Tags

Type your tag names separated by a space and hit enter

Enantiomeric cannabidiol derivatives: synthesis and binding to cannabinoid receptors.
Org Biomol Chem 2005; 3(6):1116-23OB

Abstract

(-)-Cannabidiol (CBD) is a major, non psychotropic constituent of cannabis. It has been shown to cause numerous physiological effects of therapeutic importance. We have reported that CBD derivatives in both enantiomeric series are of pharmaceutical interest. Here we describe the syntheses of the major CBD metabolites, (-)-7-hydroxy-CBD and (-)-CBD-7-oic acid and their dimethylheptyl (DMH) homologs, as well as of the corresponding compounds in the enantiomeric (+)-CBD series. The starting materials were the respective CBD enantiomers and their DMH homologs. The binding of these compounds to the CB(1) and CB(2) cannabinoid receptors are compared. Surprisingly, contrary to the compounds in the (-) series, which do not bind to the receptors, most of the derivatives in the (+) series bind to the CB(1) receptor in the low nanomole range. Some of these compounds also bind weakly to the CB(2) receptor.

Authors+Show Affiliations

Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Medical Faculty, The Hebrew University of Jerusalem, Ein Kerem 91120, Jerusalem, Israel. lumir@cc.huji.ac.ilNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15750656

Citation

Hanus, Lumír O., et al. "Enantiomeric Cannabidiol Derivatives: Synthesis and Binding to Cannabinoid Receptors." Organic & Biomolecular Chemistry, vol. 3, no. 6, 2005, pp. 1116-23.
Hanus LO, Tchilibon S, Ponde DE, et al. Enantiomeric cannabidiol derivatives: synthesis and binding to cannabinoid receptors. Org Biomol Chem. 2005;3(6):1116-23.
Hanus, L. O., Tchilibon, S., Ponde, D. E., Breuer, A., Fride, E., & Mechoulam, R. (2005). Enantiomeric cannabidiol derivatives: synthesis and binding to cannabinoid receptors. Organic & Biomolecular Chemistry, 3(6), pp. 1116-23.
Hanus LO, et al. Enantiomeric Cannabidiol Derivatives: Synthesis and Binding to Cannabinoid Receptors. Org Biomol Chem. 2005 Mar 21;3(6):1116-23. PubMed PMID: 15750656.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantiomeric cannabidiol derivatives: synthesis and binding to cannabinoid receptors. AU - Hanus,Lumír O, AU - Tchilibon,Susanna, AU - Ponde,Datta E, AU - Breuer,Aviva, AU - Fride,Ester, AU - Mechoulam,Raphael, Y1 - 2005/02/16/ PY - 2005/3/8/pubmed PY - 2006/6/16/medline PY - 2005/3/8/entrez SP - 1116 EP - 23 JF - Organic & biomolecular chemistry JO - Org. Biomol. Chem. VL - 3 IS - 6 N2 - (-)-Cannabidiol (CBD) is a major, non psychotropic constituent of cannabis. It has been shown to cause numerous physiological effects of therapeutic importance. We have reported that CBD derivatives in both enantiomeric series are of pharmaceutical interest. Here we describe the syntheses of the major CBD metabolites, (-)-7-hydroxy-CBD and (-)-CBD-7-oic acid and their dimethylheptyl (DMH) homologs, as well as of the corresponding compounds in the enantiomeric (+)-CBD series. The starting materials were the respective CBD enantiomers and their DMH homologs. The binding of these compounds to the CB(1) and CB(2) cannabinoid receptors are compared. Surprisingly, contrary to the compounds in the (-) series, which do not bind to the receptors, most of the derivatives in the (+) series bind to the CB(1) receptor in the low nanomole range. Some of these compounds also bind weakly to the CB(2) receptor. SN - 1477-0520 UR - https://www.unboundmedicine.com/medline/citation/15750656/Enantiomeric_cannabidiol_derivatives:_synthesis_and_binding_to_cannabinoid_receptors_ L2 - https://doi.org/10.1039/b416943c DB - PRIME DP - Unbound Medicine ER -