Exploring 5-MeO-α-MT. To explore a different substance…

Names:
5-MeO-α-MT
α,O-DMS
Alpha-O
5-MeO-AMT
Tryptamine, 5-methoxy-α-methyl
Indole, 3-(2-aminopropyl)-5-methoxy
Serotonin, α,O-dimethyl
α,O-Dimethylserotonin
5-Methoxy-α-methyltryptamine
3-(2-Aminopropyl)-5-methoxyindole
IUPAC name:
1-(5-Methoxy-1H-indol-3-yl)propan-2-amine
5005 · C12H16N2O · 204.268
InChI=1S/C12H16N2O/c1-8(13)5-9-7-14-12-4-3-10(15-2)6-11(9)12/h3-4,6-8,14H,5,13H2,1-2H3
OGNJZVNNKBZFRM-UHFFFAOYSA-N This stereoisomer Any stereoisomer

Shulgin, AT; Nichols, DE. Characterization of three new psychotomimetics. In The Psychopharmacology of Hallucinogens; Stillman, RC; Willette, RE, Eds., Pergamon Press, New York, 1978; pp 74–84. 547 kB.

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

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

Shulgin, AT. Profiles of psychedelic drugs. 6 α-O-DMS. J. Psychedelic Drugs, 1 Jul 1979, 11 (3), 247–247. 684 kB. https://doi.org/10.1080/02791072.1979.10472112

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-HT1B receptors. J. Med. Chem., 1 Jan 1988, 31 (7), 1406–1412. 1.1 MB. https://doi.org/10.1021/jm00402a026

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.

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

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.

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.

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, CP. 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

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. Analysis, 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

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. 652 kB. https://doi.org/10.1007/7854_2016_466

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

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., 2003, 46 (19), 4188–2195. 126 kB. https://doi.org/10.1021/jm030205t #2a

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

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. 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, 1982; Vol. 55 (3), pp 3–29. 29.7 MB. #4o

Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., Wiley & Co., 1981; pp 1109–1137. 4.7 MB. #29k

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 Open access DOI

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 Open access DOI

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21 July 2018 · Creative Commons BY-NC-SA ·