The metabolism of 3-amino-1-chloropropan-2-ol in relation to its antifertility activity in male rats

Abstract

1. The metabolism of 3-amino[³⁶Cl]chloropropan-2-ol (III) was studied in male rats. Three urinary metabolites were isolated and identified as α-chlorohydrin (I), β-chlorolactic acid (V) and oxalic acid (VI). Much of the administered aminochloropropanol was excreted unchanged in the urine; 63% within 72 h, 75% over 250 h.

2. Monoamine oxidase is capable of converting aminochloropropanol to β-chlorolactaldehyde (IV) which, by processes of either reduction or oxidation, suggests that the metabolic pathway is IV→I and IV→V→VI.

3. As assessed by the diuretic activities of the isomers of aminochloropropanol, oxalate appears to be produced by the (+)-isomer but not by the (-)-isomer. A difference in metabolic rate or route of the isomers may account for their differing physiological activities.

4. (+)- and (-)-aminochloropropanol exhibited identical in vitro inhibitory activities on the glycolytic enzymes glyceraldehyde-3-phosphate dehydrogenase and triosephosphate isomerase, and were substrates for monoamine oxidase to equivalent extents.