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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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

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

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.

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

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

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

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

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

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

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.

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

Toad. DPT Primer. Erowid, 15 Nov 1998.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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

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

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

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.

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

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

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

IUPAC: 2-(1H-Indol-3-yl)ethanamine

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

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

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

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 &alpha-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

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

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

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

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

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

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.

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

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

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

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

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

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

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

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

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

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

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

PubChem CID: 45590; ChemSpider: 41480

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

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

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

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

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

PubChem CID: 541950; ChemSpider: 471932

NCPT
N-Cyclopropyltryptamine

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

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

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

PubChem CID: 41421; ChemSpider: 37794

PIPT
N-Isopropyl-N-propyltryptamine

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

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

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

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

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

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

MET
N-Ethyl-N-methyltryptamine

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

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

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

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

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

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

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

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

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

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

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

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

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

NPT
N-Propyltryptamine

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

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

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

PubChem CID: 45605; ChemSpider: 41495

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

NBT
N-Butyltryptamine

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

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

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

PubChem CID: 45582; ChemSpider: 41472

NIBT
N-Isobutyltryptamine

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

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

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

PubChem CID: 45586; ChemSpider: 41476

NSBT
N-sec-Butyltryptamine

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

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

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

PubChem CID: 24839509; ChemSpider: 23993854

NTBT
N-tert-Butyltryptamine

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

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

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

PubChem CID: 58980321; ChemSpider: 27128081

NAT
N-Pentyltryptamine

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

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

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

PubChem CID: 23336456; ChemSpider: 15259292

NHT
N-Hexyltryptamine

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

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

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

PubChem CID: 17843698; ChemSpider: 16002090

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

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

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

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

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

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

N-(2-Ethoxybenzyl)tryptamine

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

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

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

PubChem CID: 3162213; ChemSpider: 2413763

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.

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

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

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

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

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

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.

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

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

N-Benzyltryptamine

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

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

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

PubChem CID: 45592; ChemSpider: 41482

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.

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

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

N-(2-Hydroxybenzyl)tryptamine

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

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

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

PubChem CID: 2721617; ChemSpider: 2005549

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.

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

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

N-(2-Methoxybenzyl)tryptamine

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

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

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

PubChem CID: 1988048; ChemSpider: 1511014

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.

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

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

DIBT
N,N-Diisobutyltryptamine

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

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

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

PubChem CID: 45597; ChemSpider: 41487

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

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

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

EPT
N-Ethyl-N-propyltryptamine

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

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

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

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

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

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

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

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

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

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

N-Formyltryptamine

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

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

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

ChemSpider: 1361749

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

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

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

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

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

PubChem CID: 68541087

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

DMT N-oxide
DMT-NO

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

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

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

PubChem CID: 5316905; ChemSpider: 4475872

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

α,N,N-TMT
α,N,N-Trimethyltryptamine

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

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

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

Wikipedia: Alpha-N,N-Trimethyltryptamine

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

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

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

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

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

PubChem CID: 25927; ChemSpider: 24156

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

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

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

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

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

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

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

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

PubChem CID: 11138594; ChemSpider: 9313707

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Repke, DB; Ferguson, WJ; Bates, DK. Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols. J. Heterocycl. Chem., 1 Jan 1981, 18 (1), 175–179. 368 kB. doi:10.1002/jhet.5570180131

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Shulgin, AT. Profiles of psychedelic drugs. 8. Psilocybin. J. Psychedelic Drugs, 1 Jan 1980, 12 (1), 79. 822 kB. doi:10.1080/02791072.1980.10471557

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

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

PubChem CID: 21180; ChemSpider: 167880

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

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

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

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

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

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

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

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

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

4-Amino-DMT

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

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

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

PubChem CID: 57438418

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

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

4-F-DMT

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

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

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

PubChem CID: 11492162; ChemSpider: 9666968

Blair, JB. Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 1997. 3251 kB.

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

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

IUPAC: N,N-Dimethyl-2-(4-nitro-1H-indol-3-yl)ethanamine

Formula: C12H15N3O2 Molecular weight: 233.2664 g/mol InChI Key: ZDIYDYYEQOZCGA-UHFFFAOYSA-N

InChI=1S/C12H15N3O2/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)15(16)17/h3-5,8,13H,6-7H2,1-2H3

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

IUPAC: 2-(4-Chloro-1H-indol-3-yl)-N,N-dimethylethanamine

Formula: C12H15ClN2 Molecular weight: 222.7139 g/mol InChI Key: JLGAFYIPWQMGPG-UHFFFAOYSA-N

InChI=1S/C12H15ClN2/c1-15(2)7-6-9-8-14-11-5-3-4-10(13)12(9)11/h3-5,8,14H,6-7H2,1-2H3

PubChem CID: 23373080

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

5-HO-DMT
N,N-Dimethylserotonin
Bufotenine
Mappine
Tryptamine, N,N-dimethyl-5-hydroxy
Indol-5-ol, 3-[2-(dimethylamino)ethyl]
N,N-Dimethyl-5-hydroxytryptamine
3-(2-Dimethylaminoethyl)indol-5-ol

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

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

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

PubChem CID: 10257; ChemSpider: 9839; Erowid: Bufotenin; Wikipedia: Bufotenin

Ott, J. Pharmanopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine. J. Psychoactive Drugs, 1 Sep 2001, 33 (3), 273–281. 1122 kB. doi:10.1080/02791072.2001.10400574

