PMID: 3761319Oct 1, 1986Paper

Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class

Journal of Medicinal Chemistry
D E NicholsA T Shulgin

Abstract

The alpha-ethyl phenethylamine derivative 1-(1,3-benzodioxol-5-yl)-2-butanamine was prepared. An asymmetric synthesis was used to prepare the enantiomers of this compound and the related alpha-methyl homologue (MDA). The racemates and enantiomers of both compounds were evaluated in the two-lever drug discrimination assay in rats trained to discriminate saline from 0.08 mg/kg of LSD tartrate. Stimulus generalization occurred with the racemate and the R-(-) enantiomer of the alpha-methyl homologue and the S-(+) enantiomer of the alpha-ethyl primary amine. No generalization occurred with the other enantiomers or with the N-methyl derivatives of either series. Human psychopharmacology studies revealed that the N-methyl derivative of the title compound was nonhallucinogenic and that it had a new, novel psychoactive effect. It is suggested that this compound is the prototype of a new pharmacologic class that may have value in facilitating psychotherapy and that this class be designated as entactogens.

Citations

Jan 2, 1989·European Journal of Pharmacology·J B Appel, P M Callahan
Jul 23, 1991·European Journal of Pharmacology·J F Nash, D E Nichols
Dec 8, 1992·European Journal of Pharmacology·X HuangD E Nichols
Jul 20, 1993·European Journal of Pharmacology·X Huang, D E Nichols
Jun 2, 1994·European Journal of Pharmacology·D Marona-Lewicka, D E Nichols
Dec 12, 1995·European Journal of Pharmacology·D Marona-LewickaD E Nichols
Sep 1, 1993·Talanta·J A SquellaL J Nuñez-Vergara
Mar 1, 1988·Pharmacology, Biochemistry, and Behavior·R A GlennonG Patrick
Dec 1, 1988·Pharmacology, Biochemistry, and Behavior·M D Schechter
May 1, 1989·Pharmacology, Biochemistry, and Behavior·M P Johnson, D E Nichols
Nov 1, 1989·Pharmacology, Biochemistry, and Behavior·D E NicholsM P Johnson
Mar 1, 1991·Pharmacology, Biochemistry, and Behavior·R Oberlender, D E Nichols
Feb 1, 1991·Pharmacology, Biochemistry, and Behavior·T D SteeleG K Yim
May 1, 1991·Pharmacology, Biochemistry, and Behavior·K Kirkpatrick-StegerI Gormezano
Jan 1, 1991·Pharmacology, Biochemistry, and Behavior·D E NicholsR Oberlender
Feb 1, 1996·Pharmacology, Biochemistry, and Behavior·L E Baker, M M Makhay
Jan 1, 1996·Behavioural Brain Research·M A Geyer
Jan 1, 1994·Brain Research Bulletin·M E BronsonJ DeRuiter
Jun 23, 2001·Pharmacology, Biochemistry, and Behavior·J B RangisettyR A Glennon
Mar 20, 2002·Pharmacology, Biochemistry, and Behavior·Richard A GlennonJagadeesh B Rangisetty
Aug 1, 1997·Pharmacology, Biochemistry, and Behavior·L E Baker, M M Taylor
Feb 26, 1998·Pharmacology, Biochemistry, and Behavior·M D Schechter
Mar 25, 1998·Pharmacology, Biochemistry, and Behavior·N V CozziD E Nichols
Mar 12, 1999·Neuroscience and Biobehavioral Reviews·K M HegadorenM Bourin
Jul 20, 2002·European Journal of Medicinal Chemistry·Sally Freeman, John F Alder
Jul 27, 2007·Neuropsychopharmacology : Official Publication of the American College of Neuropsychopharmacology·Boris MlinarRenato Corradetti
Nov 23, 2001·Journal of Psychoactive Drugs·A R Pentney
Jan 1, 1990·Annals of the New York Academy of Sciences·D E Nichols, R Oberlender
Jul 3, 2008·Journal of Psychopharmacology·Mw JohnsonRr Griffiths

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