Drugs derived from cannabinoids. 2. Basic esters of nitrogen and carbocyclic analogs

Various basic esters of nitrogen (2) and carbocyclic (3 and 4) analogs of cannabinoids were synthesized using dicyclohexylcarbodiimide in methylene chloride. The compounds in the three series werw studied in selected pharmacological tests in mice, rats, dogs, and cats. It was shown that making the b...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1976-04, Vol.19 (4), p.454-461
Main Authors: Razdan, Raj K, Zitko Terris, B, Pars, Harry G, Plotnikoff, Nicholas P, Dodge, Patrick W, Dren, Anthony T, Kyncl, Jaroslav, Somani, Peter
Format: Article
Language:English
Subjects:
Acoustic Stimulation
Aggression - drug effects
Analgesics
Animals
Ataxia - chemically induced
Behavior, Animal - drug effects
Cannabis - chemical synthesis
Cats
Dihydroxyphenylalanine - pharmacology
Dogs
Dronabinol - analogs & derivatives
Dronabinol - chemical synthesis
Dronabinol - pharmacology
Dronabinol - toxicity
Esters
Haplorhini
Humans
Hypnotics and Sedatives
Lethal Dose 50
Male
Mice
Motor Activity - drug effects
Phytotherapy
Rats
Reaction Time - drug effects
Seizures - etiology
Sleep - drug effects
Structure-Activity Relationship
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Summary:Various basic esters of nitrogen (2) and carbocyclic (3 and 4) analogs of cannabinoids were synthesized using dicyclohexylcarbodiimide in methylene chloride. The compounds in the three series werw studied in selected pharmacological tests in mice, rats, dogs, and cats. It was shown that making the basic ester from the phenol retains biological activity and can lead to a greater selectivity of action, particularly the antinociceptive activity. The most interesting esters were 5, 6, 10, and 14 in the nitrogen analogs series and 19 and 20 in the carbocyclic series. Compound 5 was more potent than codeine in the writhing, hot-plate, and tail-flick tests and is at present undergoing clinical testing. Compound 20 was very potent in the mouse audiogenic seizure test and is of interest as an anticovulsant agent.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00226a002