Exploring M. To explore a different substance…

Names:
M
EA-1306
Mescaline
3,4,5-Trimethoxyphenethylamine
IUPAC name:
2-(3,4,5-Trimethoxyphenyl)ethan-1-amine
96 · C11H17NO3 · 211.258
Peyote alkaloid
InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3
RHCSKNNOAZULRK-UHFFFAOYSA-N This stereoisomer Any stereoisomer

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. https://doi.org/10.1016/j.bmc.2008.02.033

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. https://doi.org/10.1002/cmdc.200800133

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

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Analysis, 1 Jul 2012, 4 (7-8), 577-590. 1.0 MB. https://doi.org/10.1002/dta.413

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

Meyers-Riggs, B. Leminger’s scalines. countyourculture, countyourculture: rational exploration of the underground, 4 May 2012.

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. https://doi.org/10.1124/jpet.106.117507

Ogunbodede, O; McCombs, D; Trout, K; Daley, PF; Terry, M. New mescaline concentrations from 14 taxa/cultivars of Echinopsis spp. (Cactaceae) (“San Pedro”) and their relevance to shamanic practice. J. Ethnopharmacol., 15 Sep 2010, 131 (2), 356–362. 324 kB. https://doi.org/10.1016/j.jep.2010.07.021

Battersby, A; Binks, R; Huxtable, R. Biosynthesis of cactus alkaloids. Tetrahedron Lett., 1 Jan 1967, 8 (6), 563–565. 134 kB. https://doi.org/10.1016/S0040-4039(00)90548-3

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. https://doi.org/10.1016/j.pbb.2007.06.001

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. https://doi.org/10.1038/221537a0

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1970; pp 21–41. 8.6 MB.

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. https://doi.org/10.1016/0024-3205(77)90099-6

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. https://doi.org/10.1016/0027-5107(77)90210-X

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. https://doi.org/10.1002/jps.2600680733

Shulgin, AT. Profiles of psychedelic drugs. 7. Mescaline. J. Psychedelic Drugs, 1 Jan 1979, 11 (4), 355. 1.3 MB. https://doi.org/10.1080/02791072.1979.10471421

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1.2 MB. https://doi.org/10.1021/jm00373a013

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1.8 MB. https://doi.org/10.1111/j.2042-7158.1985.tb03072.x

Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5.9 MB.

Desantis, F; Nieforth, KA. Synthesis of potential mescaline antagonists. J. Pharm. Sci., 1 Jan 1976, 65 (10), 1479–1484. 704 kB. https://doi.org/10.1002/jps.2600651016

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. https://doi.org/10.1016/S0968-0896(03)00437-1

Ho, B; Tansey, LW; Balster, RL; An, R; McIsaac, WM; Harris, RT. Amphetamine analogs. II. Methylated phenethylamines. J. Med. Chem., 1 Jan 1970, 13 (1), 134–135. 278 kB. https://doi.org/10.1021/jm00295a034

Friedhoff, AJ; Goldstein, M. New developments in metabolism of mescaline and related amines. Ann. N. Y. Acad. Sci., 1 Jan 1962, 96, 5–13. 506 kB. https://doi.org/10.1111/j.1749-6632.1962.tb50097.x

Daly, J; Axelrod, J; Witkop, B. Methylation and demethylation in relation to the in vitro metabolism of mescaline. Ann. N. Y. Acad. Sci., 1 Jan 1962, 96, 37–43. 397 kB. https://doi.org/10.1111/j.1749-6632.1962.tb50099.x #I MS,NMR,IR,TLC

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. https://doi.org/10.1021/jm00177a017

Smythies, JR. The mescaline phenomena. Br. J. Philos. Sci., 1 Feb 1953, 3 (12), 339–347. 72 kB. https://doi.org/10.1093/bjps/III.12.339

Fenderson5555. Two syntheses of mescaline. , 21 Mar 2011. . Fenderson5555 2.2 MB.

