ABSTRACT
The axial and equatorial isomers of 7-(methylamino)hexahydrocannabinol (1 and 2) and 7-(dimethylamino)hexahydrocannabinol (3 and 4) were prepared by reductive amination of the corresponding cannabinoid aldehydes. The amines caused some tranquility in baboons but did not evoke the typical cannabimimetic syndrome caused by psychoactive cannabinoids. However the axial amines (1 and 3) but not the equatorial ones (2 and 4) caused bouts of scratching and yawning. The latter is a rare pharmacological effect hitherto not observed with other cannabinoids.
Subject(s)
Cannabinoids/chemical synthesis , Stereotyped Behavior/drug effects , Animals , Cannabinoids/pharmacology , Chemical Phenomena , Chemistry , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Conformation , Optical Rotation , Papio , Spectrophotometry, Infrared , Structure-Activity RelationshipABSTRACT
Several pairs of cannabinoid isomers were synthesized and tested for psychotropic activity in rhesus monkeys. Two regularities were observed: (a) In the absence of the other substituents, the equatorial stereochemistry of the substituent at C-1 determines activity. (b) Two groups of THC-type cannabinoids which differ only in that the chemical groupings in one of them at C-1, C-2 are situated at C-1, C-6 in the other (but retain their stereochemistry) have almost equivalent psychotropic activity.
Subject(s)
Cannabinoids/pharmacology , Animals , Cannabinoids/chemical synthesis , Macaca mulatta , Molecular Conformation , Psychotropic Drugs/chemical synthesis , Stereoisomerism , Structure-Activity RelationshipABSTRACT
In attempt to improve distribution and transport qualities of antidotes against organophosphorus poisoning, a new series of pyridine aldoximes linked to glucose moiety were synthesized and studied both in vivo and in vitro. Preliminary results describing the biological activity of the new compounds are presented and discussed in this report.
Subject(s)
Antidotes/chemical synthesis , Glucose/analogs & derivatives , Organophosphate Poisoning , Pralidoxime Compounds/chemical synthesis , Animals , Cholinesterase Reactivators/chemical synthesis , Cholinesterase Reactivators/pharmacology , Cholinesterases/metabolism , Eels , Glucose/chemical synthesis , Glucose/pharmacology , Mice , Pralidoxime Compounds/pharmacologySubject(s)
Cannabis/pharmacology , Structure-Activity Relationship , Alkylation , Animals , Behavior, Animal/drug effects , Chemical Phenomena , Chemistry , Cyclization , Dogs , Dronabinol/chemical synthesis , Dronabinol/pharmacology , Female , Haplorhini , Macaca , Male , Motor Activity/drug effects , Phenols , Pyrans , RadiochemistryABSTRACT
6beta-Hydroxy-delta(1)-tetrahydrocannabinol, a metabolite of delta(1)-tetrahydrocannabinol has been synthesized from delta(6)-tetrahydrocannabinol. It shows high tetrahydrocannabinol-type activity in rhesus monkeys. The implications of this funding are discussed.
