Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase.

Content Provider	Semantic Scholar
Author	Rhee, Meung Ho Vogel, Zvi Barg, J. Bayewitch, Michael Levy, Rivka Hanuš, Lumír Ondřej Breuer, Aviva Mechoulam, Raphael
Copyright Year	1997
Abstract	Several derivatives of cannabinol and the 1,1-dimethylheptyl homolog (DMH) of cannabinol were prepared and assayed for binding to the brain and the peripheral cannabinoid receptors (CB1 and CB2), as well as for activation of CB1- and CB2-mediated inhibition of adenylylcyclase. The DMH derivatives were much more potent than the pentyl (i.e., cannabinol) derivatives. 11-Hydroxycannabinol (4a) was found to bind potently to both CB1 and CB2 (Ki values of 38.0 +/- 7.2 and 26.6 +/- 5.5 nM, respectively) and to inhibit CB1-mediated adenylylcyclase with an EC50 of 58.1 +/- 6.2 nM but to cause only 20% inhibition of CB2-mediated adenylylcyclase at 10 microM. It behaves as a specific, though not potent, CB2 antagonist. 11-Hydroxycannabinol-DMH (4b) is a very potent agonist for both CB1 and CB2 (Ki values of 100 +/- 50 and 200 +/- 40 pM; EC50 of adenylylcyclase inhibition 56.2 +/- 4.2 and 207.5 +/- 27.8 pM, respectively).
File Format	PDF HTM / HTML
DOI	10.1021/jm970126f
PubMed reference number	9379442
Journal	Medline
Volume Number	40
Issue Number	20
Alternate Webpage(s)	https://1d7u564dod7i2q96m533sblk-wpengine.netdna-ssl.com/wp-content/uploads/2018/09/Cannabinol-Derivatives-Binding-to-Cannabinoid-Receptors-and-Inhibition-of-Adenylylcyclase.pdf
Alternate Webpage(s)	http://www.weizmann.ac.il/neurobiology/labs/vogel/PDFs/97JMC40-3228.pdf
Alternate Webpage(s)	https://doi.org/10.1021/jm970126f
Journal	Journal of medicinal chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article