ortho-Chlorobenzylmalononitrile: A metabolite formed from ortho-chlorobenzylidenemalononitrile (CS)

Abstract

ortho-Chlorobenzylamalononitrile (CSH2) has been identified by mass spectrometry as a metabolite of ortho-chlorobenzylidenemalononitrile (CS). The reduction of the benzylidene double bond in CS decreases its toxicity: the LD50 (iv) of CSH2 in mice is 78.4 mg/kg, higher than that of CS, and the irritancy of CSH2, measured in the guinea pig blepharospasm test, is 15 times less than that of CS. Evidence is presented which suggests that the reduction of CS to CSH2 in blood is catalyzed by an enzyme in the erythrocyte cytoplasm and that NADPH is a specific coenzyme. © 1973.