JWH-133

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-THC in peer-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 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. 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. 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|reason=This is a p It may be linked with anti-cancer properties, according to pre-trial data from a 2010 study in Madrid.[5]

## Legal Status

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]

It is also not specifically listed in the German BtMG.[7]

## References

1. ↑ "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry 8: 17–39. 28 June 2016. doi:10.4137/PMC.S32171. PMID 27398024.
2. ↑ "(6AR,10AR)-3-(1,1-Dimethylbutyl)-6A,7,10,10A-tetrahydro-6,6,9-trimethyl-6H-dibenzo[B,D]pyran". https://pubchem.ncbi.nlm.nih.gov/compound/jwh-133.
3. ↑ 3.0 3.1 "3-(1',1'-Dimethylbutyl)-1-deoxy-delta8-THC and related compounds: synthesis of selective ligands for the CB2 receptor". Bioorganic & Medicinal Chemistry 7 (12): 2905–2914. December 1999. doi:10.1016/S0968-0896(99)00219-9. PMID 10658595.
4. ↑ 4.0 4.1 "Structure-activity relationships for 1',1'-dimethylalkyl-Delta8-tetrahydrocannabinols". Bioorganic & Medicinal Chemistry 11 (7): 1397–1410. April 2003. doi:10.1016/s0968-0896(02)00649-1. PMID 12628666.
5. ↑ "Cannabinoids reduce ErbB2-driven breast cancer progression through Akt inhibition". Molecular Cancer 9 (1): 196. July 2010. doi:10.1186/1476-4598-9-196. PMID 20649976.
* "Marijuana Compound Halts Breast Cancer Tumor Growth". August 5, 2010. https://norml.org/news/2010/08/05/marijuana-compound-halts-breast-cancer-tumor-growth/.
6. ↑ "Federal Register :: Request Access". https://www.ecfr.gov/current/title-21/chapter-II/part-1308.
7. ↑ "Stoffe gem. Anlagen zum BtMG". https://www.bfarm.de/SharedDocs/Downloads/DE/Bundesopiumstelle/Betaeubungsmittel/BtM-Stoffe.xls?__blob=publicationFile.

## Further reading

* "Prevention of Alzheimer's disease pathology by cannabinoids: neuroprotection mediated by blockade of microglial activation". The Journal of Neuroscience 25 (8): 1904–1913. February 2005. doi:10.1523/JNEUROSCI.4540-04.2005. PMID 15728830.

* v
* t
* e

Cannabinoids

Phytocannabinoids|

* Alkylamides
* Caryophyllene
* CBC
* CBCV
* CBD
* CBDV
* CBG
* CBGM
* CBGV
* CBL
* CBDL
* CBN
* CBV
* Epigallocatechin gallate
* Gallocatechol
* Perrottetinene
* Serinolamide A
* THC
* THC-C4
* THCA
* THCV
* Yangonin

* Active metabolites: 8,11-DiOH-THC
* 11-COOH-THC
* 11-OH-THC

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)
* 2-Arachidonoyl lysophosphatidylinositol (2-ALPI)
* 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
cannabinoids|

| Classical cannabinoids
(dibenzopyrans)|

* A-40174
* A-41988
* A-42574
* Ajulemic acid
* AM-087
* AM-411
* AM-855
* AM-905
* AM-906
* AM-919
* AM-926
* AM-938
* AM-2389
* AM-4030
* AMG-1
* AMG-3
* AMG-36
* AMG-41
* Dexanabinol (HU-211)
* DMHP
* Dronabinol
* HHC
* HU-210
* HU-243
* JWH-051
* JWH-133
* JWH-139
* JWH-161
* JWH-229
* JWH-359
* KM-233
* L-759,633
* L-759,656
* Levonantradol (CP 50,5561)
* Menabitan
* Nabazenil
* Nabidrox (Canbisol)
* Nabilone
* Nabitan
* Naboctate
* O-224
* O-581
* O-774
* O-806
* O-823
* O-1057
* O-1125
* O-1191
* O-1238
* O-2048
* O-2113
* O-2365
* O-2372
* O-2373
* O-2383
* O-2426
* O-2484
* O-2545
* O-2694
* O-2715
* O-2716
* O-3223
* O-3226
* Parahexyl
* Pirnabine
* THC-O-acetate
* THC-O-phosphate

