Racemation of the benzodiazepines camazepam and ketazolam and receptor binding of enantiomers].

The chiral benzodiazepines camazepam (1) and ketazolam (2) were resolved into the enantiomers by chromatography on the optically active adsorbent poly[(S)-N-(1-cyclohexylethyl)-methacrylamide] and fractional crystallisation or repeated chromatography, respectively. The IC50 values of the isomers and of the racemates of both compounds were determined by displacement of radioactively labelled 3H-flunitrazepam and 3H-propyl-beta-carboline-carboxylate from their specific binding sites. (+)-Camazepam exhibits 14fold higher affinity compared to the (-)-enantiomer. In contrast only slight differences in the receptor affinity are observed with the ketazolam enantiomers.

Citation

G Blaschke, H Kley, W E Müller. Racemation of the benzodiazepines camazepam and ketazolam and receptor binding of enantiomers]. Arzneimittel-Forschung. 1986 Jun;36(6):893-4

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PMID: 2874815

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