JWH-133 show (6aR,10aR)-3-(1,1-Dimethylbutyl)-6a,7,10,10a-tetrahydro -6,6,9-trimethyl-6H-dibenzo[b,d]pyran
CAS Number PubChem CID IUPHAR/BPS ChemSpider UNII ChEBI ChEMBL CompTox Dashboard (EPA ) Formula C 22 H 32 O Molar mass −1 3D model (JSmol ) show O3c1cc(ccc1[C@@H]2C\C(=C/C[C@H]2C3(C)C)C)C(C)(C)CCC
show 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 N Y (what is this?)
JWH-133 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, 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 .[1]
Legal Status [ ] As the U.S. Drug Enforcement Administration criminalizes any extract "containing one or more cannabinoids," JWH-133 is a scheduled substance in the U.S.[2] JWH-018 , as JWH-133 is selective for the non-psychoactive CB2 receptor and thus lacks significant psychoactive effects .
References [ ]
^ Caffarel MM, Andradas C, Mira E, Pérez-Gómez E, Cerutti C, Moreno-Bueno G, Flores JM, García-Real I, Palacios J, Mañes S, Guzmán M, Sánchez C (July 2010). "Cannabinoids reduce ErbB2-driven breast cancer progression through Akt inhibition" . Molecular Cancer . 9 : 196. doi :10.1186/1476-4598-9-196 . PMC 2917429 PMID 20649976 . Lay summary – NORML . ^ "PART 1308 - Section 1308.11 Schedule I" . www.deadiversion.usdoj.gov . Retrieved 2020-01-08 .
Further reading [ ] show Cannabinoids
Phytocannabinoids
Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabinols and cannabinodiols Cannabitriols Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols
Delta-9-THC (THC)
THCP
THCV
Miscellaneous cannabinoids
Caryophyllene Alkylamides Epigallocatechin gallate Gallocatechol Perrottetinene Serinolamide A Yangonin Active metabolites
Endocannabinoids
Arachidonoyl ethanolamide (AEA; anandamide) 2-Arachidonoylglycerol (2-AG) 2-Arachidonyl glyceryl ether (2-AGE; noladin ether) 2-Oleoylglycerol (2-OG) N-Arachidonoyl dopamine (NADA) N-Arachidonylglycine (NAGly) N-Arachidonoyl serotonin (AA-5-HT) Docosatetraenoylethanolamide (DEA) Lysophosphatidylinositol (LPI) Oleamide Oleoylethanolamide (OEA) Palmitoylethanolamide (PEA) RVD-Hpα Stearoylethanolamide (SEA) O-Arachidonoyl ethanolamine (O-AEA; virodhamine) Synthetic
Classical cannabinoids Non-classical Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols Eicosanoids Hydrocarbons Indazole carboxamides Indazole-3- Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes
AM-2201 AM-694 WIN-55,212-2 Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- Tetramethylcyclo-
A-796,260 A-834,735 FUB-144 UR-144 XLR-11 XLR-12 Tetramethylcyclo- Others
Allosteric CBR ligands Endocannabinoid (inactivation inhibitors) Anticannabinoids (antagonists/inverse
See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)List of: AM cannabinoids JWH cannabinoids Designer drugs § Synthetic cannabimimetics
show Receptor (ligands )
CB1
Agonists (abridged; see here for more) : 2-AG 2-AGE (noladin ether) 11-Hydroxy-THC α-Amyrin · β-Amyrin AB-CHMINACA AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 Anandamide AZ-11713908 Cannabinol CB-13 CP 47,497 CP 55,940 Dimethylheptylpyran DEA ECG EGCG Epicatechin Gallocatechol (gallocatechin) Honokiol HU-210 JWH-007 JWH-015 JWH-018 JWH-073 Kavain L-759,633 Levonantradol Menabitan Nabilone Nabitan NADA O-1812 Oleamide Pravadoline Serinolamide A THC (dronabinol) UR-144 WIN 55,212-2 Yangonin CB2
Agonists: 2-AG 2-AGE (noladin ether) 3,3'-Diindolylmethane 4-O-Methylhonokiol α-Amyrin · β-Amyrin A-796,260 A-834,735 A-836,339 AM-1221 AM-1235 AM-1241 AM-2232 Anandamide AZ-11713908 Cannabinol Caryophyllene CB-13 CBS-0550 CP 55,940 GW-405,833 (L-768,242) GW-842,166X HU-308 JTE 7-31 JWH-007 JWH-015 JWH-018 JWH-133 L-759,633 L-759,656 Magnolol MDA-19 Nabitan NADA Olorinab (APD-371) PF-03550096 S-444,823 SER-601 Serinolamide A UR-144 Tedalinab THC (dronabinol) THCV Virodhamine NAGly GPR18 )
Agonists: Abnormal cannabidiol ACPA AM251 Anandamide Cannabidiol NADGly THC (dronabinol) O-1602 GPR55
Agonists: 2-AGE (noladin ether) Abnormal cannabidiol AM-251 CP 55,940 Lysophosphatidylinositol O-1602 Oleoylethanolamide Palmitoylethanolamide THC (dronabinol) GPR119 Unsorted
Transporter (modulators )
eCBTs
Inhibitors: AM-404 Arachidonoyl serotonin Cannabidiol Guineensine LY-2183240 Paracetamol (acetaminophen) URB-597 VDM-11
Enzyme (modulators )
FAAH MAGL
Inhibitors: IDFP JZL-184 JZL-195 MAFP URB-602 ABHD6 ABHD12
Inhibitors: Betulinic acid Maslinic acid MAFP Oleanolic acid Orlistat (tetrahydrolipstatin) Ursolic acid
Others
Precursors: Phosphatidylethanolamine NAPE Diacylglycerol Others: (directly potentiates activity of 2-AG at CB1 receptor) (FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators Cannabinoids (cannabinoids by structure)
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