ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 19, Number 3
JKCSEZ 19(3)
June 20, 1975 

The intermediate, 17α-methyl-4-aza-5α-androstan-17β-ol(Ⅸ) required for the synthesis of 4-(β-guanidinoethyl)-17α-methyl-4-aza-5α-androstan-17β-ol(V) was obtained through a reaction of 17α-methyl-3,5-seco-4-norandrostan-17β-ol-5-on-3-oic acid(Ⅵ) with ammonium hydroxide followed by two reductions(platinum dioxide with hydrogen and lithium aluminium hydride). Condensation of Ⅸ with chloroacetonitrile under anhydrous condition, followed by reduction of the nitrile with lithium aluminium hydride gave 4-(β-aminoethyl)-17α-methyl-4-aza-5α-androstan-17β-ol(ⅩⅠ). The reaction of ⅩⅠ with 2-methyl-2-thiopseudourea or 3,5-dimethylpyrazole-1-carboxamidine, or cyanamide provided the title compound, V. Relaxation of the nictitating membrane, in the absence of mydriasis, is considered to be evidence of adrenergic neurone blockade. Thus the test compound(V) resembles that of the classical adrenergic neurone blocking agents.