Reviriego, F; Navarro, P; Domènech, A; García-España, E. Effective complexation of psychotropic phenethylammonium salts from a disodium dipyrazolate salt of macrocyclic structure. J. Chem. Soc. Perkin Trans. 2, 2002, 1634–1638. 115 kB. https://doi.org/10.1039/b200607c

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2). 775 kB. https://doi.org/10.4172/2161-0495.1000108

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. https://doi.org/10.1002/omr.1270210611

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. https://doi.org/10.1021/jm00295a007

Short, JH; Dunnigan, DA; Ours, CW. Synthesis of phenethylamines from phenylacetonitriles obtained by alkylation of cyanide ion with Mannich bases from phenols and other benzylamines. Tetrahedron, 1973, 29 (14), 1931–1939. 791 kB. https://doi.org/10.1016/0040-4020(73)80127-9

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. https://doi.org/10.1021/jm00327a016

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. https://doi.org/10.1016/0024-3205(78)90053-X

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1978; Vol. 11, pp 243–333. 2.6 MB. https://doi.org/10.1007/978-1-4757-0510-2_6 Rhodium.

Makriyannis, A; Bowerman, D; Sze, PY; Fournier, D; De Jong., AP. Structure activity correlations in the inhibition of brain synaptosomal 3H-norepinephrine uptake by phenethylamine analogs. The role of α-alkyl side chain and methoxyl ring substitutions. Eur. J. Pharmacol., 9 Jul 1982, 81 (2), 337–340. 313 kB. https://doi.org/10.1016/0014-2999(82)90454-X

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. https://doi.org/10.1016/j.bmc.2003.10.027

Walters, GC; Cooper, PD. Alicyclic analogue of mescaline. Nature, 20 Apr 1968, 218 (5138), 298–300. 3.1 MB. https://doi.org/10.1038/218298a0

Zaehner, RC. The menace of mescalin. New Blackfriars, 1 Jul 1954, 35 (412–413), 310–323. 848 kB. https://doi.org/10.1111/j.1741-2005.1954.tb06115.x

Hermle, L; Fünfgeld, M; Oepen, G; Botsch, H; Borchardt, D; Gouzoulis, E; Fehrenbach, RA; Spitzer, M. Mescaline-induced psychopathological, neuropsychological, and neurometabolic effects in normal subjects: Experimental psychosis as a tool for psychiatric research. Biol. Psychiat., 1 Dec 1992, 32 (11), 976–991. 1.6 MB. https://doi.org/10.1016/0006-3223(92)90059-9

Hardman, HF; Haavik, CO; Seevers, MH. Relationship of the structure of mescaline and seven analogs to toxicity and behavior in five species of laboratory animals. Toxicol. Appl. Pharmacol., 1 Jun 1973, 25 (2), 299–309. 751 kB. https://doi.org/10.1016/S0041-008X(73)80016-X

Sreenivasan, V. Problems in Identification of Methylenedioxy and Methoxy Amphetamines. J. Crim. Law Criminol., 1 Jan 1972, 63 (2), 304. 996 kB.

Passie, T; Benzenhöfer, U. MDA, MDMA and other mescaline-like substances in the US military’s search for a truth drug (1940s to 1960s). Drug Test. Analysis, 31 Aug 2017, 10 (1), 72-80. 206 kB. https://doi.org/10.1002/dta.2292

Swanson, LR. Unifying theories of psychedelic drug effects. Front. Pharmacol., 2 Mar 2018, 9 n/a. 1.7 MB. https://doi.org/10.3389/fphar.2018.00172

Rickli, A; Luethi, D; Reinisch, J; Buchy, D; Hoener, MC; Liechti, ME. Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs). Neuropharmacology, 1 Dec 2015, 99 546–553. 625 kB. https://doi.org/10.1016/j.neuropharm.2015.08.034 #Mescaline

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

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

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 #33

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

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 #30

Halpern, JH; Lerner, AG; Passie, T. A review of hallucinogen persisting perception disorder (HPPD) and an exploratory study of subjects claiming symptoms of HPPD. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 333-360. 579 kB. https://doi.org/10.1007/7854_2016_457

Bogenschutz, MP; Ross, S. Therapeutic applications of classic hallucinogens. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 361-391. 360 kB. https://doi.org/10.1007/7854_2016_464

López-Giménez, JF; González-Maeso, J. Hallucinogens and serotonin 5-HT2A receptor-mediated signaling pathways. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 45-73. 712 kB. https://doi.org/10.1007/7854_2017_478

