Go to TiHKAL • info home
Browse the short index of TiHKAL tryptamines. Read book II of TiHKAL
Search for tryptamines and related structures Beyond TiHKAL—Selected writings by Sasha and others. Explore #49 NET
The alkaloids of the peyote cactus. Differences from the printed version
Go to PiHKAL • info home
Dear reader: PiHKAL • info, now well into its 2nd decade, is having a mid-life crisis. It has become surly, uncooperative and stubborn despite all my threats, shouting, and jumping about. Teenagers!

Right then, off to Bootstrap-camp with it! To shape up and become responsive! Still, this process of… iterative refinement may take some time. Thank you for your patience while PiHKAL • info unlearns what it has learned. · Comments or suggestions are always welcome.
You are currently exploring TiHKAL#49 NET.
To explore a different substance, type its name: Help
TiHKAL#49 NET
5049
Variant: N R5 skeleton isomers all
Analogues: 92 2 10 10 114

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: 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. http://dx.doi.org/10.1007/s00213-014-3557-7

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

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

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: 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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1039/b504001a

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

5003
Analogue 2: Substituting Diethyl for Ethyl at N

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

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: 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. http://dx.doi.org/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. http://dx.doi.org/10.1039/b504001a

Bõszõrményi, Z; Dér, P. Observations on the psychotogenic effect of N,N diethyltryptamine, a new tryptamine derivative. Br. J. Psychiatry, 1 Jan 1959, 105 (438), 171–181. 1388 kB. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1002/bmc.1657

5004
Analogue 3: Substituting Diisopropyl for Ethyl at N

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

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

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

See also Transcripts: 1.177

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

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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1039/b413014f

5006
Analogue 4: Substituting Dimethyl for Ethyl at N

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

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

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

See also Transcripts: 1.137, 3.327

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

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

Fenderson5555. DMT from tryptophan? 23 Mar 2011.

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

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

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

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

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

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

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

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

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

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

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

Pires, APS; Oliveira, CDR; Moura, S; Dõrr, 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. http://dx.doi.org/10.1002/pca.1110

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

5009
Analogue 5: Substituting Dipropyl for Ethyl at N

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

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

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

See also Transcripts: 4.462

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

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1039/b413014f

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

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

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

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

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

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. http://dx.doi.org/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. http://dx.doi.org/10.1016/j.neuropharm.2011.01.017

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

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

Toad. DPT Primer. Erowid, 15 Nov 1998.

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

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

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

5010
Analogue 6: Substituting Ethyl and Isopropyl for Ethyl at N

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

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: 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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1039/b413014f

5027
Analogue 7: Substituting Butyl and Methyl for Ethyl at N

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

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: 44719457; ChemSpider: 21106349; Wikipedia: Methylbutyltryptamine

See also TiHKAL: #36 5-MeO-DET  
5047
Analogue 8: Substituting Methyl and Isopropyl for Ethyl at N

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

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

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

See also Transcripts: 3.416

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

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

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

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

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1007/s00702-009-0308-8

5050
Analogue 9: Substituting Methyl for Ethyl at N

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

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: 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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1016/j.chroma.2009.10.088

5053
Analogue 10: Removing Ethyl at N

T
Indole, 3-(2-aminoethyl)
Tryptamine
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: 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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1124/mol.107.039255

5056
Analogue 11: Substituting Isopropyl for Ethyl at N

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

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: 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. http://dx.doi.org/10.1007/s00213-014-3557-7

5106
Analogue 12: Substituting Methyl and Hydroxy for Ethyl 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: 541950; ChemSpider: 471932

See also TiHKAL: #6 DMT  
5108
Analogue 13: Substituting Cyclopropyl for Ethyl 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: 41421; ChemSpider: 37794

See also TiHKAL: #6 DMT  
5121
Analogue 14: Substituting Isopropyl and Propyl for Ethyl 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: 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 Ethyl 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 Ethyl 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: 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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/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 Ethyl at N

MPT
N-Methyl-N-propyltryptamine

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

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

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

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

See also Transcripts: 4.460

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

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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1039/b504001a

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

5182
Analogue 18: Substituting Propyl for Ethyl 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: 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 Ethyl 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: 45582; ChemSpider: 41472

See also TiHKAL: #49 NET  
5184
Analogue 20: Substituting Isobutyl for Ethyl 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: 45586; ChemSpider: 41476

See also TiHKAL: #49 NET  
5185
Analogue 21: Substituting sec-Butyl for Ethyl 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: 24839509; ChemSpider: 23993854

See also TiHKAL: #49 NET  
5186
Analogue 22: Substituting tert-Butyl for Ethyl 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: 58980321; ChemSpider: 27128081

