Exploring TiHKAL#6 DMT. To explore a different substance, type its name:
TiHKAL#6 DMT
5006
Names: 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
Formula: C12H16N2 · Molecular weight: 188.26884
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

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

Fenderson5555. DMT from tryptophan? 23 Mar 2011.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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