Explore 3,4-Dimethoxyamphetamine

PiHKAL book II entry 3,4-DMA

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PubChem 8423
Wikidata Q27277248
Wikipedia Dimethoxyamphetamine
swgdrug.org 3,4-Dimethoxyamphetamine
Rhodium Optically pure amphetamines by the way of α-methylhydrocinnamic acid

Shulgin Index #38 DMA · Table 4Page 330Row 17

PiHKAL #53 2,4-DMA · #124 META-DOB · #157 TMA

Phenethylamine: Von der Strucktur zur Funktion 3,4-DMA: 7.1 (35) 467 · 7.2 (50) 479 · 7.5 (18) 549, 552

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 #3 MS,NMR,IR,TLC

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 #VI

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8.6 MB. #DMA

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 other

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 #5b

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. #3 External examiner: A. T. Shulgin! NMR,IR,UV,TLC

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 #56

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 #3,4-DMA NMR

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 other

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; pp 243–333. 2.6 MB. https://doi.org/10.1007/978-1-4757-0510-2_6 #30 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 #48

Bailey, K; Legauld, D; Verner, D. Spectroscopic and chromatographic identification of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., , 57 (1), 70–78. 426 kB. #3,4-DMA GC,LC,NMR,IR,UV,TLC

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 #VI

Eichmeier, LS; Caplis, ME. The forensic chemist. An “analytical detective”. Anal. Chem., 1 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. Anal., 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 GC,MS,IR

Vidal Giné, C; Espinosa, IF; Vilamala, MV. New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon? Drug Test. Anal., 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, 24 Apr 2003; pp 67–137. 6.3 MB.

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.

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, 1 Jan 1978; pp 199–217. 623 kB. #3

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 #10l

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. #22j

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. 8.1 MB.

Biel, JH; Bopp, BA. Amphetamines: Structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; 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, 1 Jan 1976; Vol. 4, pp 59–146. 3.1 MB. #LXIX

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 NMR,IR,other

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., 1 Oct 2006, 19 (10), 1294–2304. 204 kB. https://doi.org/10.1021/tx060123i #12 MS,NMR,other

Marcher-Rørsted, E; Halberstadt, AL; Klein, AK; Chatha, M; Jademyr, S; Jensen, AA; Kristensen, JL. Investigation of the 2,5-dimethoxy motif in phenethylamine serotonin 2A receptor agonists. ACS Chem. Neurosci., 26 Mar 2020, 11 (9), 1238-1244. 3.8 MB. https://doi.org/10.1021/acschemneuro.0c00129 #14 LC,MS,NMR

Hägele, JS; Basrak, M; Schmid, MG. Enantioselective separation of novel psychoactive substances using a Lux® AMP 3 μm column and HPLC-UV. J. Pharm. Biomed. Anal., 5 Feb 2020, 179, 112967. 3.6 MB. https://doi.org/10.1016/j.jpba.2019.112967 #A8 LC

Clancy, L; Philp, M; Shimmon, R; Fu, S. Development and validation of a color spot test method for the presumptive detection of 25-NBOMe compounds. Drug Test. Anal., 19 Aug 2020, 13 (5), 929-943. 11.3 MB. https://doi.org/10.1002/dta.2905 #3,4-dimethoxyamphetamine

Bailey, K; Legault, D. The use of carbon-13 nuclear magnetic resonance spectra in the identification and authentication of monomethoxyamphetamines and dimethoxyamphetamines. J. Forensic Sci., 1 Jan 1981, 26 (1), 27–34. 366 kB. https://doi.org/10.1520/JFS11326J #3,4-diOCH3 NMR

Philp, M; Shimmon, R; Stojanovska, N; Tahtouh, M; Fu, S. Development and validation of a presumptive colour spot test method for the detection of piperazine analogues in seized illicit materials. Anal. Methods, 1 Jan 2013, 5 (20), 5402. 783 kB. https://doi.org/10.1039/c3ay40511g #3,4-Dimethoxyamphetamine MS,NMR,IR,spot

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Shulgin, AT. Psychotomimetic agents related to the catecholamines. J. Psychedelic Drugs, 1 Apr 1969, 2 (2), 14–19. 782 kB. https://doi.org/10.1080/02791072.1969.10524409 #XIIc

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Shulgin, AT; Sargent, T; Naranjo, C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. In Ethnopharmacologic Search for Psychoactive Drugs; Efron, DH; Holmstedt, B; Kline, NS, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 28 Jan 1967; pp 202–215. 951 kB. #DMA

Shulgin, AT. Mescaline: the chemistry and pharmacology of its analogs. Lloydia, 1 Jan 1973, 36 (1), 46–58. 5.6 MB. #21

