Exploring DMT. To explore a different substance…

TiHKAL#6 DMT
Names:
DMT · Nigerine · Desoxybufotenine · Indole, 3-[2-(dimethylamino)ethyl] · Tryptamine, N,N-dimethyl · 3-[2-(Dimethylamino)ethyl]indole · N,N-Dimethyltryptamine
IUPAC name:
2-(1H-Indol-3-yl)-N,N-dimethylethan-1-amine
ID: 5006 · Formula: C12H16N2 · Molecular weight: 188.269
InChI: InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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

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.

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

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

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

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.

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

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

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

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

Fenderson5555. DMT from tryptophan? 23 Mar 2011.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Ciprian-Ollivier, J; Cetkovich-Bakmas, MG. Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr. Res., 19 Dec 1997, 28 (2–3), 257–265. 722 kB. http://dx.doi.org/10.1016/S0920-9964(97)00116-3

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

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

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

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

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

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

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

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

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

DBT
TiHKAL#2 DBT
DET
TiHKAL#3 DET
DIPT
TiHKAL#4 DIPT
DPT
TiHKAL#9 DPT
EIPT
TiHKAL#10 EIPT
MBT
TiHKAL#27 MBT
MIPT
TiHKAL#47 MIPT
NET
TiHKAL#49 NET
NMT
TiHKAL#50 NMT
T
TiHKAL#53 T
NIPT
TiHKAL#49 NIPT
N-HO-NMT
N-HO-NMT; N-Hydroxy-N-methyltryptamine
NCPT
NCPT; N-Cyclopropyltryptamine
PIPT
PIPT; N-Isopropyl-N-propyltryptamine
BIPT
BIPT; N-Butyl-N-isopropyltryptamine
MET
MET; N-Ethyl-N-methyltryptamine
MPT
MPT; N-Methyl-N-propyltryptamine
NPT
NPT; N-Propyltryptamine
NBT
NBT; N-Butyltryptamine
NIBT
NIBT; N-Isobutyltryptamine
NSBT
NSBT; N-sec-Butyltryptamine
NTBT
NTBT; N-tert-Butyltryptamine
NAT
NAT; N-Pentyltryptamine
NHT
NHT; N-[2-(1H-Indol-3-yl)ethyl]hexan-1-amine
DALT
TiHKAL#57 DALT
5558
N-(2-Ethoxybenzyl)tryptamine
5559
N-(2-Methoxyphenylethan-2-yl)tryptamine
N-Benzyltryptamine
N-Benzyltryptamine
5565
N-(2-Hydroxybenzyl)tryptamine
5566
N-(2-Methoxybenzyl)tryptamine
DIBT
DIBT; N,N-Diisobutyltryptamine
EPT
EPT; N-Ethyl-N-propyltryptamine
MIBT
MIBT; N-[2-(1H-Indol-3-yl)ethyl]-N,2-dimethylpropan-1-amine
MSBT
MSBT; N-[2-(1H-Indol-3-yl)ethyl]-N-methylbutan-2-amine
DSBT
DSBT; N-(Butan-2-yl)-N-[2-(1H-indol-3-yl)ethyl]butan-2-amine
