Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
3
pubmed:dateCreated
1992-5-14
pubmed:abstractText
Numerous cannabinoids have been synthesized that are extremely potent in all of the behavioral assays conducted in our laboratory. An important feature in increasing potency has been the substitution of a dimethylheptyl (DMH) side chain for the pentyl side chain. Our previous studies have shown that (-)-11-OH-delta 8-THC-dimethylheptyl was 80-1150 times more potent than delta 9-THC. Stereospecificity was demonstrated by its (+)-enantiomer which was more than 1400-7500 times less potent. A related series of DMH cannabinoid analogs has recently been synthesized and preliminary evaluations reported here. (-)-11-OH-delta 9-THC-DMH was found to be equipotent with (-)-11-OH-delta 8-THC-DMH. The aldehyde (-)-11-oxo-delta 9-THC-DMH was 15-50 times more potent than delta 9-THC. Surprisingly, (-)-11-carboxy-delta 9-THC-DMH was also active, being slightly more potent than delta 9-THC. In the bicyclic cannabinoid series, the length and bulk of the side chain were found to be equally important. Aminoalkylindoles, which are structurally dissimilar from classical cannabinoids, have been found to exhibit a pharmacological profile similar to delta 9-THC. Though not extremely potent in vivo, they appear to represent an entirely new approach to studying the actions of the cannabinoids. The structural diversity and wide-ranging potencies of the analogs described herein provide the opportunity to develop a pharmacophore for the cannabinoids using molecular modeling techniques.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Nov
pubmed:issn
0091-3057
pubmed:author
pubmed:issnType
Print
pubmed:volume
40
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
471-8
pubmed:dateRevised
2007-11-15
pubmed:meshHeading
pubmed-meshheading:1666911-Analgesics, pubmed-meshheading:1666911-Animals, pubmed-meshheading:1666911-Behavior, Animal, pubmed-meshheading:1666911-Benzoxazines, pubmed-meshheading:1666911-Body Temperature, pubmed-meshheading:1666911-Brain, pubmed-meshheading:1666911-Cannabinoids, pubmed-meshheading:1666911-Cyclohexanols, pubmed-meshheading:1666911-Male, pubmed-meshheading:1666911-Mice, pubmed-meshheading:1666911-Mice, Inbred ICR, pubmed-meshheading:1666911-Models, Molecular, pubmed-meshheading:1666911-Molecular Conformation, pubmed-meshheading:1666911-Morpholines, pubmed-meshheading:1666911-Motor Activity, pubmed-meshheading:1666911-Naphthalenes, pubmed-meshheading:1666911-Rats, pubmed-meshheading:1666911-Rats, Inbred Strains, pubmed-meshheading:1666911-Receptors, Drug, pubmed-meshheading:1666911-Structure-Activity Relationship, pubmed-meshheading:1666911-Tetrahydrocannabinol
pubmed:year
1991
pubmed:articleTitle
Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs.
pubmed:affiliation
Department of Pharmacology and Toxicology, Virginia Commonwealth University, Richmond 23298.
pubmed:publicationType
Journal Article, In Vitro, Research Support, U.S. Gov't, P.H.S., Research Support, Non-U.S. Gov't