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 15 Aug 1977, 21 (4), 569–576. 320 kB. https://doi.org/10.1016/0024-3205(77)90099-6 #22

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Gupta, SP; Singh, P; Bindal, MC. QSAR studies on hallucinogens. Chem. Rev., 1 Dec 1983, 83 (6), 633–649. 2.8 MB. https://doi.org/10.1021/cr00058a003 #30, 49

2,5-Dimethoxy-4-methylphenethylamine · 2C-D · LE-25

3,5-Dimethoxy-4-methylphenethylamine · DESOXY

2,4-DMA · 2,4-Dimethoxyamphetamine

2,5-DMA · 2,5-Dimethoxyamphetamine · DMA · DOH

3-Methoxy-4-ethoxyphenethylamine · MEPEA

3,5-DMA · 3,5-Dimethoxyamphetamine

2,3-DMA · 2,3-Dimethoxyamphetamine

2,6-DMA · 2,6-Dimethoxyamphetamine

3-Methoxy-N,N-dimethyltyramine · MM-GEA

25H-NMe · N-Me-2,5-DMPEA

2,5-MH-MMA · 5-Hydroxy-2-methoxymethamphetamine · 5HMP

2-DES-Me-DOM · 2-DM-DOM · 2-HMMP

5-DES-Me-DOM · 5-DM-DOM

4-Me-2,6-DMPEA · ψ-2C-D

2407

4-Ethoxynorephedrine · β-Hydroxy-4-ethoxyamphetamine

N-Methyl-β,3-dimethoxyphenethylamine · BO3MM

BO3ME · β-Ethoxy-3-methoxyphenethylamine

BO3MA · β,3-Dimethoxyamphetamine

BO3E · β-Methoxy-3-ethoxyphenethylamine

N-Me-DMPEA-2 · N-Methyl-2,3-dimethoxyphenethylamine

2,3-EMPEA · 2-Ethoxy-3-methoxyphenethylamine

N-Me-DMPEA-3 · N-Methyl-2,4-dimethoxyphenethylamine

2,4-EMPEA · 2-Ethoxy-4-methoxyphenethylamine

N,N,N-Trimethyl-3,4-dihydroxyphenethylamine⁺ · Coryneine

N,N-Dimethyl-3,4-dihydroxyamphetamine · N,N-Me-DHA

N-Ethyl-3,4-dihydroxyamphetamine · DHEA

4-HO-3-MeO-MA · 4-Hydroxy-3-methoxymethamphetamine · HMMA · MHMA

MH-α-Et-PEA · α-Ethyl-4-hydroxy-3-methoxyphenethylamine

3-Hydroxy-4-methoxymethamphetamine · HMMA

β-Me-DMPEA · β-Methyl-3,4-dimethoxyphenethylamine

N-Me-DMPEA · N-Methyl-3,4-dimethoxyphenethylamine

3-Ethoxy-4-methoxyphenethylamine · EMPEA

β,2-Dihydroxy-5-methylmethamphetamine · β,2-HO-5,N-DMeA

β-HO-N-Me-2-M-5-MePEA · β-Hydroxy-2-methoxy-N,5-dimethylphenethylamine

β-HO-2-M-5-MeA · β-Hydroxy-2-methoxy-5-methylamphetamine

N,N-Dimethyl-2-hydroxy-5-methoxyphenethylamine · N,N-Me-2,5-HMPEA

β-Me-2,5-DMPEA · β-Methyl-2,5-dimethoxyphenethylamine

N-Me-3,5-DMPEA · N-Methyl-3,5-dimethoxyphenethylamine

N-Me-2,6-DMPEA · N-Methyl-2,6-dimethoxyphenethylamine

2,4-Dimethoxy-6-methylphenethylamine · 6-Me-2,4-DMPEA

3-Methyl-2,4-dimethoxyphenethylamine · iso-2C-D

3-Hydroxy-2-methoxymethamphetamine · HMP

N,4-Dimethoxyamphetamine · N-MeO-PMA

homo-3,4-DMPEA

N-Isopropyl-2,3-dihydroxyphenethylamine · N-iPr-2,3-DHPEA

5,2-EMPEA · 5-Ethoxy-2-methoxyphenethylamine

N-Pr-3,4-DHPEA · N-Propyl-3,4-dihydroxyphenethylamine

N-Isopropyl-4-hydroxyphenethylamine N-oxide · N-iPr-4-MPEA N-oxide

N-Isopropyl-β,4-dihyydroxyphenethylamine · Deterenol

6948

β-O-Ethyl-synephrine

12680

p1-143: 3,4-DMA