TY - JOUR
T1 - Enantiomeric cannabidiol derivatives
T2 - Synthesis and binding to cannabinoid receptors
AU - Hanuš, Lumír O.
AU - Tchilibon, Susanna
AU - Ponde, Datta E.
AU - Breuer, Aviva
AU - Fride, Ester
AU - Mechoulam, Raphael
PY - 2005/3/21
Y1 - 2005/3/21
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 CB1 and CB2 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 CB1 receptor in the low nanomole range. Some of these compounds also bind weakly to the CB2 receptor.
AB - (-)-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 CB1 and CB2 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 CB1 receptor in the low nanomole range. Some of these compounds also bind weakly to the CB2 receptor.
UR - http://www.scopus.com/inward/record.url?scp=16244383829&partnerID=8YFLogxK
U2 - 10.1039/b416943c
DO - 10.1039/b416943c
M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???
C2 - 15750656
AN - SCOPUS:16244383829
SN - 1477-0520
VL - 3
SP - 1116
EP - 1123
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 6
ER -