Explore 5-Methoxy-α-methyltryptamine

TiHKAL book II entry α,O-DMS

ChemSpider 33864
PubChem 36906
Wikidata Q4031586
Erowid 5-MeO-AMT
Wikipedia 5-MeO-AMT
Wikipedia, see also List of substituted α-alkyltryptamines
Blotter 5-MeO-α-MT
Project Response 5-MeO-AMT (3146-22)
bluelight.org 5-MeO-AMT Scraps
hyperlab.info 5-MeO-AMT
bluelight.org The Big & Dandy 5-MeO-AMT Thread
swgdrug.org 5-Methoxy-α-methyltryptamine (5-MeO-AMT)
Rhodium Shulgin & Nichols: Three new psychotomimetics: para-DOT - MDMA - α,O-DMS (11)
bluelight.org 5-MeO-AMT Effects and Ratings Survey Results

PiHKAL #15 BOH

TiHKAL #48 α-MT · #55 α,N,O-TMS

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 #11 A different layout of the same paper

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 MS

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

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 #5 NMR,IR

Shulgin, AT. Profiles of psychedelic drugs. 6 α-O-DMS. J. Psychedelic Drugs, 1 Jul 1979, 11 (3), 247–247. 453 kB. https://doi.org/10.1080/02791072.1979.10472112 #α-O-DMS

Kantor, RE; Dudlettes, SD; Shulgin, AT. 5-Methoxy-alpha-methyltryptamine (alpha,O-dimethylserotonine) a hallucinogenic homolog of serotonin. Biol. Psychiat., 1 Jan 1980, 15, 349–352. 873 kB.

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 #1c NMR

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

Zimmerman, MM. The identification of 5-methoxy-alpha-methyltryptamine (5-MeO-AMT). Microgram J., 1 Jul 2003, 1 (3–4), 158–162. 269 kB. MS

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 #S16

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. 1.2 MB. https://doi.org/10.1124/jpet.111.179705

Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines. Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB. GC,LC,MS,NMR,IR,spot

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. #12 MS

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 #39

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

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 #60

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

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

Rickli, A; Moning, OD; Hoener, MC; Liechti, ME. Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens. Eur. Neuropsychopharmacol., 1 Aug 2016, 26 (8), 1327-1337. 845 kB. https://doi.org/10.1016/j.euroneuro.2016.05.001

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

Hyperlab. Hyperlab new compounds. 29 Sep 2014. 232 kB. Note: Contains links to hyperlab.info that require elevated access/karma to follow.

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., 1 Sep 2003, 46 (19), 4188–4195. 126 kB. https://doi.org/10.1021/jm030205t #2a MS,NMR

May, JA; Dantanarayana, AP; Zinke, PW; McLaughlin, MA; Sharif, NA. 1-((S)-2-Aminopropyl)-1H-indazol-6-ol: A potent peripherally acting 5-HT₂ receptor agonist with ocular hypotensive activity. J. Med. Chem., 12 Jan 2006, 49 (1), 318–328. 124 kB. https://doi.org/10.1021/jm050663x #19 MS,NMR

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. 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 #4o

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. 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. #29k

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 #5-Meo-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 #5-MeO-AMT GC,LC,MS,UV

EMCDDA. New drugs in Europe, 2005, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2006. 1.2 MB. #5MeO-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. #5-MeO-AMT MS,NMR,UV

Nagashima, M; Seto, T; Takahashi, M; Suzuki, J; Yasuda, I. Spectrum data of the 3rd Governor-designated drugs and the analyses of uncontrolled drugs purchased Apr. 2005 – Mar. 2006. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2006, 57 109–113. 394 kB. #5-MeO-AMT

Zamberlan, F; Sanz, C; Vivot, RM; Pallavicini, C; Erowid, F; Erowid, E; Tagliazucchi, E. The varieties of the psychedelic experience: A preliminary study of the association between the reported subjective effects and the binding affinity profiles of substituted phenethylamines and tryptamines. Front. Integr. Neurosci., 8 Nov 2018, 12 (54). 5.0 MB. https://doi.org/10.3389/fnint.2018.00054 #5-MeO-AMT