N-Formyltryptamine
N-Formyltryptamine
5601
N-Benzyl-2-(1H-indol-3-yl)-N-methylethan-1-amine
5602
N-(4-Bromobenzyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine
5603
2-(1H-Indol-3-yl)-N-methyl-N-(2-phenylethyl)ethan-1-amine
5604
2-(1H-Indol-3-yl)-N-methyl-N-[2-(2-methylphenyl)ethyl]ethan-1-amine
5605
2-(2-Fluorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5606
2-(2-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5607
2-(2,5-Dimethylphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5608
2-(1H-Indol-3-yl)-N-[2-(2-methoxyphenyl)ethyl]-N-methylethan-1-amine
5609
2-(2,5-Dimethoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5610
2-(2,6-Dichlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5611
2-(1H-Indol-3-yl)-N-methyl-N-[2-(3-methylphenyl)ethyl]ethan-1-amine
5612
3-(2-{[2-(1H-Indol-3-yl)ethyl](methyl)amino}ethyl)phenyl acetate
5613
2-(1H-Indol-3-yl)-N-[2-(3-methoxyphenyl)ethyl]-N-methylethan-1-amine
5614
2-(3-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5615
2-(3-Bromophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5616
2-(3,5-Dimethylphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5617
2-(3,4-Dimethoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5618
2-(3,4-Dichlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5619
2-(1H-Indol-3-yl)-N-methyl-N-[2-(4-methylphenyl)ethyl]ethan-1-amine
5620
2-(1H-Indol-3-yl)-N-[2-(4-methoxyphenyl)ethyl]-N-methylethan-1-amine
5621
2-(4-Fluorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5622
2-(4-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5623
2-(4-Bromophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5624
2-(1H-Indol-3-yl)-N-methyl-N-[2-(4-nitrophenyl)ethyl]ethan-1-amine
5625
2-(Biphenyl-4-yl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5626
2-(1H-Indol-3-yl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5627
2-(1H-Indol-3-yl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5628
2-(1H-Indol-3-yl)-N-methyl-N-[2-(naphthalen-1-yl)ethyl]ethan-1-amine
5629
2-(1H-Indol-3-yl)-N-methyl-N-[2-(naphthalen-2-yl)ethyl]ethan-1-amine
5630
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-phenylpropan-1-amine
5631
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-(3,4,5-trimethoxyphenyl)propan-1-amine
5632
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-4-phenylbutan-1-amine
5633
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-(phenylsulfanyl)propan-1-amine
5634
N-[2-(1H-Indol-3-yl)ethyl]-N-methylpentan-1-amine
5635
N-[2-(1H-Indol-3-yl)ethyl]-N-methylhexan-1-amine
5636
N-[2-(1H-Indol-3-yl)ethyl]-N-methylheptan-1-amine
5637
N-[2-(1H-Indol-3-yl)ethyl]-N-methyloctan-1-amine
5638
N-[2-(1H-Indol-3-yl)ethyl]-N-methyldodecan-1-amine
5639
N-[2-(1H-Indol-3-yl)ethyl]-N-methyltetradecan-1-amine
5640
N-[2-(1H-Indol-3-yl)ethyl]-N-methyloctadecan-1-amine
5641
