Explore 2,4-Dimethoxyamphetamine

PiHKAL book II entry 2,4-DMA

ChemSpider 124411
PubChem 141047
Wikidata Q27279269
Wikipedia Dimethoxyamphetamine

Shulgin Index #35 2,4-DMA · Table 4Page 327Row 11

PiHKAL #55 3,4-DMA · #124 META-DOB · #157 TMA

Phenethylamine: Von der Strucktur zur Funktion 2,4-DMA: 7.1 (33) 467 · 7.2 (5) 475, 477, 478, 479, 483, 484

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 #12

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 #III

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. #2,4-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

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT_1C and 5-HT₂ serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1.1 MB. https://doi.org/10.1021/jm00082a014 #14 NMR

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 #27

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 #16 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 #2,4-DMA NMR

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 #31 Rhodium.

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 #34

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 #2,4-DMA

Bailey, K; Legauld, D; Verner, D. Spectroscopic and chromatographic identification of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., , 57 (1), 70–78. 426 kB. #2,4-DMA GC,LC,NMR,IR,UV,TLC

Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #3.6

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

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

King, LA. New phenethylamines in Europe. Drug Test. Anal., 1 Jul 2014, 6 (7-8), 808-818. 472 kB. https://doi.org/10.1002/dta.1570

Titeler, M; Lyon, RA; Glennon, RA. Radioligand binding evidence implicates the brain 5-HT₂ receptor as a site of action for LSD and phenylisopropylamine hallucinogens. Psychopharmacology, 1 Feb 1988, 94 (2), 213–216. 431 kB. https://doi.org/10.1007/BF00176847 #14

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.

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. #1

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. 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. #22h

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. 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 #10j

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. #LXX

EMCDDA. New drugs in Europe, 2006, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2007. 375 kB. #2,4-DMA

Klagges, J; Burgos-Villaseca, J; Benavente-Schonhaut, S; Malhue, V; Hernandez, A; Burgos, H; Castro-Castillo, V; Sáez-Briones, P. Behavioral characterization of the acute effects in rats of 2,4-DMA (2,4-dimethoxyamphetamine) as precursor of atypical psychotropic derivatives. ResearchGate, 23 Sep 2015. 312 kB. https://doi.org/10.13140/RG.2.1.3507.8167 #2,4-DMA

Sáez-Briones, P; Hernández, A. MDMA (3,4-Methylenedioxymethamphetamine) Analogues as Tools to Characterize MDMA-Like Effects: An Approach to Understand Entactogen Pharmacology. Curr. Neuropharmacol., 1 Sep 2013, 11 (5), 521–534. 1.4 MB. https://doi.org/10.2174/1570159X11311050007 #2,4-DMA

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 #13 LC,MS,NMR

Flanagan, TW; Billac, GB; Landry, AN; Sebastian, MN; Cormier, SA; Nichols, CD. Structure–activity relationship analysis of psychedelics in a rat model of asthma reveals the anti-inflammatory pharmacophore. ACS Pharmacol. Transl. Sci., 9 Apr 2021, 4 (2), 488-502. 13.3 MB. https://doi.org/10.1021/acsptsci.0c00063 #2,4-DMA

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 #2,4-diOCH3 NMR

Clare, BW. Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters. J. Med. Chem., 1 Feb 1990, 33 (2), 687–702. 2.8 MB. https://doi.org/10.1021/jm00164a036 #36

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. #2,4-DMA

Shulgin, AT. Mescaline: the chemistry and pharmacology of its analogs. Lloydia, 1 Jan 1973, 36 (1), 46–58. 5.6 MB. #22

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 #8

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

3,5-Dimethoxy-4-methylphenethylamine · DESOXY

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

3,4-DMA · 3,4-Dimethoxyamphetamine · DMA · EA-1316

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

p1-144: 2,4-DMA