|

Non-classical
cannabinoids|

* Cannabicyclohexanol
* CBD-DMH
* CP 47,497
* (C6)-CP 47,497
* (C9)-CP 47,497
* CP 55,244
* CP 55,940
* HU-308
* HU-320
* HU-331
* HU-336
* HU-345
* HU-446
* HU-465
* HU-910
* HUF-101
* Nonabine
* O-1376
* O-1422
* O-1601
* O-1656
* O-1657
* O-1660
* O-1663
* O-1871
* SPA-229
* Tinabinol

Benzoylindoles|

* 1-Butyl-3-(2-methoxybenzoyl)indole
* 1-Butyl-3-(4-methoxybenzoyl)indole
* 1-Pentyl-3-(2-methoxybenzoyl)indole
* AM-630
* AM-679
* AM-694
* AM-1241
* AM-2233
* GW-405,833 (L-768,242)
* Pravadoline
* RCS-4
* WIN 54,461

Naphthoylindoles|

* AM-1220
* AM-1221
* AM-1235
* AM-2201
* AM-2232
* CHM-081
* EAM-2201
* FUB-JWH-018
* JWH-007
* JWH-015
* JWH-018
* JWH-019
* JWH-073
* JWH-081
* JWH-098
* JWH-116
* JWH-122
* JWH-149
* JWH-164
* JWH-182
* JWH-193
* JWH-198
* JWH-200
* JWH-210
* JWH-398
* JWH-424
* MAM-1220
* MAM-2201
* NE-CHMIMO

Naphthoylindazoles|

* THJ-018
* THJ-2201

Pyrrolobenzoxazines|

* WIN 55,212-2

Naphthylmethylindoles|

* JWH-175
* JWH-176
* JWH-184
* JWH-185
* JWH-192
* JWH-194
* JWH-195
* JWH-196
* JWH-197
* JWH-199

Phenylacetylindoles|

* Cannabipiperidiethanone
* JWH-167
* JWH-203
* JWH-249
* JWH-250
* JWH-251
* JWH-302
* RCS-8

Indole-3-carboxamides|

* 5F-ADBICA
* 5F-MDMB-PICA
* 5F-NNE1
* 5F-PCN
* 5F-SDB-006
* AB-FUBICA
* AB-PICA
* ADBICA
* ADB-FUBICA
* APICA
* CUMYL-BICA
* CUMYL-PICA
* CUMYL-5F-PICA
* FDU-NNE1
* MDMB-CHMICA
* MMB-CHMICA
* MMB-2201
* MN-25 (UR-12)
* NNE1
* PX-1
* Org 28312
* Org 28611
* SDB-006
* STS-135

