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TiHKAL#50 NMT
5050
Variant: N α R2 R4 R5 R7 skeleton isomers all
Analogues: 92 2 1 3 12 1 10 4 125

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

92 N analogues:
5002
Analogue 1: Substituting Dibutyl for Methyl 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

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; 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

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

5003
Analogue 2: Substituting Diethyl for Methyl 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

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

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. 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.

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.

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.

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.

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

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; 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

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; 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

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

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

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

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

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

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

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

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

5004
Analogue 3: Substituting Diisopropyl for Methyl 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 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

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.

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.

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.

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

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

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

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

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

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

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

5006
Analogue 4: Substituting Dimethyl for Methyl at N

DMT
Tryptamine, N,N-dimethyl
Indole, 3-[2-(dimethylamino)ethyl]
N,N-Dimethyltryptamine
Desoxybufotenine
3-[2-(Dimethylamino)ethyl]indole
Nigerine

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 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

Fenderson5555. DMT from tryptophan? 23 Mar 2011.

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

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; 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

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

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

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

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

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; 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

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

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

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

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

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

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.

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.

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.

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.

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

Fenderson5555. Mechanisms in DMT synthesis. 3 Jan 2011.

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.

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

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.

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

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

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

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

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

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

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

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

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; 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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; 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

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

5009
Analogue 5: Substituting Dipropyl for Methyl 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 Chemistry notes VIII: p. 63, DPT: GC-MS
p. 83, DPT: Synthesis
p. 84, DPT: GC-MS
p. 85, DPT: 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.

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.

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

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

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

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.

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

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.

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

Toad. DPT Primer. Erowid, 15 Nov 1998.

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.

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

5010
Analogue 6: Substituting Ethyl and Isopropyl for Methyl 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 7: Substituting Butyl and Methyl for Methyl 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 8: Substituting Methyl and Isopropyl for Methyl 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 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

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

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

5049
Analogue 9: Substituting Ethyl for Methyl 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

5053
Analogue 10: Removing Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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

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; 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

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

5175
Analogue 17: Substituting Propyl and Methyl for Methyl 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 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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 Methyl 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

Two α analogues:
5008
Analogue 1: Adding Methyl at α

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

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

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

5788
Analogue 2: Adding Carboxy at α

Abrine

IUPAC: N-Methyltryptophan

Formula: C12H14N2O2 Molecular weight: 218.25176 g/mol InChI Key: CZCIKBSVHDNIDH-UHFFFAOYSA-N

InChI=1S/C12H14N2O2/c1-13-11(12(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,13-14H,6H2,1H3,(H,15,16)

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

One R2 analogue:
5107
Analogue 1: Adding Hydroxy at R2

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

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

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

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

See also TiHKAL: #6 DMT  
Three R4 analogues:
5123
Analogue 1: Adding Phosphoryloxy at R4

Baeocystin
N-Methyl-4-phosphoryloxytryptamine

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

Formula: C11H15N2O4P Molecular weight: 270.221561 g/mol InChI Key: WTPBXXCVZZZXKR-UHFFFAOYSA-N

InChI=1S/C11H15N2O4P/c1-12-6-5-8-7-13-9-3-2-4-10(11(8)9)17-18(14,15)16/h2-4,7,12-13H,5-6H2,1H3,(H2,14,15,16)

PubChem CID: 161359; ChemSpider: 141741; Wikipedia: Baeocystin

See also TiHKAL: #18 4-HO-DMT #39 4-MeO-MIPT

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

Leung, AY; Paul, AG. Baeocystin, a mono-methyl analog of psilocybin from Psilocybe baeocystis saprophytic culture. J. Pharm. Sci., 1 Jan 1966, 56 (1), 146. 101 kB. doi:10.1002/jps.2600560132

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

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

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

5125
Analogue 2: Adding Hydroxy at R4

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

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

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

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

PubChem CID: 14107683; ChemSpider: 27283888

See also TiHKAL: #18 4-HO-DMT  

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.

