUPAC: 1-(1H-Indol-3-yl)butan-2-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: ZXUMUPVQYAFTLF-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3

PubChem CID: 8367; ChemSpider: 8064; Erowid: AET; Wikipedia: Alpha-Ethyltryptamine

See also TiHKAL: #26 LSD #48 α-MT

Steiner, WG; Pscheidt, GR; Costa, E; Himwich, HE. α-Ethyltryptamine (etryptamine): An electroencephalographic, behavioral and neurochemical analysis. Psychopharmacology, 1 Sep 1963, 4 (5), 354–366. 780 kB. doi:10.1007/BF00405246

Daldrup, T; Heller, C; Matthiesen, U; Honus, S; Bresges, A; Haarhoff, K. Etryptamin, eine neue designer-droge mit fataler Wirkung. Z. Rechtsmed., 1 Sep 1986, 97 (1), 61–68. 496 kB. doi:10.1007/BF00200960

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Hong, S; Young, R; Glennon, RA. Discriminative stimulus properties of α-ethyltryptamine optical isomers. Pharmacol. Biochem. Behav., 1 Oct 2001, 70 (2–3),. 131 kB. doi:10.1016/S0091-3057(01)00605-0

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

Glennon, RA. MDMA-like stimulus effects of α-ethyltryptamine and the α-ethyl homolog of DOM. Pharmacol. Biochem. Behav., 1 Oct 1993, 46 (2), 459–462. 396 kB. doi:10.1016/0091-3057(93)90379-8

Huang, X; Johnson, MP; Nichols, DE. Reduction in brain serotonin markers by α-ethyltryptamine (Monase). Eur. J. Pharmacol., 1 Jan 1991, 200 (1), 187–190. 420 kB. doi:10.1016/0014-2999(91)90686-K

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Krebs, KM; Geyer, MA. Behavioral characterization of alpha-ethyltryptamine, a tryptamine derivative with MDMA-like properties in rats. Psychopharmacology, 1 Dec 1993, 113 (2), 284–287. 472 kB. doi:10.1007/BF02245712

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

Meyers-Riggs, B. Alpha substituted tryptamines. countyourculture: rational exploration of the underground, 1 Mar 2012.

5049
Isomer 4

NET
N-Ethyltryptamine
Tryptamine, N-ethyl
Indole, 3-[2-(ethylamino)ethyl]
3-[2-(Ethylamino)ethyl]indole

IUPAC: N-Ethyl-2-(1H-indol-3-yl)ethan-1-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: TZWUSTVNAVKAPA-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-2-13-8-7-10-9-14-12-6-4-3-5-11(10)12/h3-6,9,13-14H,2,7-8H2,1H3

PubChem CID: 6092; ChemSpider: 5867; Wikipedia: N-Ethyltryptamine

See also TiHKAL: #6 DMT
#9 DPT
#10 EIPT
#26 LSD
See also Chemistry notes VIII: p. 52, NET: Synthesis
p. 54, NET: Synthesis
p. 55, NET: GC-MS
p. 64, NET: Synthesis
p. 65, NET: GC-MS

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

5178
Isomer 5

1,α-DMT
α,1-Dimethyltryptamine

IUPAC: 1-(1-Methyl-1H-indol-3-yl)propan-2-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: JCKSLVLEMICSDG-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-9(13)7-10-8-14(2)12-6-4-3-5-11(10)12/h3-6,8-9H,7,13H2,1-2H3

PubChem CID: 3354567; ChemSpider: 2600799

See also TiHKAL: #48 α-MT  
5179
Isomer 6

α,α-DMT
α,α-Dimethyltryptamine

IUPAC: 1-(1H-Indol-3-yl)-2-methylpropan-2-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: WREHPEFXXFJIIJ-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-12(2,13)7-9-8-14-11-6-4-3-5-10(9)11/h3-6,8,14H,7,13H2,1-2H3

PubChem CID: 9353; ChemSpider: 8987

See also TiHKAL: #48 α-MT  
5180
Isomer 7

4,α-DMT
α,4-Dimethyltryptamine

IUPAC: 1-(4-Methyl-1H-indol-3-yl)propan-2-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: KEOYEGHPRBDSKD-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-8-4-3-5-11-12(8)10(7-14-11)6-9(2)13/h3-5,7,9,14H,6,13H2,1-2H3

PubChem CID: 53990585; ChemSpider: 25392939

See also TiHKAL: #48 α-MT  

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

5596
Isomer 8

7-Me-AMT
α,7-DMT

IUPAC: 1-(7-Methyl-1H-indol-3-yl)propan-2-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: ISJMGGZLKGIAFX-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-8-4-3-5-11-10(6-9(2)13)7-14-12(8)11/h3-5,7,9,14H,6,13H2,1-2H3

PubChem CID: 6486609; ChemSpider: 4987047

5740
Isomer 9

N-Methylhomotryptamine

IUPAC: 3-(1H-Indol-3-yl)-N-methylpropan-1-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: NSHWYAHUTQARKB-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-13-8-4-5-10-9-14-12-7-3-2-6-11(10)12/h2-3,6-7,9,13-14H,4-5,8H2,1H3

PubChem CID: 21472501

Sinhababu, AK; Ghosh, AK; Borchardt, RT. Molecular mechanism of action of 5,6-dihydroxytryptamine. Synthesis and biological evaluation of 4-methyl-, 7-methyl- and 4,7-dimethyl-5,6-dihydroxytryptamines. J. Med. Chem., 1 Sep 1985, 28 (9), 1273–1279. 1001 kB. doi:10.1021/jm00147a027

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

5748
Isomer 10

5-Ethyltryptamine

IUPAC: 2-(5-Ethyl-1H-indol-3-yl)ethan-1-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: HNICQKBUQQHUMM-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-2-9-3-4-12-11(7-9)10(5-6-13)8-14-12/h3-4,7-8,14H,2,5-6,13H2,1H3

PubChem CID: 188006; ChemSpider: 163417

Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. doi:10.1021/jm950498t

Show all 158 analogues and isomers Show only the 92 N analogues Show only the one N+ analogues Show only the one α analogues Show only the two R1 analogues Show only the one R2 analogues Show only the nine R4 analogues Show only the 15 R5 analogues Show only the eight R6 analogues Show only the six R7 analogues Show only the 13 skeleton analogues
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