107447-03-0Relevant articles and documents
HENRY CONDENSATION AT HIGH PRESSURES. 1. SYNTHESIS OF 1-(3,4-METHYLENEDIOXYPHENYL)-2-NITRO-1-BUTENE AND AN IMPROVED SYNTHESIS OF 1-(3,4-METHYLENEDIOXYPHENYL)-2-METHYLAMINOBUTANE
Azafonov, N. E.,Sedishev, I. P.,Zhulin, V. M.
, p. 738 - 741 (1990)
The hitherto inaccessible nitroolefin (VII), which is the most convenient intermediate for the synthesis of the psychotropic amine (VIII), has been obtained by the direct condensation at high pressures (up to 1500 MPa) of piperonal (V) with 1-nitropropane (VI).The structure of (VII) was confirmed by direct synthesis from pyrocatechol (X).The amine (VIII) was obtained in three steps from (VII).This synthesis of (VIII) is shorter than that previously reported.
Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: Representatives of a novel therapeutic class
Nichols,Hoffman,Oberlender,Jacob III,Shulgin
, p. 2009 - 2015 (2007/10/02)
The α-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 α-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 α-methyl homologue and the S-(+)enantiomer of the α-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.