Luethi, D; Liechti, ME. Monoamine transporter and receptor interaction profiles in vitro predict reported human doses of novel psychoactive stimulants and psychedelics. Int. J. Neuropsychoph., 1 Oct 2018, 21 (10), 926–931. 254 kB. https://doi.org/10.1093/ijnp/pyy047 #S2 Tryptamines 5-MeO-AMT

Heim, R. Synthesis and pharmacology of potent 5-HT_2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. 3.9 MB. #4 In German. MS,NMR,IR

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. #5-MeO-AMT Japanese, English abstract LC,MS,NMR,IR,UV

Halberstadt, AL; Chatha, M; Klein, AK; Wallach, J; Brandt, SD. Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species. Neuropharmacology, 1 May 2020, 167, 107933. 2.4 MB. https://doi.org/10.1016/j.neuropharm.2019.107933 #5-MeO-AMT

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 #5-MeO-AMT

Kikura-Hanajiri, R; Kawamura, M; Uchiyama, N; Ogata, J; Kamakura, H; Saisho, K; Goda, Y. Analytical data of designated substances (shitei-yakubutsu) controlled by the pharmaceutical affairs law in Japan, Part I: GC-MS and LC-MS. Yakugaku Zasshi, 1 Jun 2008, 128 (6), 971–979. 1.4 MB. https://doi.org/10.1248/yakushi.128.971 #5-MeO-AMT Incorrect structures drawn. Corrected structures in errata page at end. GC,LC,MS,UV

Uchiyama, N; Kawamura, M; Kamakura, H; Kikura-Hanajiri, R; Goda, Y. Analytical data of designated substances (shitei-yakubutsu) controlled by the pharmaceutical affairs law in Japan, Part II: Color test and TLC. Yakugaku Zasshi, 1 Jan 2008, 128 (6), 981–987. 406 kB. https://doi.org/10.1248/yakushi.128.981 #5-MeO-AMT TLC

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 #2b

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 #5-Methoxy-α-methyl-tryptamine

4-HO-DMT · 4-Hydroxy-N,N-dimethyltryptamine · CX-59 · PAL-153 · PSOH · Psilocin

5-HO-DMT · 5-Hydroxy-N,N-dimethyltryptamine · Bufotenin

5-MeO-NMT · 5-Methoxy-N-methyltryptamine · N,O-DMS · nor-5-MeO-DMT

6-HO-DMT · 6-Hydroxy-N,N-dimethyltryptamine · 6-Hydroxy-DMT

7-MeO-NMT · 7-Methoxy-N-methyltryptamine

4-MeO-NMT · 4-Methoxy-N-methyltryptamine

7-HO-DMT · 7-Hydroxy-N,N-dimethyltryptamine

N,N-Dimethyltryptamine N-oxide · DMT N-oxide

5246

4-HO-iso-DMT · 4-Hydroxy-N,N-dimethyl-isotryptamine

4-MeO-AMT · 4-Methoxy-α-methyltryptamine

6-MeO-AMT · 6-Methoxy-α-methyltryptamine

5-EtO-T · 5-Ethoxytryptamine

1495

2,O-DMS · 2-Methyl-5-MeO-T · 2-Methyl-5-methoxytryptamine

4-Isopropylaminorex

N-Ethyl-4-methylaminorex

N,N,4-Trimethylaminorex

1-Methyl-5-MeO-T · 1-Methyl-5-methoxytryptamine

7-Methyl-5-MeO-T · 7-Methyl-5-methoxytryptamine

BNZMP

2-MBOP

3-MBOP

4-MBOP

Nebracetam

4-HO-AET · 4-Hydroxy-α-ethyltryptamine

11928

5-Methoxygramine

7-HO-NET · 7-Hydroxy-N-ethyltryptamine

p1-184: α,O-DMS
p1-196: Subjective effects of α,O-DMS
p2-252: α,O-DMS
p2-286: α,O-DMS