Exploring ARIADNE. To explore a different substance…

Names:
ARIADNE · 4C-DOM · BL-3912 · Dimoxamine · 2,5-Dimethoxy-α-ethyl-4-methylphenethylamine · 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminobutane
IUPAC name:
1-(2,5-Dimethoxy-4-methylphenyl)butan-2-amine
ID: 8 · Formula: C13H21NO2 · Molecular weight: 223.311
InChI: InChI=1S/C13H21NO2/c1-5-11(14)7-10-8-12(15-3)9(2)6-13(10)16-4/h6,8,11H,5,7,14H2,1-4H3

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. http://dx.doi.org/10.1016/0006-2952(83)90281-2

Shulgin, AT. Treatment of senile geriatric patients to restore performance. U S. Patent 4,034,113, 5 Jul 1977. 519 kB.

Shulgin, AT; Shulgin, LA; Jacob, P. A protocol for the evaluation of new psychoactive drugs. Meth. Find. Exp. Clin. Pharmacol., 1 May 1986, 8 (5), 313. 7.9 MB.

Partyka, RA; Standridge, RT; Howell, HG; Shulgin, AT. 2-Amino-1-(2,5-dimethoxyphenyl)butanes. U.S. Patent 4,105,695, 8 Aug 1978. 645 kB.

Barfknecht, CF; Caputo, JF; Tobin, MB; Dyer, DC; Standridge, RT; Howell, HG; Goodwin, WR; Partyka, RA; Gylys, JA; Cavanagh, RL. Congeners of DOM: Effect of distribution on the evaluation of pharmacologic data. 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, 1978; pp 16–26. 502 kB.

Ger, A; Ger, D. Triple Goddess of the Night. Br. Neurosci. Assoc. Bull., 1 Mar 2011, 63, 28–30. 234 kB. Dmitri Ger is credited with the discovery of Jelena, also known as 2C-IP.

Standridge, RT; Howell, HG; Gylys, JA; Partyka, RA; Shulgin, AT. Phenylalkylamines with potential psychotherapeutic utility. 1. 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)butane. J. Med. Chem., 1 Jan 1976, 19 (12), 1400 –1404. 730 kB. http://dx.doi.org/10.1021/jm00234a010

Standridge, RT; Howell, HG; Tilson, HA; Chamberlain, JH; Holava, HM; Gylys, JA; Partyka, RA; Shulgin, AT. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. J. Med. Chem., 1 Jan 1980, 23 (2), 154–162. 1.1 MB. http://dx.doi.org/10.1021/jm00176a010

Glennon, RA. MDMA-like stimulus effects of α-ethyltryptamine and the α-ethyl homolog of DOM. Pharmacol. Biochem. Behav., 1 Oct 1993, 46 (2), 459–462. 396 kB. http://dx.doi.org/10.1016/0091-3057(93)90379-8

189
2C-D
DOM
α-Me-DOM · CHARMIAN
α-Carboxy-2C-D
α-Carboxy-DOM
1210
4C-DMA · 4C-H
4C-DOB
4C-DOI
4C-E
4C-IP
4C-T
4C-DOPR
4C-BU
4C-HO
4C-EtO
4C-PrO
4C-iPrO
4C-DON
4C-NH
4C-DOC
4C-HM
4C-HE
4C-TMA-2
4C-T-2
4C-T-7
1209
DMCPA
α-CP-2C-D
DOMAI · DOM-AI
DOMAT · DOM-AT
DMMCPA
HO-DOMAI
DMMCPA
DMCBA
BEATRICE
2C-P
DOET
GANESHA
IRIS
JUNO
N,N-Me-2C-D
2C-D-2,5-DIEtO · 2CD-2,5-DIETO
2CE-5ETO
2,5-DNNA
2,6-DNNA
3,5-DNNA
α-Me-DOM · CHARMIAN
DAPHNE
ELVIRA
FLORENCE
2,4-DNNA
2155
25H-NPro
2C-IP
4,2,6-DOET · ψ-DOET
4-Butoxynorephedrine
homo-N,N-Me-2,5-DMPEA
homo-DOM
BO3MIP
β-HO-N-Pr-PMA
4C-2,3-DMPEA
N,N-Me-2,3-EMPEA
N,N-Me-DMA
6622
N,N-Me-3,4-EMPEA
N,N-Me-4,3-EMPEA
N-Me-DEPEA
DEA
β,N,N-Me-2,5-DMPEA
4,2,3-DOET
3,2,4-DOET
2,3,4-DOET
5,2,3-DOET
3,2,5-DOET
2,3,5-DOET
5,2,4-DOET
β,β-Me-2C-D
β-Me-DOM
2,4,5-DOET
4,3,5-DOET
3,4,5-DOET
6,2,3-DOET
3,2,6-DOET
2,3,6-DOET
2,4,6-DOET
4-Me-2,6-MEA
6-Me-2,4-DEPEA
2C-G-21
2C-G-12
3,4,6-Me-2,5-DMPEA
IPOMA
POMA
189
2C-D
DOM
α-Me-DOM · CHARMIAN
α-Carboxy-2C-D
α-Carboxy-DOM
1210
4C-DMA · 4C-H
4C-DOB
4C-DOI
4C-E
4C-IP
4C-T
4C-DOPR
4C-BU
4C-HO
4C-EtO
4C-PrO
4C-iPrO
4C-DON
4C-NH
4C-DOC
4C-HM
4C-HE
4C-TMA-2
4C-T-2
4C-T-7
1209
DMCPA
α-CP-2C-D
DOMAI · DOM-AI
DOMAT · DOM-AT
DMMCPA
HO-DOMAI
DMMCPA
DMCBA
BEATRICE
2C-P
DOET
GANESHA
IRIS
JUNO
N,N-Me-2C-D
2C-D-2,5-DIEtO · 2CD-2,5-DIETO
2CE-5ETO
2,5-DNNA
2,6-DNNA
3,5-DNNA
α-Me-DOM · CHARMIAN
DAPHNE
ELVIRA
FLORENCE
2,4-DNNA
2155
25H-NPro
2C-IP
4,2,6-DOET · ψ-DOET
4-Butoxynorephedrine
homo-N,N-Me-2,5-DMPEA
homo-DOM
BO3MIP
β-HO-N-Pr-PMA
4C-2,3-DMPEA
N,N-Me-2,3-EMPEA
N,N-Me-DMA
6622
N,N-Me-3,4-EMPEA
N,N-Me-4,3-EMPEA
N-Me-DEPEA
DEA
β,N,N-Me-2,5-DMPEA
4,2,3-DOET
3,2,4-DOET
2,3,4-DOET
5,2,3-DOET
3,2,5-DOET
2,3,5-DOET
5,2,4-DOET
β,β-Me-2C-D
β-Me-DOM
2,4,5-DOET
4,3,5-DOET
3,4,5-DOET
6,2,3-DOET
3,2,6-DOET
2,3,6-DOET
2,4,6-DOET
4-Me-2,6-MEA
6-Me-2,4-DEPEA
2C-G-21
2C-G-12
3,4,6-Me-2,5-DMPEA
IPOMA
POMA
19 November 2017 · Creative Commons BY-NC-SA ·