Exploring DOET. To explore a different substance…

Names:
DOET · HECATE · 2,5-Dimethoxy-4-ethylamphetamine · 4-Ethyl-2,5-dimethoxyamphetamine
IUPAC name:
1-(4-Ethyl-2,5-dimethoxyphenyl)propan-2-amine
ID: 66 · Formula: C13H21NO2 · Molecular weight: 223.311
InChI: InChI=1S/C13H21NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h7-9H,5-6,14H2,1-4H3

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

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1.1 MB. http://dx.doi.org/10.1021/jm00082a014

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. http://dx.doi.org/10.1021/jm00165a023

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. http://dx.doi.org/10.1021/jm00177a017

Shulgin, AT; Dyer, DC. Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem., 1 Jan 1975, 18 (12), 1201–1204. 534 kB. http://dx.doi.org/10.1021/jm00246a006

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1.2 MB. http://dx.doi.org/10.1021/jm00256a016

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. http://dx.doi.org/10.1021/jm00263a013

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

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.

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. 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 8–15. 457 kB.

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1970; pp 21–41. 8.6 MB.

Snyder, SH; Weingartner, H; Faillace, LA. DOET (2,5-dimethoxy-4-ethylamphetamine) and DOM (STP) (2,5-dimethoxy-4-methylamphetamine), new psychotropic agents: Their effects in man. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1970; pp 247–264. 2.5 MB.

Fenderson5555. DOC, DOB, DOI and DOET: Strategic considerations. 7 Sep 2013. 9.5 MB.

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.

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. 4.4 MB. http://dx.doi.org/10.1021/bk-1989-0413.ch018

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

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. http://dx.doi.org/10.1016/j.bmc.2008.02.033

Snyder, SH; Weingartner, H; Faillace, LA. DOET (2,5-dimethoxy-4-ethylamphetamine), a new psychotropic drug. Arch. Gen. Psychiat., 1 Jan 1971, 24 (1), 50–55. 643 kB. http://dx.doi.org/10.1001/archpsyc.1971.01750070052006

Snyder, SH; Unger, S; Blatchley, R; Barfknecht, CF. Stereospecific actions of DOET (2,5-dimethoxy-4-ethylamphetamine). Arch. Gen. Psychiat., 1 Jul 1974, 31 (1), 103–106. 642 kB. http://dx.doi.org/10.1001/archpsyc.1974.01760130079013

Weingartner, H; Snyder, SH; Faillace, LA; Markley, H. Altered free associations: Some cognitive effects of DOET (2,5-dimethoxy-4-ethylamphetamine). Syst. Res., 1 Jul 1970, 15 (4), 297–303. 539 kB. http://dx.doi.org/10.1002/bs.3830150402

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Analysis, 1 Jul 2012, 4 (7-8), 577-590. 1.0 MB. http://dx.doi.org/10.1002/dta.413

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.

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

Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. http://dx.doi.org/10.1016/0024-3205(73)90079-9

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. http://dx.doi.org/10.1016/0024-3205(77)90099-6

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

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. http://dx.doi.org/10.1016/S0968-0896(03)00437-1

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; Young, R; Rosecrans, JA. A comparison of the behavioral effects of DOM homologs. Pharmacol. Biochem. Behav., 1 Apr 1982, 16 (4), 557–559. 256 kB. http://dx.doi.org/10.1016/0091-3057(82)90414-2

Glennon, RA; Titeler, M; McKenney, JD. Evidence for 5-HT2 involvement in the mechanism of action of hallucinogenic agents. Life Sci., 17 Dec 1984, 35 (25), 2505–2511. 332 kB. http://dx.doi.org/10.1016/0024-3205(84)90436-3

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. http://dx.doi.org/10.1016/0024-3205(78)90053-X

2C-E
4C-E
α-Cl-2C-E
2-TOET
532
G-12
G-22
ALEPH
ALEPH-2
ALEPH-4
ALEPH-6
ALEPH-7
2,5-DMA
DOAM
DOB
DOBU
DOC
DOEF
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
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
5-TOET
ARIADNE
BEATRICE
2C-P
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
2C-E
4C-E
α-Cl-2C-E
2-TOET
532
G-12
G-22
ALEPH
ALEPH-2
ALEPH-4
ALEPH-6
ALEPH-7
2,5-DMA
DOAM
DOB
DOBU
DOC
DOEF
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
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
5-TOET
ARIADNE
BEATRICE
2C-P
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
24 June 2017 · Creative Commons BY-NC-SA ·