Urban, JD; Clarke, WP; Zastrow, M; Nichols, DE; Kobilka, B; Weinstein, H; Javitch, JA; Roth, BL; Christopoulos, A; Sexton, PM; Miller, KJ; . Functional selectivity and classical concepts of quantitative pharmacology. J. Pharmacol. Exp. Ther., 1 Jan 2007, 320 (1), 1–13. 506 kB. doi:10.1124/jpet.106.104463

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

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

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

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

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

Shulgin, AT. Profiles of psychedelic drugs. 11. Bufotenine. J. Psychoactive Drugs, 1 Jan 1981, 13 (4), 389. 848 kB. doi:10.1080/02791072.1981.10471899

McBride, MC. Bufotenine: Toward an understanding of possible psychoactive mechanisms. J. Psychoactive Drugs, 1 Jan 2000, 32 (3), 321–331. 1591 kB. doi:10.1080/02791072.2000.10400456

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

Lyttle, T; Goldstein, D; Gartz, J. Bufo toads and bufotenine: Fact and fiction surrounding an alleged psychedelic. J. Psychoactive Drugs, 1 Sep 1996, 28 (3), 267–290. 24650 kB. doi:10.1080/02791072.1996.10472488

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

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

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

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

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

5-MeO-DMT
N,N,O-TMS
OMB
Tryptamine, 5-methoxy-N,N-dimethyl
Indole, 5-methoxy-3-[2-(dimethylamino)ethyl]
5-Methoxy-N,N-dimethyltryptamine
5-Methoxy-3-[2-(dimethylamino)ethyl]indole
N,N,O-Trimethylserotonin
Bufotenine methyl ether
O-Methylbufotenine

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine

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

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

PubChem CID: 1832; ChemSpider: 1766; Erowid: 5-MeO-DMT; Wikipedia: 5-MeO-DMT

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

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

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

Halberstadt, AL; Nichols, DE; Geyer, MA. Behavioral effects of α,α,β,β-tetradeutero-5-MeO-DMT in rats: comparison with 5-MeO-DMT administered in combination with a monoamine oxidase inhibitor. Psychopharmacology, 1 Jun 2012, 221 (4), 709–218. 296 kB. doi:10.1007/s00213-011-2616-6

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

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

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

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

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

Winter, JC; Filipink, RA; Timineri, D; Helsley, SE; Rabin, RA. The paradox of 5-methoxy-N,N-dimethyltryptamine: an indoleamine hallucinogen that induces stimulus control via 5-HT1A receptors. Pharmacol. Biochem. Behav., 1 Jan 2000, 65 (1), 75–82. 157 kB. doi:10.1016/S0091-3057(99)00178-1

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

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

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

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

Macor, JE; Fox, CB; Johnson, C; Koe, BK; Lebel, LA; Zorn, SH. 1-(2-Aminoethyl)-3-methyl-8,9-dihydropyrano[3,2-e]indole: A rotationally restricted phenolic analog of the neurotransmitter serotonin and agonist selective for serotonin (5-HT2-type) receptors. J. Med. Chem., 1 Jan 1992, 35 (20), 3625–3632. 1944 kB. doi:10.1021/jm00098a005

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

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

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

Glennon, RA; Titeler, M; Lyon, RA; Slusher, RM. N,N-Di-n-propylserotonin: Binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. J. Med. Chem., 1 Jan 1988, 31 (4), 867–870. 600 kB. doi:10.1021/jm00399a031

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

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

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

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

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

Callaway, JC; Grob, CS; McKenna, DJ; Nichols, DE; Shulgin, AT; Tupper, KW; Sklerov, JH; Levine, B; Moore, KA. A demand for clarity regarding a case report on the ingestion of 5-methoxy-N, N-Dimethyltryptamine (5-MeO-DMT) in an Ayahuasca preparation. J. Anal. Toxicol., 1 Jul 2006, 30 (6), 406–407. 53 kB. doi:10.1093/jat/30.6.406

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

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

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

5-MeS-DMT
Tryptamine, N,N-dimethyl-5-methylthio
Indole, 3-[2-(dimethylamino)ethyl]-5-methylthio
N,N-Dimethyl-5-methylthiotryptamine
3-[2-(Dimethylamino)ethyl]-5-methylthioindole

IUPAC: N,N-Dimethyl-2-[5-(methylsulfanyl)-1H-indol-3-yl]ethanamine

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

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

PubChem CID: 21180; ChemSpider: 19917; Wikipedia: 5-MeS-DMT

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

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

5-Br-DMT
5-Bromo-N,N-dimethyltryptamine

IUPAC: 2-(5-Bromo-1H-indol-3-yl)-N,N-dimethylethanamine

Formula: C12H15BrN2 Molecular weight: 267.1649 g/mol InChI Key: ATEYZYQLBQUZJE-UHFFFAOYSA-N

InChI=1S/C12H15BrN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3

PubChem CID: 360252; ChemSpider: 319812; Wikipedia: 5-Bromo-DMT

Morris, H; Wallach, J. Sea DMT: God Molecule or Barnacle Repellent?. Vice, 26 Mar 2013.

Bufoviridine
N,N-Dimethyl-5-sulfoxytryptamine

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl hydrogen sulfate

Formula: C12H16N2O4S Molecular weight: 284.33144 g/mol InChI Key: OYOOWLVMRZQOMJ-UHFFFAOYSA-N