5-HO-DMT
Bufotenine
Mappine
N,N-Dimethylserotonin
N,N-Dimethyl-5-hydroxytryptamine
Indol-5-ol, 3-[2-(dimethylamino)ethyl]
Tryptamine, N,N-dimethyl-5-hydroxy
3-(2-Dimethylaminoethyl)indol-5-ol
 
3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol
 5019 ·  C12H16N2O ·  204.268
 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
 VTTONGPRPXSUTJ-UHFFFAOYSA-N This stereoisomer Any stereoisomer
 CN(CCc1c[nH]c2c1cc(O)cc2)C

Ott, J. Pharmanopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine. J. Psychoactive Drugs, 1 Sep 2001, 33 (3), 273–281. 1.2 MB. https://doi.org/10.1080/02791072.2001.10400574

Urban, JD; Clarke, WP; von 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. https://doi.org/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. https://doi.org/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. 3.1 MB. https://doi.org/10.1007/BF02818560

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. https://doi.org/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. https://doi.org/10.1016/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. https://doi.org/10.1021/jm00190a014

Shulgin, AT. Profiles of psychedelic drugs. 11. Bufotenine. J. Psychoactive Drugs, 1 Jan 1981, 13 (4), 389. 848 kB. https://doi.org/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. 1.6 MB. https://doi.org/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. Analysis, 1 Jul 2012, 4 (7-8), 617-635. 270 kB. https://doi.org/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. 24.6 MB. https://doi.org/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. 9.5 MB. https://doi.org/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. https://doi.org/10.1016/0028-3908(90)90001-8

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. https://doi.org/10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

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. https://doi.org/10.1016/j.chroma.2009.10.088

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. https://doi.org/10.1021/jm00134a016

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. 1.0 MB. https://doi.org/10.1002/bmc.1551

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

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 1 Dec 2013, 27 (12), 1690-1700. 929 kB. https://doi.org/10.1002/bmc.2981

Blackledge, RD; Phelan, CP. Identification of bufotenine in Yopo seeds via GC/IRD. Microgram J., 1 Jan 2006, 4 (1–4), 3–11. 334 kB.

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 1 Oct 2014, 231 (21), 4135-4144. 298 kB. https://doi.org/10.1007/s00213-014-3557-7

Meyer, MR; Caspar, A; Brandt, SD; Maurer, HH. A qualitative/quantitative approach for the detection of 37 tryptamine-derived designer drugs, 5 β-carbolines, ibogaine, and yohimbine in human urine and plasma using standard urine screening and multi-analyte approaches. Anal. Bioanal. Chem., 1 Jan 2014, 406 (1), 225–237. 457 kB. https://doi.org/10.1007/s00216-013-7425-9

Brandt, SD; Martins, CPB. Analytical methods for psychoactive N,N-dialkylated tryptamines. Trends Anal. Chem., 1 Sep 2010, 29 (8), 858–869. 446 kB. https://doi.org/10.1016/j.trac.2010.04.008 #23

Baker, LE. Hallucinogens in drug discrimination. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 201-219. 342 kB. https://doi.org/10.1007/7854_2017_476

Collins, M. Some new psychoactive substances: Precursor chemical and synthesis-driver end-products. Drug Test. Analysis, 1 Jul 2001, 3 (7–8), 404–416. 178 kB. https://doi.org/10.1002/dta.315

Clarke, EGC. The identification of some proscribed psychedelic drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 46-50. 336 kB. https://doi.org/10.1016/S0015-7368(67)70370-9

McKenna, D; Riba, J. New world tryptamine hallucinogens and the neuroscience of ayahuasca. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2016; pp 283-311. 749 kB. https://doi.org/10.1007/7854_2016_472

Martin, R. Nachweis und Bestimmung halluzinogener Wirkstoffe und ihrer Metaboliten in Körperflüssigkeiten und Haaren. Toxichem Krimtech, 1 Jan 2015, 82 (2), 123–127. 448 kB.

May, JA; Chen, H; Rusinko, A; Lynch, VM; Sharif, NA; McLaughlin, MA. A novel and selective 5-HT2 receptor agonist with ocular hypotensive activity: (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole. J. Med. Chem., 2003, 46 (19), 4188–2195. 126 kB. https://doi.org/10.1021/jm030205t #1b

Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 2003; pp 67–137. 6.3 MB.

Jacob, P; Shulgin, AT. Structure-activity relationships of the classic hallucinogens and their analogs. In Hallucinogens: An update. NIDA Research Monograph 146; Lin, GC; Glennon, RA, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1994; pp 74–91. 51 kB.

Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., Wiley & Co., 1981; pp 1109–1137. 4.7 MB. #12

Shulgin, AT. Psychotomimetic agents. In Psychopharmacological Agents; Gordon, M, Ed., Academic Press, New York, 1976; Vol. 4, pp 59–146. 3.1 MB. #XVIII

Dean, JG. Indolethylamine-N-methyltransferase polymorphisms: Genetic and biochemical approaches for study of endogenous N,N-dimethyltryptamine. Front. Neurosci., 23 Apr 2018, 12 n/a. 2.1 MB. https://doi.org/10.3389/fnins.2018.00232 #5-HO-DMT

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77 (4), 1245–1272. 1.2 MB. https://doi.org/10.1016/j.talanta.2008.07.062 #Bufotenin

EMCDDA. New drugs in Europe, 2007, European Monitoring Centre for Drugs and Drug Addiction, 1 May 2008. 381 kB. #14

Hoffer, A; Osmond, H. The Hallucinogens, Academic Press, New York, 1967. 3.9 MB. #Bufotenine

Barry, TL; Petzinger, G; Zito, SW. GC/MS comparison of the West Indian aphrodisiac “Love Stone” to the Chinese medication “Chan Su”: Bufotenine and related bufadienolides. J. Forensic Sci., 1 Nov 1996, 41 (6), 1068–1073. 411 kB. https://doi.org/10.1520/JFS14052J #Bufotenine MS

5-MeO-α-MT
4-HO-DMT · Psilocin
5-MeO-NMT
6-HO-DMT
7-MeO-NMT
4-MeO-NMT
7-HO-DMT
DMT N-oxide
5246
4-HO-iso-DMT
4-MeO-α-MT
6-MeO-α-MT
5-EtO-T
1495
5-MeO-2-Me-T · 2,O-DMS
N,N,4-Trimethylaminorex
10852
4-Isopropylaminorex
5-MeO-7-Me-T
5-MeO-1-Me-T
4-MBOP
3-MBOP
2-MBOP
BNZMP
Nebracetam
13 November 2018 · Creative Commons BY-NC-SA ·