Contents

JWH-133

Chemical compound

JWH-133

Identifiers
IUPAC name (6aR,10aR)-3-(1,1-Dimethylbutyl)-6a,7,10,10a-tetrahydro -6,6,9-trimethyl-6H-dibenzo[b,d]pyran
CAS Number	259869-55-1 N
PubChem CID	6918505
IUPHAR/BPS	747
ChemSpider	5293702 Y
UNII	TDG8048RDA
ChEBI	CHEBI:146243
ChEMBL	ChEMBL371214 Y
CompTox Dashboard (EPA)	DTXSID30426077
Chemical and physical data
Formula	C22H32O
Molar mass	312.497 g·mol−1
3D model (JSmol)	Interactive image
SMILES O3c1cc(ccc1[C@@H]2C\C(=C/C[C@H]2C3(C)C)C)C(C)(C)CCC
InChI InChI=1S/C22H32O/c1-7-12-21(3,4)16-9-10-17-18-13-15(2)8-11-19(18)22(5,6)23-20(17)14-16/h8-10,14,18-19H,7,11-13H2,1-6H3/t18-,19+/m0/s1 Y Key:YSBFLLZNALVODA-RBUKOAKNSA-N Y
NY (what is this?)  (verify)

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.

JWH-133 has been confused with other analogs of Delta-8-THCinpeer-reviewed literature. It has been confused with Dimethylpentyl-Delta-8-THC as well as Dimethylbutyl-Delta-8-THC,^[1] including confusing the chemical name with Dimethylbutyl-Delta-8-THC itself. It has been confused with the Delta-9 isomer^[2]

The 3-(1',1'-Dimethylbutyl)-1-deoxy-delta-8-THC is a selective CB2 agonist, binding 677nM at Cb1 and 3.4nM at CB2^[3] while 3-(1',1'-Dimethylbutyl)-delta-8-THC itself binds 65nM at CB1.^[4] 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.^[4][3] It's 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.^{[citation needed]}

JWH-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.^{[citation needed]} 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.^{[citation needed]}

It may be linked with anti-cancer properties, according to pre-trial data from a 2010 study in Madrid.^[5]

Legal Status[edit]

JWH-133 is not specifically listed in the United States controlled substance act but may be considered an analog of THC (under the Federal Analogue Act) if sold for human consumption.^[6]

References[edit]

Further reading[edit]