5064
Analogue 3: Adding Methoxy at R4

4-MeO-NMT
4-Methoxy-N-methyltryptamine

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

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

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

ChemSpider: 23511915

See also TiHKAL: #39 4-MeO-MIPT  
12 R5 analogues:
5042
Analogue 1: Adding Methoxy at R5

5-MeO-NMT
N,O-DMS
nor-5-MeO-DMT
Tryptamine, 5-methoxy-N-methyl
Indole, 5-methoxy-3-[2-(methylamino)ethyl]
Serotonin, N,O-dimethyl
5-Methoxy-N-methyltryptamine
5-Methoxy-3-[2-(methylamino)ethyl]indole
N,O-Dimethylserotonin

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N-methylethan-1-amine

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

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

PubChem CID: 16184; ChemSpider: 15360; Wikipedia: 5-MeO-NMT

See also TiHKAL: #6 DMT
#36 5-MeO-DET
#38 5-MeO-DMT
#40 5-MeO-MIPT

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

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. 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.

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5131
Analogue 2: Adding Hydroxy at R5

5-HO-NMT
Norbufotenine
N-Methylserotonin
5-Hydroxy-N-methyltryptamine

IUPAC: 3-[2-(Methylamino)ethyl]-1H-indol-5-ol

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

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

PubChem CID: 150885; ChemSpider: 132989

See also TiHKAL: #19 5-HO-DMT  

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

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

5860
Analogue 3: Adding Propoxy at R5

IUPAC: N-Methyl-2-(5-propoxy-1H-indol-3-yl)ethan-1-amine

Formula: C14H20N2O Molecular weight: 232.3214 g/mol InChI Key: PIBGHIUMDRKMBE-UHFFFAOYSA-N

InChI=1S/C14H20N2O/c1-3-8-17-12-4-5-14-13(9-12)11(10-16-14)6-7-15-2/h4-5,9-10,15-16H,3,6-8H2,1-2H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5891
Analogue 4: Adding Carbamoyl at R5

IUPAC: 3-[2-(Methylamino)ethyl]-1H-indole-5-carboxamide

Formula: C12H15N3O Molecular weight: 217.267 g/mol InChI Key: QYBFERHZVFESPF-UHFFFAOYSA-N

InChI=1S/C12H15N3O/c1-14-5-4-9-7-15-11-3-2-8(12(13)16)6-10(9)11/h2-3,6-7,14-15H,4-5H2,1H3,(H2,13,16)

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.

5867
Analogue 5: Adding Benzyloxy at R5

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

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

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

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5866
Analogue 6: Adding Cyclohexylmethoxy at R5

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

Formula: C18H26N2O Molecular weight: 286.41184 g/mol InChI Key: JNMBKQQISWSMJB-UHFFFAOYSA-N

InChI=1S/C18H26N2O/c1-19-10-9-15-12-20-18-8-7-16(11-17(15)18)21-13-14-5-3-2-4-6-14/h7-8,11-12,14,19-20H,2-6,9-10,13H2,1H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5865
Analogue 7: Adding Cyclopentylmethoxy at R5

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

Formula: C17H24N2O Molecular weight: 272.38526 g/mol InChI Key: DTZKERSVGSRHQC-UHFFFAOYSA-N

InChI=1S/C17H24N2O/c1-18-9-8-14-11-19-17-7-6-15(10-16(14)17)20-12-13-4-2-3-5-13/h6-7,10-11,13,18-19H,2-5,8-9,12H2,1H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5864
Analogue 8: Adding Cyclopentyloxy at R5

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

Formula: C16H22N2O Molecular weight: 258.35868 g/mol InChI Key: ZYTHRZPESCCSGK-UHFFFAOYSA-N

InChI=1S/C16H22N2O/c1-17-9-8-12-11-18-16-7-6-14(10-15(12)16)19-13-4-2-3-5-13/h6-7,10-11,13,17-18H,2-5,8-9H2,1H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5863
Analogue 9: Adding Hexyloxy at R5

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

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: YAUPVUHPFUVZMN-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-3-4-5-6-11-20-15-7-8-17-16(12-15)14(13-19-17)9-10-18-2/h7-8,12-13,18-19H,3-6,9-11H2,1-2H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5862
Analogue 10: Adding Pentyloxy at R5

