Explore α-Methyltryptamine

TiHKAL book II entry α-MT

ChemSpider 8930
PubChem 9287
Wikidata Q421163
Erowid AMT
Wikipedia alpha-Methyltryptamine
Blotter α-MT
PsychonautWiki AMT
Project Response AMT (1816-17)
bluelight.org The Big & Dandy AMT Thread Part 5
bluelight.org The Big & Dandy AMT Thread Part 4
bluelight.org The Big & Dandy AMT Thread Part 3
bluelight.org The Big & Dandy AMT Thread Part 2
bluelight.org The Big & Dandy AMT Thread Part 1
Rhodium Shulgin & Nichols: Three new psychotomimetics: para-DOT - MDMA - α,O-DMS
Rhodium Psychedelic chemistry by M. V. Smith, chapter 3
bluelight.org AMT Effects and Ratings Survey Results

TiHKAL #5 α,O-DMS · #7 2,α-DMT · #8 α,N-DMT · #11 α-ET

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. 1.1 MB. https://doi.org/10.1016/0028-3908(62)90015-1 #α-MT

Meyers-Riggs, B. Alpha substituted tryptamines. countyourculture, countyourculture: rational exploration of the underground, 1 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. https://doi.org/10.1016/j.talanta.2007.06.012

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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. https://doi.org/10.1016/0006-2952(83)90281-2 #α-MeT

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine_1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. https://doi.org/10.1016/0024-3205(91)90582-V

Glennon, RA; Chaurasia, C; Titeler, M. Binding of indolylalkylamines at 5-HT₂ serotonin receptors: Examination of a hydrophobic binding region. J. Med. Chem., 1 Jan 1990, 33 (10), 2777–2784. 1.2 MB. https://doi.org/10.1021/jm00172a016

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 #13

Nichols, DE; Lloyd, DH; Johnson, MP; Hoffman, AJ. Synthesis and serotonin receptor affinities of a series of enantiomers of α-methyltryptamines: Evidence for the binding conformation of tryptamines at serotonin 5-HT_1B receptors. J. Med. Chem., 1 Jul 1988, 31 (7), 1406–1412. 1.1 MB. https://doi.org/10.1021/jm00402a026 #1a NMR

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

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. https://doi.org/10.1021/jm00321a017 #1,2,3

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., 1 Jan 1986, 5 (4), 153–157. 577 kB. https://doi.org/10.1002/qsar.19860050404 #12,13

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT_2A 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

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 1 Jan 2008, 54 (1), 89–96. 1.9 MB. https://doi.org/10.1248/jhs.54.89

Khalil, EM; De Angelis, J; 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. https://doi.org/10.1074/jbc.273.46.30321

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. 1.6 MB.

Elliott, SP; Brandt, SD; Freeman, S; Archer, RP. AMT (3-(2-aminopropyl)indole) and 5-IT (5-(2-aminopropyl)indole): an analytical challenge and implications for forensic analysis. Drug Test. Anal., 1 Mar 2013, 5 (3), 196–202. 794 kB. https://doi.org/10.1002/dta.1420

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

Haig, SD; Kelly, C; Morden, C. A report of an outbreak of toxicity from a novel drug of abuse: ERIC-3. Emerg. Med. J., 1 Jul 2013, 30 (7), 543–545. 90 kB. https://doi.org/10.1136/emermed-2012-201631

Arunotayanun, W; Dalley, JW; Huang, X; Setola, V; Treble, R; Iversen, L; Roth, BL; Gibbons, S. An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: Emerging ‘novel psychoactive drugs’. Bioorg. Med. Chem. Lett., 1 Jun 2013, 23 (11), 3411-3415. 1.1 MB. https://doi.org/10.1016/j.bmcl.2013.03.066 #17

Dinger, J; Woods, C; Brandt, SD; Meyer, MR; Maurer, HH. Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class. Toxicol. Lett., 1 Jan 2016, 241, 82-94. 2.6 MB. https://doi.org/10.1016/j.toxlet.2015.11.013

Wagmann, L; Brandt, SD; Kavanagh, PV; Maurer, HH; Meyer, MR. In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks. Toxicol. Lett., 17 Apr 2017, 272, 84–93. 1.9 MB. https://doi.org/10.1016/j.toxlet.2017.03.007

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 #15

Chapman, SJ. PeakAL: Protons I Have Known and Loved, Too — Another Fifty Shades of Grey-Market Spectra. BLOTTER, 1 Mar 2018, 3 (1). 1.2 MB. https://doi.org/10.16889/isomerdesign-5

