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CAY10429
Cayman Chemical Item Number 10004259
Description
Traditionally, the activity of cannabinoid (CB) agonists was thought to be transduced by a pair of G protein-coupled receptors, CB1 and CB2.1↗ CAY10429 (abnormal cannabidiol) is a synthetic regioisomer of cannabidiol that fails to elicit either CB1 or CB2 responsiveness and is without psychotropic activity. CAY10429 induces endothelium-dependent vasodilation via a CB1/CB2/NO-independent mechanism.2↗ At a dose of 20 µg/g in rats, CAY10429 showed hypotensive activity that could not be antagonized by cannabidiol or SR141716A. CAY10429 is therefore believed to activate a third type of CB receptor, provisionally called the non-CB1/CB2 endocannabinoid receptor. CAY10429 also acts via these receptors to regulate the migratory activity of murine BV-2 microglial cells, with an EC50 of 600 nM.3↗
1 Felder, C.C., Joyce, K.E., Briley, E.M., et al. Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol Pharmacol 48 443-450 (1995).
2 Járai, Z., Wagner, J.A., Varga, K., et al. Cannabinoid-induced mesenteric vasodilation through an endothelial site distinct from CB1 or CB2 receptors. Proc Natl Acad Sci USA 96(24) 14136-14141 (1999).
3 Walter, L., Franklin, A., Witting, A., et al. Nonpsychotropic cannabinoid receptors regulate microglial cell migration. J Neurosci 23(4) 1398-1405 (2003).
Synonyms Abn-CBD
Abnormal Cannabidiol
Formal Name 4-[3-methyl-6R-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol
CAS Number 22972-55-0
Molecular Formula C21H30O2
Formula Weight 314.5
Formulation A solution in methyl acetate
Purity >98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES Copy CC1=C[C@@H](C2=C(CCCCC)C=C(O)C=C2O)[C@H](C(C)=C)CC1
InCHI Code Copy 1S/C21H30O2/c1-5-6-7-8-16-12-17(22)13-20(23)21(16)19-11-15(4)9-10-18(19)14(2)3/h11-13,18-19,22-23H,2,5-10H2,1,3-4H3/t18-,19+/m0/s1
InCHI Key Copy YWEZXUNAYVCODW-RBUKOAKNSA-N |