Allenic Amines: A New Class of Nonhydrazine MAO Inhibitors

Synthesis and monoamine oxidase inhibitory activities of .alpha.-allenic amines in vivo and in vitro. Different activities of two enantiomeric allenes

“…In conclusion, we have shown, by extending the observations of Halliday et al,14 that several different types of amines bearing a 2,3-butadienyl chain are quite potent inhibitors of MAO. From our work it can be concluded that, depending on the substitution pattern, these inhibitors can be of either A or B type.…”

“…In the case of pargyline, the structure of the adduct has been determined. 13 The structure of the adduct formed between the allenic amine 1, a known inhibitor of MAO,14 In connection with this work, we have developed new synthetic methods for a-allenic amines, which are generally useful and are particularly suited for the preparation of labeled allenic amines needed in the above studies.17,18…”

“…The allenic inhibitors can be divided into two gross structural classes, namely, (i) an arylalkylamine class with a 2,3-butadienyl substituent on the nitrogen (compounds 1,2, and [10][11][12][13][14] and (ii) a class comprising compounds 3-9, which are 2-phenylor 2-benzyl-substituted 2,3-butadienylamines. The structural unit, NCH2C=C=C, was kept intact in the two series, since an -methyl substituent, as in compound 15, most likely interferes with the oxidation by MAO, resulting in a poor inhibitor (cf.…”