Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis and Pharmacological Effects in Mice of Halogenated Cannabinol Derivatives
Hisatoshi YOSHIDANoriyuki USAMIYasumasa OHISHIKazuhito WATANABEIkuo YAMAMOTOHidetoshi YOSHIMURA
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1995 Volume 43 Issue 2 Pages 335-337

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Abstract

Eight halogenated drivatives of cannabinol (CBN) substituted on the aromatic ring at the 2 and/or 4 position were synthesized and their pharmacological effects were evaluated by intracerebroventricular injection (50 μg/mouse)in mice, using hypothermia, pentobarbital-induced sleep prolongation, catalepsy and anticonvulsant effect as indices.The hypothermic effects of monohalogenated drivatives of CBN were comparable to that of CBN, whereas the effects of dihalogenated derivatives of CBN except for the fluorinated derivative were attenuated. In the interaction with pentobarbital, two monochlorinated derivatives exhibited a significant prolongation of sleeping time, although other derivatives did not significantly affect the sleeping time. The cataleptogenic effects of monofluoro- and 4-bromo-CBN were stronger than that of CBN. 4-Bromo-CBN exhibited a significant prolongation of seizure latency induced by pentylenetetrazol. These data suggest that halogenation of CBN modifies the pharmacological profile of the cannabinoid.

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