1.0 2020-03-19 00:37:20 UTC 2020-11-18 16:35:10 UTC CDB000038 Delta-9-cis-tetrahydrocannabinol Delta-9-cis-tetrahydrocannabinol (Cis-THC) belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Delta-9-cis-tetrahydrocannabinol is the cis isomer of the more abundant, and well known, THC. Delta-9-cis-tetrahydrocannabinol was found as a major contaminant in samples of confiscated marijuana (PMID: 6991645).The actions of THC result from its partial agonist activity at the cannabinoid receptor CB1, located mainly in the central nervous system, and the CB2 receptor, mainly expressed in cells of the immune system (PMID: 17828291). Delta-9-cis-tetrahydrocannabinol is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). C21H30O2 314.47 314.2246 (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol 43009-38-7 CCCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@@H]3C(C)(C)OC2=C1 InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17+/m1/s1 CYQFCXCEBYINGO-SJORKVTESA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle logp 7.29 ALOGPS logs -5.08 ALOGPS logp 5.94 ChemAxon pka_strongest_acidic 9.34 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol ChemAxon average_mass 314.47 ChemAxon mono_mass 314.2246 ChemAxon smiles CCCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@@H]3C(C)(C)OC2=C1 ChemAxon formula C21H30O2 ChemAxon inchi InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17+/m1/s1 ChemAxon inchikey CYQFCXCEBYINGO-SJORKVTESA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 96.73 ChemAxon polarizability 38.77 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 52083428 12831993 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Pertwee RG: The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: delta9-tetrahydrocannabinol, cannabidiol and delta9-tetrahydrocannabivarin. Br J Pharmacol. 2008 Jan;153(2):199-215. doi: 10.1038/sj.bjp.0707442. Epub 2007 Sep 10. 17828291