See also TiHKAL: #49 NET  
5187
Analogue 23: Substituting Pentyl for Ethyl 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: 23336456; ChemSpider: 15259292

See also TiHKAL: #49 NET  
5188
Analogue 24: Substituting Hexyl for Ethyl 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: 17843698; ChemSpider: 16002090

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

DALT
N,N-Diallyltryptamine
Indole, 3-[2-(Diallylamino)ethyl]
Tryptamine, N,N-Diallyl
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: 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. http://dx.doi.org/10.1002/jlcr.1557

5558
Analogue 26: Substituting 2-Ethoxybenzyl for Ethyl 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: 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. http://dx.doi.org/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 Ethyl 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. http://dx.doi.org/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 Ethyl 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: 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. http://dx.doi.org/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 Ethyl 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: 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. http://dx.doi.org/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 Ethyl 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: 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. http://dx.doi.org/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 Ethyl 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: 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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1039/b413014f

5075
Analogue 32: Substituting Ethyl and Propyl for Ethyl 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. http://dx.doi.org/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. http://dx.doi.org/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. http://dx.doi.org/10.1039/b413014f

5463
Analogue 33: Substituting Isobutyl and Methyl for Ethyl 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. http://dx.doi.org/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. http://dx.doi.org/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 Ethyl 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 Ethyl 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 Ethyl 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)

PubChem: 1712332; 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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-tert-Butoxy-2-oxoethyl for Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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: 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 Ethyl 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. http://dx.doi.org/10.1016/0028-3908(62)90015-1

5496
Analogue 91: Substituting Dihexyl for Ethyl 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. http://dx.doi.org/10.1016/0028-3908(62)90015-1

5743
Analogue 92: Substituting Hydroxy for Ethyl 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

PubChem: 56728; ChemSpider: 51154

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. http://dx.doi.org/10.1021/jm00325a020

Two R5 analogues:
429
Analogue 1: Adding Methoxy at R5

5-MeO-NET

IUPAC: N-Ethyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

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

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

PubChem: 23009084; ChemSpider: 12955759

See also Chemistry notes VIII: p. 101, 5-MeO-NET: 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. http://dx.doi.org/10.1007/s00213-014-3557-7

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. http://dx.doi.org/10.1021/jm00039a004

5892
Analogue 2: Adding Carbamoyl at R5

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

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

InChI=1S/C13H17N3O/c1-2-15-6-5-10-8-16-12-4-3-9(13(14)17)7-11(10)12/h3-4,7-8,15-16H,2,5-6H2,1H3,(H2,14,17)

Matzdorf, T. 5-Carboxamidotryptamin-derivate als liganden für 5-HT7- und 5-HT2A-rezeptoren: synthese und in-vitro-pharmakologie. Ph. D. Thesis, Universität Regensburg, Berlin, Germany, 23 Jan 2009. 1011 kB.

10 skeleton analogues:
5052
Analogue 1: With Indol-3-ylethyl-cyclic-amine skeleton

pyr-T
Pyrrolidyltryptamine
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

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: 26393; ChemSpider: 24588; Drugs Forum: pyr-T; Wikipedia: Pyr-T

See also TiHKAL: #2 DBT
#24 4-HO-pyr-T
#29 5,6-MDO-DIPT
#43 5-MeO-pyr-T

See also Transcripts: 5.652

See also Chemistry notes VIII: p. 102, pyr-T: Synthesis
p. 103, pyr-T: Synthesis
p. 104, pyr-T: Synthesis
p. 112, pyr-T (α,β-keto): Synthesis

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. http://dx.doi.org/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: 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. http://dx.doi.org/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: 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: 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. http://dx.doi.org/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. http://dx.doi.org/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: 10103618; ChemSpider: 8279145

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. http://dx.doi.org/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. http://dx.doi.org/10.1021/jm980318q

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: 472107; ChemSpider: 414602

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

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

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: 774193; ChemSpider: 676771

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

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

5400
Analogue 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: 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. http://dx.doi.org/10.1021/jm00190a014

5741
Analogue 9: With Homotryptamine skeleton

N-Ethylhomotryptamine

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

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

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

PubChem: 12297084; ChemSpider: 27286505

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. http://dx.doi.org/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. http://dx.doi.org/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

PubChem: 28989; ChemSpider: 26967

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. http://dx.doi.org/10.1074/jbc.273.46.30321

10 isomers:
5006
Isomer 1

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

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

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

See also Transcripts: 1.137, 3.327

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

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

Fenderson5555. DMT from tryptophan? 23 Mar 2011.

