Explore 3,4-Dimethoxyphenethylamine

PiHKAL book II entry DMPEA

ChemSpider 8114
PubChem 8421
Wikidata Q4634069
Wikipedia 3,4-Dimethoxyphenethylamine
Trout’s Notes 3,4-Dimethoxyphenethylamine. In The Cactus Alkaloids (2013, upd. 2018), pp. 63–66
Project Response Homoveratrylamine (1342-16)

Shulgin Index #49 DMPEA · Table 4Page 330Row 5

PiHKAL #20 2C-B · #115 MDPEA · #142 PEA · #152 2-TIM · #154 4-TIM

Phenethylamine: Von der Strucktur zur Funktion DMPEA: 7.5 (2) 549 · 7.5 (17) 552, 553 · 3,4-DMPEA: 8.6 (15) 883

Sargent, TW; Israelstam, DM; Shulgin, AT; Landaw, SA; Finley, NN. A note concerning the fate of the 4-methoxyl group in 3,4-dimethoxyphenethylamine (DMPEA). Biochem. Biophys. Res. Commun., 1 Jan 1967, 29 (1), 126–130. 262 kB. https://doi.org/10.1016/0006-291X(67)90552-9 #DMPEA

Sargent, T; Shulgin, AT; Kusubov, N. Quantitative measurement of demethylation of [14]C-methoxyl labeled DMPEA and TMA-2 in rats. Psychopharmacol. Commun., 1 Jan 1976, 2 (3), 199–206. 8.6 MB. #III

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 #2 MS,NMR,IR,TLC

Shulgin, AT; Sargent, T; Naranjo, C. Role of 3,4-dimethoxyphenethylamine in schizophrenia. Nature, 1 Jan 1966, 212, 1606–1607. 267 kB. https://doi.org/10.1038/2121606a0 #DMPEA

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 #XXXVIII

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 #II

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. #2 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 #57

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 #22 NMR

Ghosal, S; Srivastava, RS. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochemistry, 1 Jan 1973, 12 (1), 193–197. 552 kB. https://doi.org/10.1016/S0031-9422(00)84646-4 #III MS,NMR,IR,UV,TLC

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, 27 Aug 2002, 9, 1634–1638. 115 kB. https://doi.org/10.1039/b200607c

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-DMPEA 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 #20

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

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on dimethoxyphenethylamines (DMPEA): Regioisomers related to 2,5-DMPEA. J. Chromatogr. Sci., 1 Jan 2012, 50 (1), 1–9. 594 kB. https://doi.org/10.1093/chromsci/bmr013

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 #6 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 #49

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 #II

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. #Fig. 3.1

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 TLC

Smythies, JR; Sykes, EA. Structure-activity relationship studies on mescaline: The effect of dimethoxyphenylethylamine and N,N-dimethyl mescaline on the conditioned avoidance response in the rat. Psychopharmacologia, 1 Sep 1965, 8 (5), 324-330. 371 kB. https://doi.org/10.1007/BF00453510 #Dimethoxyphenylethylamine

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.

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. 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. #19d

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.

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.

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. #XLIX

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77 (4), 1245–1272. 1.2 MB. https://doi.org/10.1016/j.talanta.2008.07.062 #DMPEA GC,LC,MS,UV

Hoffer, A; Osmond, H. The Hallucinogens, Academic Press, New York, . 3.9 MB. #3,4-Dimethoxyphenylethylamine

Nichols, DE. Structure-activity relationships of phenethylamine hallucinogens. J. Pharm. Sci., 1 Aug 1981, 70 (8), 839–849. 1.4 MB. https://doi.org/10.1002/jps.2600700802 #VII

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 #XI

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 #2

Smythies, JR; Levy, CK. The comparative psychopharmacology of some mescaline analogues. Br. J. Psychiatry, 1 Jan 1960, 106 (443), 531–536. 637 kB. https://doi.org/10.1192/bjp.106.443.531 #II

Shulgin, AT. Mescaline: the chemistry and pharmacology of its analogs. Lloydia, 1 Jan 1973, 36 (1), 46–58. 5.6 MB. #10

Vogel, WH; Evans, BD. Structure-activity-relationships of certain hallucinogenic substances based on brain levels. Life Sci., 15 May 1977, 20 (10), 1629–1635. 419 kB. https://doi.org/10.1016/0024-3205(77)90335-6 #3,4-Dimethoxy-PEA

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 #23

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 #37

2,5-DMPEA · 2,5-Dimethoxyphenethylamine · 2C-H

3-Methoxy-N-methyltyramine · N-Me-GEA

2,4-DMPEA · 2,4-Dimethoxyphenethylamine · 24 · 24DMP

4-Methoxynorephedrine · β-HO-PMA

2,3-DMPEA · 2,3-Dimethoxyphenethylamine

2,6-DMPEA · 2,6-Dimethoxyphenethylamine

3,5-DMPEA · 3,5-Dimethoxyphenethylamine

4-HO-3-MeO-A · 4-Hydroxy-3-methoxyamphetamine · HMA · MHA

BO3M · β,3-Dimethoxyphenethylamine

β,4-Dihydroxy-N,N-dimethylphenethylamine · β-HO-Hordenine

β-O-Methylsynephrine · β-MeO-HMePEA

β,4-Dihydroxymethamphetamine · β-HO-HMA

β,4-DMPEA · β,4-Dimethoxyphenethylamine

N-Hydroxy-4-methoxyamphetamine · HOT-PMA

N,N-Dimethyl-2,3-dihydroxyphenethylamine · N,N-Me-2,3-DHPEA

α-Methyl-2-methoxy-4-hydroxyphenethylamine · β,2-MHPEA-3

2,4-HMA · 2-Hydroxy-4-methoxyamphetamine

N,N-Dimethyl-3,4-dihydroxyphenethylamine · N,N-Me-DHPEA

N-Et-DHPEA · N-Ethyl-3,4-dihydroxyphenethylamine

3,4-Dihydroxymethamphetamine · 3,4-HHMA · DHMA

DH-α-Et-PEA · α-Ethyl-3,4-dihydroxyphenethylamine

β-Me-GEA · β-Methyl-4-hydroxy-3-methoxyphenethylamine

N-Me-HMPEA · N-Methyl-3-hydroxy-4-methoxyphenethylamine

3-Hydroxy-4-methoxyamphetamine · HMA

N-Methyl-β,2-dihydroxy-5-methylphenethylamine · β,2-HO-5,N-MePEA

β,2-Dihydroxy-5-methylamphetamine · β,2-HO-5-MeA

β-HO-2-M-5-MePEA · β-Hydroxy-2-methoxy-5-methylphenethylamine

2,5-HMA · 2-Hydroxy-5-methoxyamphetamine

2,5-DES-Me-DOM · 2,5-Dihydroxy-4-methylamphetamine

597

3-Hydroxy-2-methoxyamphetamine · HMA

5-Hydroxy-2-methoxyamphetamine · 5HMA

748

N-Et-β,3-HPEA · N-Ethyl-β,3-dihydroxyphenethylamine · Etilefrine

β,3-DHMA · β,3-Dihydroxymethamphetamine

12414

AEME · Methylecgonidine

3-Methoxy-2-trideuteromethoxyphenethylamine · IS

Longimammine

p1-107: DMPEA: Subjective response