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. https://doi.org/10.1021/jm00176a010 #1
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. https://doi.org/10.1021/jm00234a010 #2e
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, 1 Jan 1978; pp 16–26. 502 kB. #3
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. https://doi.org/10.1016/0006-2952(83)90281-2 #α-EH-DOM
Partyka, RA; Standridge, RT; Howell, HG; Shulgin, AT. 2-Amino-1-(2,5-dimethoxyphenyl)butanes. Patent US 4105695, 8 Aug 1978. 645 kB. other
Shulgin, AT. Treatment of senile geriatric patients to restore performance. Patent US 4034113, 5 Jul 1977. 519 kB.
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. https://doi.org/10.1016/0091-3057(93)90379-8 #α-EH DOM
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.
Ger, A; Ger, D. Triple Goddess of the Night. Br. Neurosci. Assoc. Bull., 1 Mar 2011, 63, 28–30. 234 kB. #Ariadne Dmitri Ger is credited with the discovery of Jelena, also known as 2C-IP.
Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 24 Apr 2003; pp 67–137. 6.3 MB.
Nichols, DE; Oberlender, R. Structure-activity relationships of MDMA-like substances. In Pharmacology and Toxicology of Amphetamine and Related Designer Drugs. NIDA Research Monograph 94; Asghar, K; De Souza, E, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1989; pp 1-29. 282 kB. #4
Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., John Wiley & Sons, Inc., 1 Jan 1981; pp 1109–1137. 4.7 MB. #26
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. 8.1 MB. #44
Nichols, DF; Oberlender, R. Structure-activity relationships of MDMA and related compounds: A new class of psychoactive agents? In Ecstasy: The Clinical, Pharmacological and Neurotoxicological Effects of the Drug MDMA; Peroutka, SJ, Ed., Springer US, 1 Jan 1990; pp 105–131. 733 kB. https://doi.org/10.1007/978-1-4613-1485-1_7 #8
Jacob, JN; Nichols, DE. Isomeric cyclopropyl ring-methylated homologues of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analogue. J. Med. Chem., 1 Jul 1982, 25 (5), 526–530. 732 kB. https://doi.org/10.1021/jm00347a009 #2 NMR
Winter, JC. Effects of the phenethylamine derivatives, BL-3912, fenfluramine, and Sch-12679, in rats trained with LSD as a discriminative stimulus. Psychopharmacology, 1 May 1980, 68 (2), 159–162. 443 kB. https://doi.org/10.1007/BF00432134 #BL-3912
Tilson, HA; Chamberlain, JH; Gylys, JA. Behavioral comparisons of R-2-amino-1-(2,5-dimethoxy-4-methylphenyl) butane (BL-3912A) with R-DOM and S-amphetamine. Psychopharmacology, 1 Jan 1977, 51 (2), 169–173. 507 kB. https://doi.org/10.1007/BF00431735 #BL-3912A
Weintraub, HJR; Nichols, DE. Conformational energy calculations of some amphetamine analogs using a new solvation model. Int. J. Quantum Chem., 18 Jun 2009, 14 (S5), 321–343. 1.2 MB. https://doi.org/10.1002/qua.560140731 #II other
Oberlender, RA. Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 May 1989. 8.2 MB. #BL-3912 MS,NMR,IR,other
Halberstadt, AL; Chatha, M; Klein, AK; Wallach, J; Brandt, SD. Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species. Neuropharmacology, 1 May 2020, 167, 107933. 2.4 MB. https://doi.org/10.1016/j.neuropharm.2019.107933 #α-Et-2C-D
Cunningham, MJ; Bock, HA; Serrano, IC; Bechand, B; Vidyadhara, DJ; Bonniwell, EM; Lankri, D; Duggan, P; Nazarova, AL; Cao, AB; Calkins, MM; Khirsariya, P; Hwu, C; Katritch, V; Chandra, SS; McCorvy, JD; Sames, D. Pharmacological mechanism of the non-hallucinogenic 5-HT2A agonist Ariadne and analogs. ACS Chem. Neurosci., 15 Dec 2022, n/a. 15.3 MB. https://doi.org/10.1021/acschemneuro.2c00597 #32 MS,NMR,other
Kruegel, AC. Phenalkylamines and methods of making and using the same. Patent WO 2022/192781 A1, 15 Sep 2022. 22.8 MB. #25 LC,MS,NMR
Wallach, J; Cao, AB; Calkins, MM; Heim, AJ; Lanham, JK; Bonniwell, EM; Hennessey, JJ; Bock, HA; Anderson, EI; Sherwood, AM; Morris, H; de Klein, R; Klein, AK; Cuccurazzu, B; Gamrat, J; Fannana, T; Zauhar, R; Halberstadt, AL; McCorvy, JD. Identification of 5-HT2A receptor signaling pathways responsible for psychedelic potential. bioRxiv, 31 Jul 2023, 2023.07.29.551106. 9.8 MB. https://doi.org/10.1101/2023.07.29.551106 #α-Ethyl-2C-D LC,MS,NMR