Exploring ψ-DOM. To explore a different substance…

Names:
ψ-DOM
Z-7
4-Methyl-2,6-dimethoxyamphetamine
2,6-Dimethoxy-4-methylamphetamine
IUPAC name:
1-(2,6-Dimethoxy-4-methylphenyl)propan-2-amine
69 · C12H19NO2 · 209.285
InChI=1S/C12H19NO2/c1-8-5-11(14-3)10(7-9(2)13)12(6-8)15-4/h5-6,9H,7,13H2,1-4H3
CFFJUEYUTHKVMQ-UHFFFAOYSA-N This stereoisomer Any stereoisomer
COc1cc(C)cc(c1CC(N)C)OC

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 #12

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

Chambers, JJ; Kurrasch-Orbaugh, DM; Nichols, DE. Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: Effects on 5-HT2A/2C receptor affinity. Bioorg. Med. Chem. Lett., 1 Aug 2002, 12 (15), 1997–1999. 100 kB. https://doi.org/10.1016/S0960-894X(02)00306-2 #2

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!

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 #4-Me-2,6-DMA

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 #52

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. #39

2C-E
2C-G
DOM
2,5-DMMA · METHYL-DMA
4C-DMA · 4C-H
4C-DMPEA
N-Me-2C-D
2C-D-2-EtO · 2CD-2ETO
2C-D-5-EtO · 2CD-5ETO
m-DOM · 5-DOM
o-DOM · 2-DOM
6-Me-2,4-DOM · Z-7.1
2,4-DMMA
ψ-2C-E
4-Propoxynorephedrine
homo-DMA
homo-N-Me-2,5-DMPEA
BO3MDM
BO3MEA
BO3EE
BO3P
N,N-Me-DMPEA-2
N-Me-2,3-DMA
N-Me-2,3-EMPEA
4C-2,4-DMPEA
2,4-DEPEA
N-Me,N-iPr-DHPEA
N-Bu-DHPEA
N-iBu-DHPEA
MHEA
N-Me-α-Et-GEA
Salicifoline
HMEA
N,N-Me-DMPEA
N-Et-DMPEA
DMMA
N-Me-EMPEA
EMA
MEA
DEPEA
β-HO-N-Me-2-M-5-MeA
N,N-Me-2,5-HMA
N,N-Me-2C-H
β,N-Me-2,5-DMPEA
N,N-Me-3,5-DMPEA
N-Me-3,5-DMA
N,N-Me-2,6-DMPEA
N-Me-2,6-DMA
4-Me-2,3-DOM
3-Me-2,4-DOM
2-Me-3,4-DOM
5-Me-2,3-DOM
3-DOM
2-Me-3,5-DOM
BMD
5-Me-3,4-DOM
4-Me-3,5-DOM
6-Me-2,3-DOM
3-Me-2,6-DOM
2-Me-3,6-DOM
6-Me-2,4-EMPEA
2C-H-2-iPrO
10432
10408
DE
10096
10048
10034
10027
3,5-DMB
2C-H-5-iPrO
17 October 2018 · Creative Commons BY-NC-SA ·