Compound: JWH-133
SMILES: O1c2c(ccc(c2)C(CCC)(C)C)[C@@H]3CC(C)=CC[C@H]3C1(C)C
InChIKey: YSBFLLZNALVODA-RBUKOAKNSA-N
Synonyms: JWH-133, 259869-55-1, JWH 133, JWH133, JW 133, (6AR,10AR)-3-(1,1-DIMETHYLBUTYL)-6A,7,10,10A-TETRAHYDRO-6,6,9-TRIMETHYL-6H-DIBENZO[B,D]PYRAN, 1,1-dimethylbutyl-1-deoxy-Delta(9)-THC, TDG8048RDA, (6aR,10aR)-6,6,9-trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene, CHEBI:146243, DTXSID30426077, (6AR,10AR)-3-(1,1-DIMETHYLBUTYL)-6A,7,10,10A-TETRAHYDRO-6,6,9-TRIMETHYL-6H-DIBENZO(B,D)PYRAN, (6aR,10aR)-6,6,9-trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydrobenzo(c)chromene, RefChem:924023, DTXCID20376911, CHEMBL371214, (6aR,10aR)-6,6,9-trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene, JW 133 (10 mg/mL in Methyl Acetate), 6H-Dibenzo[b,d]pyran, 3-(1,1-dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-, (6aR,10aR)-, YSBFLLZNALVODA-RBUKOAKNSA-N, (6aR,10aR)-3-(1,1-Dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran, , ; JWH 133, 6H-DIBENZO(B,D)PYRAN, 3-(1,1-DIMETHYLBUTYL)-6A,7,10,10A-TETRAHYDRO-6,6,9-TRIMETHYL-, (6AR,10AR)-, UNII-TDG8048RDA, GTPL747, (6aR,10aR)-6,6,9-Trimethyl-3-(2-methyl-2-pentanyl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene, SCHEMBL1517632, SCHEMBL29372663, GLXC-06040, EX-A1014, BDBM50180036, NSC792741, AKOS024456536, CS-5513, NSC-792741, 3-(1,1-dimethylbutyl)-6aR,7,10,10aR-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran, AS-89656, BJ164539, HY-15854, DB-235196, Q6109195, (6aR,10aR)-3-(1,1-Dimethyl-butyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene, (6aR,10aR)-3-(1,1-dimethylbutyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6Hdibenzo[b,d]pyran, (6aR,10aR)-6,6,9-Trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran
Theoretical properties:
molecular_formula: C22H32O
molecular_weight: 312.5 g/mol
exact_mass: 312.245315640 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 3
heavy_atom_count: 23
topological_polar_surface_area: 9.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "JWH-133 is a dibenzopyran that is 9-tetrahydrocannabinol which is lacking the hydroxy group and in which the pentyl group at position 3 has been replaced by a 1,1-dimethylbutyl group. A potent and highly selective CB2 receptor agonist. It has a role as a CB2 receptor agonist, an analgesic, an opioid analgesic, an antineoplastic agent, a vasodilator agent, an anti-inflammatory agent and an apoptosis inhibitor. It is an organic heterotricyclic compound, a benzochromene and a dibenzopyran.", "chebi": "A dibenzopyran that is <a href=\"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66964\" target=\"_blank\">\u0394<small><sup>9</small></sup>-tetrahydrocannabinol</a> which is lacking the hydroxy group and in which the pentyl group at position 3 has been replaced by a 1,1-dimethylbutyl group. A potent and highly selective CB<small><sub>2</sub></small> receptor agonist.", "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "JWH-133 (Dimethylbutyl-deoxy-Delta-8-THC) is a potent selective CB2 receptor agonist with a Ki of 3.4nM and selectivity of around 200x for CB2 over CB1 receptors. It was discovered by and named after John W. Huffman.\nJWH-133 has been confused with other analogs of Delta-8-THC in peer-reviewed literature. It has been confused with Dimethylpentyl-Delta-8-THC as well as Dimethylbutyl-Delta-8-THC, including confusing the chemical name with Dimethylbutyl-Delta-8-THC itself. It has been confused with the Delta-9 isomer  \nThe 3-(1',1'-Dimethylbutyl)-1-deoxy-delta-8-THC is a selective CB2 agonist, binding 677nM at Cb1 and 3.4nM at CB2 while 3-(1',1'-Dimethylbutyl)-delta-8-THC itself binds 65nM at CB1. Structurally the only difference between JWH-133 and dimethylbutyl-D8-THC is that JWH-133 lacks the hydroxy group seen on dimethylbutyl-D8-THCs phenol structure (the C1 position of the A ring), turning this group into a phenyl (JWH-133) instead of phenol. It is generally accepted that removing the hydroxy group from the phenol structure of any classical cannabinoid benzopyran (such as THC) results in dramatically less CB1 activity and heightened CB2 activity.\nJWH-133, alongside WIN 55,212-2 and HU-210, is responsible for preventing the inflammation caused by Amyloid beta proteins involved in Alzheimer's disease, in addition to preventing cognitive impairment and loss of neuronal markers. This anti-inflammatory action is induced through agonist action at the CB2 receptor, which prevents microglial activation that elicits the inflammation. Additionally, cannabinoids at this receptor completely abolish neurotoxicity related to microglia activation in rat models.\nIt may be linked with anti-cancer properties, according to pre-trial data from a 2010 study in Madrid."}