title: The use of proton nuclear magnetic resonance spectrometry (1H NMR) for monitoring the reaction of epoxides with butylamine and predictive capabilities of the relative alkylation index (RAI) for skin sensitization by epoxides.
abstract: A group of alkyl epoxides was compared for their guinea pig sensitization capacity and reactivities towards a protein-surrogate substrate, n-butylamine. Instead of the previously reported use of a titration method for determination of alkylation rate, proton nuclear magnetic resonance spectrometry (1H NMR) was used. The resulting relative alkylation indices (RAIs) were calculated in order to correlate these indices with the results of the guinea pig sensitization test data. The use of 1H NMR was determined to be a useful tool for collection of in vitro reaction rates, but there was no correlation between the RAIs and guinea pig sensitization score for this group of epoxides.
authors.affiliation: Dow Chemical Company, Freeport, Texas 77541.
authors.forename: J E
authors.initials: JE
authors.lastname: Betso
authors.forename: R E
authors.initials: RE
authors.lastname: Carreon
authors.forename: V M
authors.initials: VM
authors.lastname: Miner
mesh_terms: D000478:Alkylation; D000818:Animals; D002082:Butylamines / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry / Q000633:toxicity*; D006168:Guinea Pigs; D009682:Magnetic Resonance Spectroscopy; D011237:Predictive Value of Tests; D011522:Protons; D012867:Skin / Q000187:drug effects*
chemical_list: D002082:Butylamines; D004852:Epoxy Compounds; D011522:Protons