Exploring MEM. To explore a different substance…

Names:
MEM · 2,5-Dimethoxy-4-ethoxyamphetamine
IUPAC name:
1-(4-Ethoxy-2,5-dimethoxyphenyl)propan-2-amine
ID: 122 · Formula: C13H21NO3 · Molecular weight: 239.311
InChI: InChI=1S/C13H21NO3/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. http://dx.doi.org/10.1016/S0376-8716(99)00148-9

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. http://dx.doi.org/10.1021/bk-1989-0413.ch018

By, AW; Dawson, BA; Lodge, BA; Neville, GA; Sy, W; Zamecnik, J. Synthesis and spectral properties of 2,5-dimethoxy-4-ethoxyamphetamine and its precursors. J. Forensic Sci., 1 Mar 1990, 35 (2), 316–335. 538 kB. http://dx.doi.org/10.1520/JFS12833J

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. http://dx.doi.org/10.3109/00498259209056689

Corrigall, WA; Coen, KM; Saouda, FM; Robertson, JM; Lodge, BA. Discriminative stimulus properties of substituted amphetamine derivatives. Pharmacol. Biochem. Behav., 1 Dec 1992, 43 (4), 1117–1119. 265 kB. http://dx.doi.org/10.1016/0091-3057(92)90490-7

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; Vol. 11, pp 243–333. 2584 kB. http://dx.doi.org/10.1007/978-1-4757-0510-2_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. http://dx.doi.org/10.1016/j.bmc.2003.10.027

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. http://dx.doi.org/10.1016/0014-2999(81)90106-0

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). European Journal of Pharmacology, 15 Jun 1984, 102 (1), 23–29. 461 kB. http://dx.doi.org/10.1016/0014-2999(84)90333-9

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. 8647 kB.

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. http://dx.doi.org/10.1021/jm00307a056

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. http://dx.doi.org/10.1371/journal.pone.0009019

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Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. http://dx.doi.org/10.1016/j.neuropharm.2011.01.017

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N-Acetyl MEM
2C-O-2
4C-EtO
EEM
ALEPH
ALEPH-2
ALEPH-4
ALEPH-6
ALEPH-7
2,5-DMA
DOAM
DOB
DOBU
DOC
DOEF
DOET
DOI
DOM
DON
DOPR
MPM
TMA-2
DOF
DOIB
DOTB
DOSB
DONH · DOA
DOAA
Hydroxy-DOPR
DOIP
MIPM
MBM
MAM
DOHE
DOBZ
DOCPM
ALEPH-8
ALEPH-5
ALEPH-16
ALEPH-21
DOTFM
2328
DOYN
DOCN
DOPh3
2325
2329
2330
DOVI
DOAC
DOCA
DOOH
DOCONHP
DOCOE
DOCEB
DOCEP
DOOC
DONMM
DOFM
DOHM
DOHP
DONO
DOEH
M(2OP)M
M(3OP)M
MBZM
ALEPH-19
ALEPH-S-amyl
ALEPH-S-PhEt
ALEPH sulfone
DOTFE
MTFEM
MDFEM
MFEM
DOBM
DOMCl
DOCET
DOTFPR
DOHSM
DOMSM
DOMOM
DONCO
DONCOE
DONCOTFM
DOCNM
1016
MEE
AEM
ASB
3C-E
2C-O-4
EMM
IP
MME
MP
P
SB
189
4C-TMPEA-6
BOED
Z-7.2
Trichocerine
N-Me-TMA · METHYL-TMA
N-Me-TMA-2 · METHYL-TMA-2
N-Me-TMA-6 · METHYL-TMA-6
2C-O-7
Salbutamol
homo-TMA-2
homo-TMA-3
homo-TMA-6
N,N-Me-β,3,4-TMPEA
β-HO-β,N,N-Me-2,5-DMPEA
β-HO-N,N-Me-2,5-DMA
β-HO-N-Me-2,5-DEPEA
β-HO-2,5-DEA
N-Me-TMA-3
4C-TMPEA-3
4C-HM
BOE
DOEH
4C-MeO
DESMETHYL-iPr
α-MM-M
DOMOM
N-Acetyl MEM
2C-O-2
4C-EtO
EEM
ALEPH
ALEPH-2
ALEPH-4
ALEPH-6
ALEPH-7
2,5-DMA
DOAM
DOB
DOBU
DOC
DOEF
DOET
DOI
DOM
DON
DOPR
MPM
TMA-2
DOF
DOIB
DOTB
DOSB
DONH · DOA
DOAA
Hydroxy-DOPR
DOIP
MIPM
MBM
MAM
DOHE
DOBZ
DOCPM
ALEPH-8
ALEPH-5
ALEPH-16
ALEPH-21
DOTFM
2328
DOYN
DOCN
DOPh3
2325
2329
2330
DOVI
DOAC
DOCA
DOOH
DOCONHP
DOCOE
DOCEB
DOCEP
DOOC
DONMM
DOFM
DOHM
DOHP
DONO
DOEH
M(2OP)M
M(3OP)M
MBZM
ALEPH-19
ALEPH-S-amyl
ALEPH-S-PhEt
ALEPH sulfone
DOTFE
MTFEM
MDFEM
MFEM
DOBM
DOMCl
DOCET
DOTFPR
DOHSM
DOMSM
DOMOM
DONCO
DONCOE
DONCOTFM
DOCNM
1016
MEE
AEM
ASB
3C-E
2C-O-4
EMM
IP
MME
MP
P
SB
189
4C-TMPEA-6
BOED
Z-7.2
Trichocerine
N-Me-TMA · METHYL-TMA
N-Me-TMA-2 · METHYL-TMA-2
N-Me-TMA-6 · METHYL-TMA-6
2C-O-7
Salbutamol
homo-TMA-2
homo-TMA-3
homo-TMA-6
N,N-Me-β,3,4-TMPEA
β-HO-β,N,N-Me-2,5-DMPEA
β-HO-N,N-Me-2,5-DMA
β-HO-N-Me-2,5-DEPEA
β-HO-2,5-DEA
N-Me-TMA-3
4C-TMPEA-3
4C-HM
BOE
DOEH
4C-MeO
DESMETHYL-iPr
α-MM-M
DOMOM
10 December 2016 · Creative Commons BY-NC-SA ·