3,4-DMA
DMA
EA-1316
3,4-Dimethoxyamphetamine
 
1-(3,4-Dimethoxyphenyl)propan-2-amine
 55 ·  C11H17NO2 ·  195.258
 InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)11(7-9)14-3/h4-5,7-8H,6,12H2,1-3H3
 KAZPHAGSWZTKDW-UHFFFAOYSA-N This stereoisomer Any stereoisomer
 COc1cc(ccc1OC)CC(N)C

Butterick, JR; Unrau, AM. Studies on theoretical psychotogens. Synthesis of O-methylated analogs of catecholamine neurotransmitters and metabolic precursors. Can. J. Chem., 1 Jan 1974, 52 (16), 2873–2879. 305 kB. https://doi.org/10.1139/v74-418

Barfknecht, CF; Nichols, DE. Effects of S-(+)- and R-(-)-3,4,dimethoxyphenylisopropylamines in the rat. J. Med. Chem., 1 Jan 1972, 15 (1), 109–110. 295 kB. https://doi.org/10.1021/jm00271a037

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

Scorza, MC; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. https://doi.org/10.1016/S0006-2952(97)00405-X #10

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.

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. https://doi.org/10.1021/jm00144a009

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 May 1973, 16 (5), 480–483. 515 kB. https://doi.org/10.1021/jm00263a013

Butterick, JR. Synthesis of O-transmethylated catecholamines and psychodysleptic β-phenylisopropylamines. Ph. D. Thesis, Simon Faser University, Burnaby, BC, Canada, 11 Mar 1975. 6.1 MB. External examiner: A. T. Shulgin!

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

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 #23 NMR

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 #11

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. https://doi.org/10.1007/BF02137743

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.

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. https://doi.org/10.1016/0014-2999(81)90106-0 #3,4-DMA

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

Bailey, K; Legauld, D; Verner, D. Spectroscopic and chromatographic identification of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1974, 57 (1), 70–78. 426 kB.

Shannon, M; Battaglia, G; Glennon, RA; Titeler, M. 5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA). Eur. J. Pharmacol., 15 Jun 1984, 102 (1), 23–29. 461 kB. https://doi.org/10.1016/0014-2999(84)90333-9 #3,4-DMA

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

Eichmeier, LS; Caplis, ME. The forensic chemist. An “analytical detective”. Anal. Chem., Aug 1975, 47 (9), 841A–844a. 1.6 MB. https://doi.org/10.1021/ac60359a050

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, 1 Jan 2018, 10 (1), 72-80. 206 kB. https://doi.org/10.1002/dta.2292

Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #3.8

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC–MS and GC–IRD studies on dimethoxyamphetamines (DMA): Regioisomers related to 2,5-DMA. Forensic Sci. Int., 1 Jan 2009, 192 (1-3), 115-125. 1.0 MB. https://doi.org/10.1016/j.forsciint.2009.08.010

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

Caspar, AT; Meyer, MR; Westphal, F; Weber, AA; Maurer, HH. Nano liquid chromatography-high-resolution mass spectrometry for the identification of metabolites of the two new psychoactive substances N-(ortho-methoxybenzyl)-3,4-dimethoxyamphetamine and N-(ortho-methoxybenzyl)-4-methylmethamphetamine. Talanta, 1 Oct 2018, 188 111–123. 1.7 MB. https://doi.org/10.1016/j.talanta.2018.05.064 #D3

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, 1 Jan 1994; pp 3–41. 6.9 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, 1982; Vol. 55 (3), pp 3–29. 29.7 MB. #10l

Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., Wiley & Co., 1981; pp 1109–1137. 4.7 MB. #22j

Anderson, GM; Castagnoli, N; Kollman, PA. Quantitative structure-activity relationships in the 2,4,5-ring-substituted phenylisopropylamines. 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 199–217. 623 kB. #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, 1 Jan 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. #LXIX

Milhazes, N; Cunha-Oliveira, T; Martins, P; Garrido, J; Oliveira, C; Rego, AC; Borges, F. Synthesis and cytotoxic profile of 3,4-methylenedioxymethamphetamine (“Ecstasy”) and its metabolites on undifferentiated PC12 cells: A putative structure-toxicity relationship. Chem. Res. Toxicol., 2006, 19 (10), 1294–2304. 204 kB. https://doi.org/10.1021/tx060123i #12

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. #35

2C-D
DESOXY
2,4-DMA
2,5-DMA
MEPEA
3,5-DMA
2,3-DMA
2,6-DMA
MM-GEA
N-Me-2,5-DMPEA · 25H-NMe
2,5-MH-MMA
2-DES-Me-DOM · 2-DM-DOM
5-DES-Me-DOM · 5-DM-DOM
4-Me-2,6-DMPEA · ψ-2C-D
2407
4-Ethoxynorephedrine
BO3MM
BO3ME
BO3MA
BO3E
N-Me-DMPEA-2
2,3-EMPEA
N-Me-DMPEA-3
2,4-EMPEA
Coryneine
N,N-Me-DHA
DHEA
MHMA
MH-α-Et-PEA
HMMA
β-Me-DMPEA
N-Me-DMPEA
EMPEA
β,2-HO-5,N-DMeA
β-HO-N-Me-2-M-5-MePEA
β-HO-2-M-5-MeA
N,N-Me-2,5-HMPEA
β-Me-2,5-DMPEA
N-Me-3,5-DMPEA
N-Me-2,6-DMPEA
6-Me-2,4-DMPEA
iso-2C-D
HMP
homo-3,4-DMPEA
N-MeO-PMA
10139
10088
10037
Isopropyloctopamine
  3,4-DMA
16 November 2018 · Creative Commons BY-NC-SA ·