Exploring ALEPH-2. To explore a different substance…

Names:
ALEPH-2 · 2,5-Dimethoxy-4-ethylthioamphetamine · 4-Ethylthio-2,5-dimethoxyamphetamine
IUPAC name:
1-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]propan-2-amine
ID: 4 · Formula: C13H21NO2S · Molecular weight: 255.376
InChI: InChI=1S/C13H21NO2S/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

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. http://dx.doi.org/10.1007/978-1-4757-0510-2_6 Rhodium.

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5.5 MB.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB.

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

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. http://dx.doi.org/10.1111/j.1471-4159.2005.03477.x

Rezende, MC; Núñez, C; Sepúlveda-Boza, S; Cassels, BK; Hurtado-Guzmán, C. S-Oxidation products of alkylthioamphetamines. Synth. Commun., 1 Jan 2002, 32 (17), 2741–2750. 225 kB. http://dx.doi.org/10.1081/SCC-120006041

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. http://dx.doi.org/10.1021/jm0493109

Acuña-Castillo, C; Scorza, C; Reyes-Parada, M; Cassels, BK; Huidobro-Toro, J. ALEPH-2, a suspected anxiolytic and putative hallucinogenic phenylisopropylamine derivative, is a 5-HT2A and 5-HT2C receptor agonist. Life Sci., 17 Nov 2000, 67 (26), 3241–3247. 89 kB. http://dx.doi.org/10.1016/S0024-3205(00)00906-1

Scorza, M; 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. http://dx.doi.org/10.1016/S0006-2952(97)00405-X

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

Scorza, MC; Reyes-Parada, M; Silveira, R; Viola, H; Medina, JH; Viana, MB; Zangrossi, H; Graeff, FG. Behavioral effects of the putative anxiolytic (±)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2) in rats and mice. Pharmacol. Biochem. Behav., 1 May 1996, 54 (2), 355–361. 504 kB. http://dx.doi.org/10.1016/0091-3057(95)02149-3

Reyes-Parada, M; Scorza, C; Romero, V; Silveira, R; Medina, JH; Andrus, D; Nichols, DE; Cassels, BK. (±)-1-(2,5-Dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2), a novel putative anxiolytic agent lacking affinity for benzodiazepine sites and serotonin-1A receptors. N-S. Arch. Pharmacol., 1 Nov 1996, 354 (5), 579–585. 1.4 MB. http://dx.doi.org/10.1007/BF00170831

N-Me-ALEPH-2
2C-T-2
4C-T-2
ALEPH
ALEPH-4
ALEPH-6
ALEPH-7
2,5-DMA
DOAM
DOB
DOBU
DOC
DOEF
DOET
DOI
DOM
DON
DOPR
MEM
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
DODMeA
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
Hydroxy-DOM
2C-T-4
ψ-2C-T-4
2C-T-7
3-TASB
4-TASB
5-TASB
TP
3-TSB
4-TSB
2CT2-2ETO
2CT2-5ETO
4C-T
2,4,3-2C-T-7
3,4,2-2C-T-7
2,3,4-2C-T-7
3,5,2-2C-T-7
2,3,5-2C-T-7
4,5,2-2C-T-7
N-Me-ALEPH
3,4,5-2C-T-7
2,6,3-2C-T-7
3,6,2-2C-T-7
2,3,6-2C-T-7
4,6,2-2C-T-7
ψ-ALEPH-2
ψ-2C-T-7
DOMSM
N-Me-ALEPH-2
2C-T-2
4C-T-2
ALEPH
ALEPH-4
ALEPH-6
ALEPH-7
2,5-DMA
DOAM
DOB
DOBU
DOC
DOEF
DOET
DOI
DOM
DON
DOPR
MEM
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
DODMeA
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
Hydroxy-DOM
2C-T-4
ψ-2C-T-4
2C-T-7
3-TASB
4-TASB
5-TASB
TP
3-TSB
4-TSB
2CT2-2ETO
2CT2-5ETO
4C-T
2,4,3-2C-T-7
3,4,2-2C-T-7
2,3,4-2C-T-7
3,5,2-2C-T-7
2,3,5-2C-T-7
4,5,2-2C-T-7
N-Me-ALEPH
3,4,5-2C-T-7
2,6,3-2C-T-7
3,6,2-2C-T-7
2,3,6-2C-T-7
4,6,2-2C-T-7
ψ-ALEPH-2
ψ-2C-T-7
DOMSM
19 November 2017 · Creative Commons BY-NC-SA ·