William A. Day

Cannabinoids. 3. Synthetic approaches to 9-ketocannabinoids. Total synthesis of nabilone.

Aufgrund des klinischen Interesses von Nabilon (VIa) werden verschiedene Synthesen zur Herstellung dieser Verbindung beschrieben, die an bekannte Verfahren anschliesen.

Comparison of the oxime and the hydroxylamine derivatives of 4-chloroamphetamine as depletors of brain 5-hydroxyindoles

Brain 5-hydroxyindole levels were measured 6 hr after the i.p. injection of 4-chloroamphetamine and two of its possible metabolites—the oxime and the hydroxylamine. Both 4-chloroamphetamine and N-hydroxy-4-chloroamphetamine at 0·1 m-mole/kg caused marked reduction of serotonin and of 5-hydroxyindoleacetic acid levels, whereas the oxime had only a slight effect on serotonin levels. The N-hydroxy derivative appeared to be almost completely reduced to 4-chloroamphetamine in vivo, for it produced brain levels of 4-chloroamphetamine equivalent to those produced by 4-chloroamphetamine itself and lowered brain 5-hydroxyindole levels as much as did 4-chloroamphetamine at three different dose levels. Our results make it seem unlikely that 4-chloroamphetamines depletion of brain serotonin and 5-hydroxyindoleacetic acid is mediated by the conversion of 4-chloroamphetamine to these metabolites.