IUPAC: N-Methyl-2-[5-(pentyloxy)-1H-indol-3-yl]ethan-1-amine

Formula: C16H24N2O Molecular weight: 260.37456 g/mol InChI Key: SYSKEKYINWMCEU-UHFFFAOYSA-N

InChI=1S/C16H24N2O/c1-3-4-5-10-19-14-6-7-16-15(11-14)13(12-18-16)8-9-17-2/h6-7,11-12,17-18H,3-5,8-10H2,1-2H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5861
Analogue 11: Adding Isopropoxy at R5

IUPAC: N-Methyl-2-[5-(propan-2-yloxy)-1H-indol-3-yl]ethan-1-amine

Formula: C14H20N2O Molecular weight: 232.3214 g/mol InChI Key: JWAWHXJWJPTCOF-UHFFFAOYSA-N

InChI=1S/C14H20N2O/c1-10(2)17-12-4-5-14-13(8-12)11(9-16-14)6-7-15-3/h4-5,8-10,15-16H,6-7H2,1-3H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5859
Analogue 12: Adding Ethoxy at R5

IUPAC: 2-(5-Ethoxy-1H-indol-3-yl)-N-methylethan-1-amine

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

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

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

One R7 analogue:
5160
Analogue 1: Adding Methoxy at R7

7-MeO-NMT
7-Methoxy-N-methyltryptamine

IUPAC: 2-(7-Methoxy-1H-indol-3-yl)-N-methylethan-1-amine

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

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

ChemSpider: 27993389

See also TiHKAL: #40 5-MeO-MIPT  
10 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 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
5073
Analogue 4: 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; 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

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

5074
Analogue 5: 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 6: 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

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

5243
Analogue 7: 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. 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.

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

5400
Analogue 8: 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 9: 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 10: 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

Four isomers:
5048
Isomer 1

α-MT
AMT
IT-290
3-IT
Tryptamine, α-methyl
Indole, 3-(2-aminopropyl)
α-Methyltryptamine
3-(2-Aminopropyl)indole

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

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

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

PubChem CID: 9287; ChemSpider: 8930; Drugs Forum: α-methyltryptamine; Erowid: AMT; Wikipedia: Alpha-Methyltryptamine

See also TiHKAL: #5 α,O-DMS
#7 2,α-DMT
#8 α,N-DMT
#11 α-ET
See also Pharmacology notes I: p. 135, α-MT

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

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

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

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

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

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.

Elliott, SP; Brandt, SD; Freeman, S; Archer, RP. AMT (3-(2-aminopropyl)indole) and 5-IT (5-(2-aminopropyl)indole): an analytical challenge and implications for forensic analysis. Drug Test. Anal., 1 Mar 2013, 5 (3), 196–202. 794 kB. doi:10.1002/dta.1420

Nichols, DE; Lloyd, DH; Johnson, MP; Hoffman, AJ. Synthesis and serotonin receptor affinities of a series of enantiomers of α-methyltryptamines: Evidence for the binding conformation of tryptamines at serotonin 5-HT1B receptors. J. Med. Chem., 1 Jan 1988, 31 (7), 1406–1412. 1085 kB. doi:10.1021/jm00402a026

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

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. Alpha substituted tryptamines. countyourculture: rational exploration of the underground, 1 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

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; 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

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; Chaurasia, C; Titeler, M. Binding of indolylalkylamines at 5-HT2 serotonin receptors: Examination of a hydrophobic binding region. J. Med. Chem., 1 Jan 1990, 33 (10), 2777–2784. 1248 kB. doi:10.1021/jm00172a016

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

5087
Isomer 2

5-Me-T
5-Methyltryptamine

IUPAC: 2-(5-Methyl-1H-indol-3-yl)ethan-1-amine

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

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

PubChem CID: 15760; ChemSpider: 14987

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

5090
Isomer 3

7-Me-T
7-Methyltryptamine

IUPAC: 2-(7-Methyl-1H-indol-3-yl)ethan-1-amine

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

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

PubChem CID: 26714; ChemSpider: 24888

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

5785
Isomer 4

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

Show all 125 analogues and isomers Show only the 92 N analogues Show only the two α analogues Show only the one R2 analogues Show only the three R4 analogues Show only the 12 R5 analogues Show only the one R7 analogues Show only the 10 skeleton analogues
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