Chapman, SJ. PeakAL: Protons I Have Known and Loved, Too — Another Fifty Shades of Grey-Market Spectra. Supplementary Data. BLOTTER, 1 Mar 2018, 3 (1). 5.7 MB. https://doi.org/10.16889/isomerdesign-5-supp

Jones, LE; Stewart, A; Peters, KL; McNaul, M; Speers, SJ; Fletcher, NC; Bell, SEJ. Infrared and Raman screening of seized novel psychoactive substances: a large scale study of >200 samples. Analyst, 25 Jan 2016, 141 (3), 902–909. 1.3 MB. https://doi.org/10.1039/c5an02326b

Zhang, S; Fan, Y; Shi, Z; Cheng, S. DFT-based QSAR and action mechanism of phenylalkylamine and tryptamine hallucinogens. Chin. J. Chem., 1 Apr 2011, 29 (4), 623–630. 166 kB. https://doi.org/10.1002/cjoc.201190132 #56

Nichols, DE. Chemistry and structure–activity relationships of psychedelics. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 1-43. 2.6 MB. https://doi.org/10.1007/7854_2017_475 #19

Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 879 kB. https://doi.org/10.1007/7854_2016_466

Burns, L; Roxburgh, A; Bruno, R; Van Buskirk, J. Monitoring drug markets in the Internet age and the evolution of drug monitoring systems in Australia. Drug Test. Anal., 1 Jul 2014, 6 (7-8), 840-845. 113 kB. https://doi.org/10.1002/dta.1613

Nichols, DE. Structure-activity relationships of serotonin 5-HT_2A agonists. WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. https://doi.org/10.1002/wmts.42 #13

Wang, Y; Chen, C. Synthesis of deuterium labeled tryptamine derivatives. J. Chin. Chem. Soc., 1 Oct 2007, 54 (5), 1363-1368. 92 kB. https://doi.org/10.1002/jccs.200700194 #11

Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 24 Apr 2003; pp 67–137. 6.3 MB.

Shulgin, AT. Chemistry of psychotomimetics. In Handbook of Experimental Pharmacology. Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs; Hoffmeister, F; Stille, G, Eds., Springer-Verlag, Berlin, 1 Jan 1982; Vol. 55 (3), pp 3–29. 928 kB. https://doi.org/10.1007/978-3-642-67770-0_1 #4n

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, 1 Jan 1994; pp 74–91. 51 kB.

Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., John Wiley & Sons, Inc., 1 Jan 1981; pp 1109–1137. 4.7 MB. #29j

Shulgin, AT. Psychotomimetic agents. In Psychopharmacological Agents; Gordon, M, Ed., Academic Press, New York, 1 Jan 1976; Vol. 4, pp 59–146. 3.1 MB. #XXIV,XXVII

Taschwer, M; Ebner, E; Schmid, MG. Test purchase of new synthetic tryptamines via the Internet: Identity check by GC-MS and separation by HPLC. J. Appl. Pharm. Sci., 1 Jan 2016, 6 (1), 028–034. 504 kB. https://doi.org/10.7324/JAPS.2016.600105

Nagai, F; Nonaka, R; Kamimura, KSH. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. Eur. J. Pharmacol., 22 Mar 2007, 559 (2), 132–137. 399 kB. https://doi.org/10.1016/j.ejphar.2006.11.075 #AMT

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 #AMT

Seto, T; Takahashi, M; Nagashima, M; Suzuki, J; Yasuda, I. The identifications and the aspects of the commercially available uncontrolled drugs purchased between Apr. 2003 and Mar. 2004. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 75–80. 1.2 MB. #AMT MS,NMR,UV

Hoffer, A; Osmond, H. The Hallucinogens, Academic Press, New York, . 3.9 MB. #a-Methyltryptamine

Lloyd, DH; Nichols, DE. Nickel boride/hydrazine hydrate reduction of aromatic and aliphatic nitro compounds. Synthesis of 4-(benzyloxy)indole and α-alkyltryptamines. J. Org. Chem., 1 Oct 1986, 51 (22), 4294–4295. 327 kB. https://doi.org/10.1021/jo00372a037 #5a MS,NMR

Scott, KR; Power, JD; McDermott, SD; O’Brien, JE; Talbot, BN; Barry, MG; Kavanagh, PV. Identification of (2-aminopropyl)indole positional isomers in forensic samples. Drug Test. Anal., 1 Jul 2014, 6 (7–8), 598–606. 1.8 MB. https://doi.org/10.1002/dta.1508 #3-API GC,LC,MS,NMR,IR,TLC