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

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

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

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

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

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

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

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

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

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

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

Pires, APS; Oliveira, CDR; Moura, S; Dõrr, 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. http://dx.doi.org/10.1002/pca.1110

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

5007
Isomer 2

2,α-DMT
2-Me-α-MT
Alpha-2
2-Methyl-3-(2-amino)propylindole
2,α-Dimethyltryptamine
Indole, 2-methyl-3-(2-amino)propane
Tryptamine, 2,α-dimethyl

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

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

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

PubChem: 44719453; ChemSpider: 23511903; Wikipedia: 2,alpha-DMT

5008
Isomer 3

α,N-DMT
Alpha-N
Tryptamine, α,N-dimethyl
3-[2-(Methylamino)propyl]indole
Indole, 3-[2-(methylamino)propyl]
α,N-Dimethyltryptamine

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: 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. http://dx.doi.org/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. http://dx.doi.org/10.1021/jm00321a017

5011
Isomer 4

α-ET
AET
Monase
3-(2-Aminobutyl)indole
Tryptamine, α-ethyl
Indole, 3-(2-aminobutyl)
α-Ethyltryptamine

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

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

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

PubChem: 8367; ChemSpider: 8064; Erowid: AET; Wikipedia: Alpha-Ethyltryptamine

See also TiHKAL: #26 LSD #48 α-MT

Steiner, WG; Pscheidt, GR; Costa, E; Himwich, HE. α-Ethyltryptamine (etryptamine): An electroencephalographic, behavioral and neurochemical analysis. Psychopharmacology, 1 Sep 1963, 4 (5), 354–366. 780 kB. http://dx.doi.org/10.1007/BF00405246

Daldrup, T; Heller, C; Matthiesen, U; Honus, S; Bresges, A; Haarhoff, K. Etryptamin, eine neue designer-droge mit fataler Wirkung. Z. Rechtsmed., 1 Sep 1986, 97 (1), 61–68. 496 kB. http://dx.doi.org/10.1007/BF00200960

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

Hong, S; Young, R; Glennon, RA. Discriminative stimulus properties of α-ethyltryptamine optical isomers. Pharmacol. Biochem. Behav., 1 Oct 2001, 70 (2–3),. 131 kB. http://dx.doi.org/10.1016/S0091-3057(01)00605-0

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

Glennon, RA. MDMA-like stimulus effects of α-ethyltryptamine and the α-ethyl homolog of DOM. Pharmacol. Biochem. Behav., 1 Oct 1993, 46 (2), 459–462. 396 kB. http://dx.doi.org/10.1016/0091-3057(93)90379-8

Huang, X; Johnson, MP; Nichols, DE. Reduction in brain serotonin markers by α-ethyltryptamine (Monase). Eur. J. Pharmacol., 1 Jan 1991, 200 (1), 187–190. 420 kB. http://dx.doi.org/10.1016/0014-2999(91)90686-K

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

Krebs, KM; Geyer, MA. Behavioral characterization of alpha-ethyltryptamine, a tryptamine derivative with MDMA-like properties in rats. Psychopharmacology, 1 Dec 1993, 113 (2), 284–287. 472 kB. http://dx.doi.org/10.1007/BF02245712

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

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

5178
Isomer 5

1,α-DMT
α,1-Dimethyltryptamine

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

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

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

PubChem: 3354567; ChemSpider: 2600799

See also TiHKAL: #48 α-MT  
5179
Isomer 6

α,α-DMT
α,α-Dimethyltryptamine

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

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

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

PubChem: 9353; ChemSpider: 8987

See also TiHKAL: #48 α-MT  
5180
Isomer 7

4,α-DMT
α,4-Dimethyltryptamine

IUPAC: 1-(4-Methyl-1H-indol-3-yl)propan-2-amine

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

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

PubChem: 53990585; ChemSpider: 25392939

See also TiHKAL: #48 α-MT  

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

5596
Isomer 8

7-Me-AMT
α,7-DMT

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

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

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

PubChem: 6486609; ChemSpider: 4987047

5740
Isomer 9

N-Methylhomotryptamine

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

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

InChI=1S/C12H16N2/c1-13-8-4-5-10-9-14-12-7-3-2-6-11(10)12/h2-3,6-7,9,13-14H,4-5,8H2,1H3

PubChem: 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. http://dx.doi.org/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. http://dx.doi.org/10.1021/jm00321a017

5748
Isomer 10

5-Ethyltryptamine

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

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

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

PubChem: 188006; ChemSpider: 163417

Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. http://dx.doi.org/10.1021/jm950498t

Show all 114 analogues and isomers Show only the 92 N analogues Show only the two R5 analogues Show only the 10 skeleton analogues
6 February 2016 · Creative Commons BY-NC-SA ·