N-(Cyclopropylmethyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine
5642
N-(Cyclopentylmethyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine
5643
N-(Cyclohexylmethyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine
5645
2-Ethyl-N-[2-(1H-indol-3-yl)ethyl]-N-methylbutan-1-amine
5646
N-[2-(1H-Indol-3-yl)ethyl]-N-methylprop-2-en-1-amine
5647
N-[2-(1H-Indol-3-yl)ethyl]-N-methylprop-2-yn-1-amine
5648
3-Cyclohexyl-N-[2-(1H-indol-3-yl)ethyl]-N-methylpropan-1-amine
5649
(2E)-N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-phenylprop-2-en-1-amine
5650
Methyl N-[2-(1H-indol-3-yl)ethyl]-N-methylglycinate
5651
tert-Butyl N-[2-(1H-indol-3-yl)ethyl]-N-methylglycinate
5652
N2-[2-(1H-Indol-3-yl)ethyl]-N2-methylglycinamide
5653
3-{[2-(1H-Indol-3-yl)ethyl](methyl)amino}propanenitrile
5654
2-{[2-(1H-Indol-3-yl)ethyl](methyl)amino}ethyl acetate
DAT
DAT; N-[2-(1H-Indol-3-yl)ethyl]-N-pentylpentan-1-amine
DHT
DHT; N-Hexyl-N-[2-(1H-indol-3-yl)ethyl]hexan-1-amine
HOT-T
HOT-T; N-Hydroxy-1-(1H-indol-3-yl)propan-2-amine
DMT N-oxide
DMT N-oxide; [2-(1H-Indol-3-yl)ethyl]dimethylamine oxide
α,N,N-TMT
α,N,N-TMT; α,N,N-Trimethyltryptamine
1-Me-DMT
1-Me-DMT; N,N,1-Trimethyltryptamine
1-MeO-DMT · Lespedamine
1-MeO-DMT; Lespedamine
2-Me-DMT
TiHKAL#34 2-Me-DMT
4-HO-DMT · Psilocin
TiHKAL#18 4-HO-DMT
4-H2PO4-DMT · Psilocybin
TiHKAL#18 4-H2PO4-DMT
4-MeO-DMT
4-MeO-DMT; 4-Methoxy-N,N-dimethyltryptamine
4-MeS-DMT
4-MeS-DMT; N,N-Dimethyl-4-methylthiotryptamine
4-AcO-DMT
4-AcO-DMT; Psilacetin
4-Amino-DMT
4-Amino-DMT; 3-[2-(Dimethylamino)ethyl]-1H-indol-4-amine
4-F-DMT
4-F-DMT; 2-(4-Fluoro-1H-indol-3-yl)-N,N-dimethylethan-1-amine
5483
2-(4-Chloro-1H-indol-3-yl)-N,N-dimethylethan-1-amine
5484
N,N-Dimethyl-2-(4-nitro-1H-indol-3-yl)ethan-1-amine
5-HO-DMT
TiHKAL#19 5-HO-DMT
5-MeO-DMT
TiHKAL#38 5-MeO-DMT
5-MeS-DMT
TiHKAL#46 5-MeS-DMT
5-Br-DMT
5-Br-DMT; 5-Bromo-N,N-dimethyltryptamine
Bufoviridine
Bufoviridine
5-EtO-DMT
5-EtO-DMT; 5-Ethoxy-N,N-dimethyltryptamine
5-AcO-DMT
5-AcO-DMT; 5-Acetoxy-N,N-dimethyltryptamine
5,N,N-TMT
5,N,N-TMT; 5,N,N-Trimethyltryptamine
Sumatriptan
Sumatriptan
5-F-DMT
5-F-DMT; 2-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylethan-1-amine
5-Et-DMT
5-Et-DMT; 2-(5-Ethyl-1H-indol-3-yl)-N,N-dimethylethan-1-amine
5-Chloro-DMT
5-Chloro-DMT; 2-(5-Chloro-1H-indol-3-yl)-N,N-dimethylethan-1-amine
5-TMS-DMT
5-TMS-DMT; N,N-Dimethyl-2-[5-(trimethylsilyl)-1H-indol-3-yl]ethan-1-amine
5-Ac-DMT
5-Ac-DMT; 1-{3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}ethanone
5-Cam-DMT
5-Cam-DMT; 3-[2-(Dimethylamino)ethyl]-1H-indole-5-carboxamide
6-HO-DMT
6-HO-DMT; 6-Hydroxy-N,N-dimethyltryptamine
6-MeO-DMT
6-MeO-DMT; 6-Methoxy-N,N-dimethyltryptamine
6-F-DMT
6-F-DMT; 2-(6-Fluoro-1H-indol-3-yl)-N,N-dimethylethan-1-amine
6-MeS-DMT
6-MeS-DMT; N,N-Dimethyl-2-[6-(methylsulfanyl)-1H-indol-3-yl]ethan-1-amine
5487
N,N-Dimethyl-2-(6-nitro-1H-indol-3-yl)ethan-1-amine