Nichols, DE. Psychedelics. Pharmacol. Rev., 1 Apr 2016, 68 (2), 264-355. 1.9 MB. https://doi.org/10.1124/pr.115.011478 Updated with published correction to Figure 4 (the α-methyl group was missing in the original)

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

Vidal Giné, C; Espinosa, IF; Vilamala, MV. New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon? Drug Test. Analysis, 1 Jul 2014, 6 (7-8), 819-824. 113 kB. https://doi.org/10.1002/dta.1610

Helm, K. Synthese und funktionelle In-vitro-Pharmakologie neuer Liganden des 5-HT2A-Rezeptors aus der Klasse. Ph. D. Thesis, Universität Regensburg, Dresden, 1 Jan 2014. 3.2 MB. #28

Nichols, DE. Structure-activity relationships of serotonin 5-HT2A agonists. WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. https://doi.org/10.1002/wmts.42 #32

Cassels, BK; Sáez-Briones, P. Dark classics in chemical neuroscience: Mescaline. ACS Chem. Neurosci., 8 Jun 2018, n/a. 424 kB. https://doi.org/10.1021/acschemneuro.8b00215

Ernst, SR; Cagle, FW. Mescaline hydrobromide. Acta Crystallogr. B, 1 Jul 1973, 29 (7), 1543–1546. 346 kB. https://doi.org/10.1107/S0567740873004917 #Mescaline

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.

Nichols, DE. Medicinal chemistry and structure-activity relationships. In Amphetamine and its Analogs; Cho, AK; Segal, DS, Eds., Academic Press, San Diego, CA, 1994; pp 3–41. 6.9 MB. #29

Nichols, DE; Oberlender, R. Structure-activity relationships of MDMA-like substances. In Pharmacology and Toxicology of Amphetamine and Related Designer Drugs. NIDA Research Monograph 94; Asghar, K; De Souza, E, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1989; pp 12–40. 282 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. #10a

Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., Wiley & Co., 1981; pp 1109–1137. 4.7 MB. #3

Braun, U; Braun, G; Jacob, P; Nichols, DE; Shulgin, AT. Mescaline Analogs: Substitutions at the 4-Position. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1978; pp 27–37. 497 kB. Rhodium.

Biel, JH; Bopp, BA. Amphetamines: Structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1978; Vol. 11, pp 1–39. 1.0 MB. https://doi.org/10.1007/978-1-4757-0510-2_1

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

Martins, D. Analysis of new psychoactive substances: A contribution to forensic chemistry. M. Sc. Thesis, Universidade do Porto, 1 Jan 2014. #6

Nichols, DE. Potential psychotomimetics: Bromomethoxyamphetamines and structural congeners of lysergic acid. Ph. D. Thesis, University of Iowa, Iowa City, IA, 1 May 1973. 13.0 MB. #1

Anon. New ways with hallucinogens. Lancet, 8 Mar 1969, 293 (7593), 510. 181 kB. https://doi.org/10.1016/S0140-6736(69)91603-1 #mescaline

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

BOHD
4-D
β-D
IM
TMPEA
TMPEA-5 · 2C-TMA-5
TMPEA-6 · 2C-TMA-6
3,5-D
2,6-D
α-D
N-Me-3-DESMETHYL
DOOH
β-HO-2,5-DMA
β,3,4-HO-N-iPr-DHPEA · Isoprenaline
MHMAOH
N,N-Me-HME
N-Me-DME
β,3,4-TMPEA
DMAOH
β-HO-DMA
β-HO-4,3-EMPEA
β,2-HO-N-Me-5-MA
β-HO-N-Me-2,5-DMPEA
BODM
β-HO,Me-2,5-DMPEA
β,2-HO-N-Me-5-EPEA
β,2-HO-5-EA
β-HO-N-Me-3,5-DMPEA
β-HO-N-Me-2,6-DMPEA
TMPEA-4
N-HO-2C-D
α-Me-3-DESMETHYL
DESMETHYL-M
α-Me-DESMETHYL
10030
Orciprenaline
N-Methyl-3,4,5-trimethoxybenzylamine
α,β-D
10252
10066
5-DM-TMA-2
2-DM-TMA-2
19 September 2018 · Creative Commons BY-NC-SA ·