Shulgin, AT; Nichols, DE. Characterization of three new psychotomimetics. In The Psychopharmacology of Hallucinogens; Stillman, RC; Willette, RE, Eds., Pergamon, 1 Jan 1978; pp 74–83. 210 kB. https://doi.org/10.1016/B978-0-08-021938-7.50010-2 #9 A different layout of the same paper

Glennon, RA; Young, R; Rosecrans, JA; Kallman, MJ. Hallucinogenic agents as discriminative stimuli: A correlation with serotonin receptor affinities. Psychopharmacology, 1 May 1980, 68 (2), 155–158. 395 kB. https://doi.org/10.1007/BF00432133 #α-MeT

Kraemer, M; Boehmer, A; Madea, B; Maas, A. Death cases involving certain new psychoactive substances: A review of the literature. Forensic Sci. Int., 1 May 2019, 298, 186–267. 6.7 MB. https://doi.org/10.1016/j.forsciint.2019.02.021 #α-Methyltryptamine

Kazushi, M; Kaori, S; Masashi, S; Yoshitsugu, M; Tsutomu, K. Analysis of tryptamines designated newly as narcotics. JCCL, 1 Jan 2005, (45), 77–87. 565 kB. #AMT Japanese, English abstract LC,MS,NMR,IR,UV

Yasuoka, T; Muroi, H; Okazaki, R; Matsumoto, Y; Terauchi, Y; Sasatani, T. Analysis of tryptamine group compounds. JCCL, 1 Jan 2003, (43), 63–69. 151 kB. #AMT Japanese, English abstract LC,MS,NMR,IR,UV

Barlow, RB; Khan, I. Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations. Br. J. Pharmacol., 1 Mar 1959, 14 (1), 99–107. 1.9 MB. https://doi.org/10.1111/j.1476-5381.1959.tb00934.x #17 other

Palamar, JJ; Acosta, P. A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines. Hum. Psychopharmacol. Clin. Exp., 1 Jan 2020, 35 (1), e2719. 764 kB. https://doi.org/10.1002/hup.2719 #AMT

Doi, K; Miyazawa, M; Fujii, H; Kojima, T. The analysis of the chemical drugs among structural isomer. Yakugaku Zasshi, 1 Sep 2006, 126 (9), 815–823. 371 kB. https://doi.org/10.1248/yakushi.126.815 #AMT GC,LC,MS,NMR,IR,TLC

Mesley, RJ; Evans, WH. Infrared identification of some hallucinogenic derivatives of tryptamine and amphetamine. J. Pharm. Pharmacol., 1 May 1970, 22 (5), 321–332. 775 kB. https://doi.org/10.1111/j.2042-7158.1970.tb08533.x #α-Methyltryptamine IR

Rudin, D; McCorvy, JD; Glatfelter, GC; Luethi, D; Szöllősi, D; Ljubišić, T; Kavanagh, PV; Dowling, G; Holy, M; Jaentsch, K; Walther, D; Brandt, SD; Stockner, T; Baumann, MH; Halberstadt, AL; Sitte, HH. (2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice. Neuropsychopharmacol., 1 Mar 2022, 47 (4), 914-923. 1.5 MB. https://doi.org/10.1038/s41386-021-01221-0 #3-API

Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #4.27

Glennon, RA; Rosecrans, JA. Indolealkylamine and phenalkylamine hallucinogens: A brief overview. Neurosci. Biobehav. Rev., 1 Jan 1982, 6 (4), 489–497. 895 kB. https://doi.org/10.1016/0149-7634(82)90030-6 #2a

McKenna, DJ; Towers, HHN. Biochemistry and pharmacology of tryptamines and beta-carbolines: A minireview. J. Psychoactive Drugs, 1 Jan 1984, 16 (4), 347–358. 10.8 MB. https://doi.org/10.1080/02791072.1984.10472305 #IT-290

N-Methyltryptamine · NMT

5-API · 5-IT

4-API · 4-IT · α-Me-isoT

5-Methyl-T · 5-Methyltryptamine

7-Methyl-T · 7-Methyltryptamine

6-API · 6-IT

7-API · 7-IT

Homotryptamine

3H-6-API · 3H-6-IT

3H-5-API · 3H-5-IT

Desmethyl fenproporex · PEA-P

1-API · 1-IT · iso-AMT · α-Methyl-isotryptamine

2-API · 2-IT

1-Methyl-T · 1-Methyltryptamine

2-Methyl-T · 2-Methyltryptamine

Gramine

N-Cyanomethyl-N-ethylbenzylamine

N-Cyanomethyl-N-Methylphenethylamine · N-NCMe-N-Me-PEA

8399

8397

p1-135: α-MT