5493
3-[2-(Dimethylamino)ethyl]-1H-indol-6-amine
6-Me-DMT
6-Me-DMT; N,N-Dimethyl-2-(6-methyl-1H-indol-3-yl)ethan-1-amine
6-Chloro-DMT
6-Chloro-DMT; 2-(6-Chloro-1H-indol-3-yl)-N,N-dimethylethan-1-amine
7-MeO-DMT
7-MeO-DMT; 7-Methoxy-N,N-dimethyltryptamine
7-HO-DMT
7-HO-DMT; 3-[2-(Dimethylamino)ethyl]-1H-indol-7-ol
N,N,7-TMT
N,N,7-TMT; N,N,7-Trimethyltryptamine
7-Br-DMT
7-Br-DMT; 2-(7-Bromo-1H-indol-3-yl)-N,N-dimethylethan-1-amine
7-Et-DMT
7-Et-DMT; 2-(7-Ethyl-1H-indol-3-yl)-N,N-dimethylethan-1-amine
7-Br-DMT
7-Br-DMT; 2-(7-Bromo-1H-indol-3-yl)-N,N-dimethylethan-1-amine
pyr-T
TiHKAL#52 pyr-T
pip-T
pip-T; N,N-Pentamethylenetryptamine
mor-T
mor-T; 3-[2-(Morpholin-4-yl)ethyl]-1H-indole
5069
2-(1-Benzothiophen-3-yl)-N,N-dimethylethan-1-amine
C-DMT
C-DMT; 2-(1H-Inden-3-yl)-N,N-dimethylethan-1-amine
5073
(1S,2R)-2-(1H-Indol-3-yl)cyclopropanamine
5074
(1R,2S)-2-(1H-Indol-3-yl)cyclopropanamine
Gramine
Gramine
U-6056 · DMHT
U-6056; N,N-Dimethylhomotryptamine
dmpyrrol-T
dmpyrrol-T; 3-[2-(2,5-Dimethyl-1H-pyrrol-1-yl)ethyl]-1H-indole
mepipaz-T
mepipaz-T; 3-[2-(4-Methylpiperazin-1-yl)ethyl]-1H-indole
N-Methylhomotryptamine
N-Methylhomotryptamine
Homotryptamine
Homotryptamine
2,α-DMT
TiHKAL#7 2,ɑ-DMT
α,N-DMT
TiHKAL#8 ɑ,N-DMT
α-ET
TiHKAL#11 ɑ-ET
NET
TiHKAL#49 NET
1,α-DMT
1,α-DMT; α,1-Dimethyltryptamine
α,α-DMT
α,α-DMT; α,α-Dimethyltryptamine
4,α-DMT
4,α-DMT; α,4-Dimethyltryptamine
7-Me-AMT
7-Me-AMT; 1-(7-Methyl-1H-indol-3-yl)propan-2-amine
N-Methylhomotryptamine
N-Methylhomotryptamine
5-Ethyltryptamine
5-Ethyltryptamine
DBT
TiHKAL#2 DBT
DET
TiHKAL#3 DET
DIPT
TiHKAL#4 DIPT
DPT
TiHKAL#9 DPT
EIPT
TiHKAL#10 EIPT
MBT
TiHKAL#27 MBT
MIPT
TiHKAL#47 MIPT
NET
TiHKAL#49 NET
NMT
TiHKAL#50 NMT
T
TiHKAL#53 T
NIPT
TiHKAL#49 NIPT
N-HO-NMT
N-HO-NMT; N-Hydroxy-N-methyltryptamine
NCPT
NCPT; N-Cyclopropyltryptamine
PIPT
PIPT; N-Isopropyl-N-propyltryptamine
BIPT
BIPT; N-Butyl-N-isopropyltryptamine
MET
MET; N-Ethyl-N-methyltryptamine
MPT
MPT; N-Methyl-N-propyltryptamine
NPT
NPT; N-Propyltryptamine
NBT
NBT; N-Butyltryptamine
NIBT
NIBT; N-Isobutyltryptamine
NSBT
NSBT; N-sec-Butyltryptamine
NTBT
NTBT; N-tert-Butyltryptamine
NAT
NAT; N-Pentyltryptamine
NHT
NHT; N-[2-(1H-Indol-3-yl)ethyl]hexan-1-amine
DALT
TiHKAL#57 DALT
5558
N-(2-Ethoxybenzyl)tryptamine
5559
N-(2-Methoxyphenylethan-2-yl)tryptamine
N-Benzyltryptamine
N-Benzyltryptamine
5565
N-(2-Hydroxybenzyl)tryptamine
5566
N-(2-Methoxybenzyl)tryptamine
DIBT
DIBT; N,N-Diisobutyltryptamine
EPT
EPT; N-Ethyl-N-propyltryptamine
MIBT
MIBT; N-[2-(1H-Indol-3-yl)ethyl]-N,2-dimethylpropan-1-amine
MSBT
MSBT; N-[2-(1H-Indol-3-yl)ethyl]-N-methylbutan-2-amine
DSBT
DSBT; N-(Butan-2-yl)-N-[2-(1H-indol-3-yl)ethyl]butan-2-amine
N-Formyltryptamine
N-Formyltryptamine
5601
N-Benzyl-2-(1H-indol-3-yl)-N-methylethan-1-amine
5602
N-(4-Bromobenzyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine
5603