Cannabidiol-dimethylheptyl (CBD-DMH orDMH-CBD) is a synthetichomologue ofcannabidiol where the pentyl chain has been replaced by a dimethylheptyl chain. Severalisomers of this compound are known. The most commonly used isomer in research is (−)-CBD-DMH, which has the samestereochemistry as natural cannabidiol, and a 1,1-dimethylheptyl side chain. This compound is not psychoactive and acts primarily as ananandamidereuptake inhibitor, but is more potent than cannabidiol as ananticonvulsant and has around the same potency as anantiinflammatory.[1][2][3][4] Unexpectedly the “unnatural”enantiomer (+)-CBD-DMH, which has reversed stereochemistry from cannabidiol, was found to be a directly acting cannabinoid receptor agonist with aKi of 17.4nM at CB1 and 211nM at CB2, and produces typical cannabinoid effects in animal studies,[5] as does its 7-OH derivative.[6]
(−)-CBD-DMH (left) and (+)-CBD-DMH (right)7-OH-(+)-CBD-DMH
Another closely analogous compound has also been described, with the double bond in thecyclohexene ring shifted to between the 1,6-positions rather than the 2,3-positions (i.e. analogous to syntheticTHC analogues such asparahexyl), the isopropenyl group saturated to isopropyl, and a 1,2-dimethylheptyl side chain. It is synthesized byBirch reduction from the 1,2-dimethylheptyl analogue ofcannabidiol. This compound also produces potent cannabinoid-like effects in animals, but has three chiral centers and is composed of a mixture of eightstereoisomers, which have not been studied individually, so it is not known which stereoisomers are active.[7][8]
^Leite JR, Carlini EA, Lander N, Mechoulam R (1982). "Anticonvulsant effects of the (-) and (+)isomers of cannabidiol and their dimethylheptyl homologs".Pharmacology.24 (3):141–6.doi:10.1159/000137588.PMID7071126.
^Ben-Shabat S, Hanus LO, Katzavian G, Gallily R (February 2006). "New cannabidiol derivatives: synthesis, binding to cannabinoid receptor, and evaluation of their antiinflammatory activity".Journal of Medicinal Chemistry.49 (3):1113–7.doi:10.1021/jm050709m.PMID16451075.
^Hanus LO, Tchilibon S, Ponde DE, Breuer A, Fride E, Mechoulam R (March 2005). "Enantiomeric cannabidiol derivatives: synthesis and binding to cannabinoid receptors".Organic & Biomolecular Chemistry.3 (6):1116–23.doi:10.1039/B416943C.PMID15750656.
^Fride E, Ponde D, Breuer A, Hanus L (June 2005). "Peripheral, but not central effects of cannabidiol derivatives: mediation by CB(1) and unidentified receptors".Neuropharmacology.48 (8):1117–29.doi:10.1016/j.neuropharm.2005.01.023.PMID15910887.S2CID16531395.
^Razdan RK, Pars HG, Thompson WR, Granchelli FE (1974). "Lithium-ammonia reduction of tetrahydrocannabinols".Tetrahedron Letters.15 (49–50):4315–4318.doi:10.1016/S0040-4039(01)92152-5.
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