Indole-3-carboxylates|

* 5F-PB-22
* FDU-PB-22
* FUB-PB-22
* QUCHIC (BB-22)
* QUPIC (PB-22)
* NM-2201

Tetramethylcyclo-
propanoylindoles|

* 5Br-UR-144
* 5Cl-UR-144
* A-796,260
* A-834,735
* FUB-144
* UR-144
* XLR-11
* XLR-12

Indazole-3-
carboxamides|

* 4F-MDMB-BINACA
* 5Cl-APINACA
* 5F-ADB
* 5F-ADB-PINACA
* 5F-AMB
* 5F-APINACA
* 5F-CUMYL-PINACA
* 5F-EDMB-PINACA
* 5F-EMB-PINACA
* AB-CHMINACA
* AB-FUBINACA
* AB-FUBINACA 2-fluorobenzyl isomer
* AB-PINACA
* ADB-CHMINACA
* ADB-FUBINACA
* ADB-PINACA
* Adamantyl-THPINACA
* ADSB-FUB-187
* AMB-CHMINACA
* AMB-FUBINACA
* APINACA (AKB48)
* APP-FUBINACA
* CUMYL-4CN-BINACA
* CUMYL-PINACA
* CUMYL-THPINACA
* EMB-FUBINACA
* FUB-APINACA
* MDMB-4en-PINACA
* MDMB-FUBINACA
* MDMB-CHMINACA
* MN-18
* PX-2
* PX-3

Tetramethylcyclo-
propanoylindazoles|

* FAB-144

Naphthoylpyrroles|

* JWH-030
* JWH-147
* JWH-307
* JWH-369
* JWH-370

Eicosanoids|

* AM-883
* AM-1346
* ACEA
* ACPA
* Methanandamide (AM-356)
* O-585
* O-689
* O-1812
* O-1860
* O-1861

Pyrazolecarboxamides|

* 5F-AB-FUPPYCA
* AB-CHFUPYCA

Others|

* 2F-QMPSB
* 4-HTMPIPO
* 5F-PY-PICA
* 5F-PY-PINACA
* 5F-3-pyridinoylindole
* A-836,339
* A-955,840
* Abnormal cannabidiol
* AB-001
* BzODZ-EPyr
* AM-1248
* AM-1714
* AZ-11713908
* AZD-1940
* BAY 38-7271
* BAY 59-3074
* BIM-018
* CB-13
* CB-86
* CBS-0550
* CUMYL-4CN-B7AICA
* 5F-CUMYL-P7AICA
* CUMYL-PEGACLONE
* FUBIMINA
* GSK-554,418A
* GW-842,166X
* JTE 7-31
* LASSBio-881
* LBP-1
* Leelamine
* MDA-7
* MDA-19
* MEPIRAPIM
* NESS-040C5
* NMP-7
* O-889
* O-1269
* O-1270
* O-1399
* O-1602
* O-2220
* Olorinab
* PF-03550096
* PSB-SB-1202
* PTI-1
* PTI-2
* PTI-3
* QMPSB
* S-444,823
* SER-601
* Tedalinab
* URB-447
* VSN-16
* WIN 56,098

Allosteric CBR ligands|

* Org 27569
* Org 27759
* Org 29647
* RTI-371
* Pregnenolone

Endocannabinoid
enhancers
(inactivation inhibitors)|

* 4-Nonylphenylboronic acid
* AM-404
* Arachidonoyl serotonin
* Arvanil
* BIA 10-2474
* Biochanin A
* CAY-10401
* CAY-10429
* Genistein
* Guineesine
* IDFP
* JNJ 1661010
* JNJ-42165279
* JZL184
* JZL195
* Kaempferol
* LY-2183240
* MK-4409
* O-1624
* O-2093
* Oleoylethanolamide (OEA)
* Olvanil
* Palmitoylethanolamide (PEA)
* PF-04457845
* PF-622
* PF-750
* PF-3845
* PHOP
* URB-447
* URB-597
* URB-602
* URB-754
* VDM-11

Anticannabinoids
(antagonists/inverse
agonists/antibodies)|

* AM-251
* AM-281
* AM-630
* AM-1387
* AM-4113
* AM-6527
* AM-6545
* BML-190
* Brizantin (Бризантин)
* CAY-10508
* CB-25
* CB-52
* CB-86
* Dietressa (Диетресса)
* Drinabant (AVE1625)
* Hemopressin
* Ibipinabant (SLV319)
* JTE-907
* LH-21
* LY-320,135
* MDA-77
* MJ-15
* MK-9470
* NESS-0327
* NIDA-41020
* O-606
* O-1184
* O-1248
* O-1918
* O-2050
* O-2654
* Otenabant (CP-945,598)
* PF-514273
* PipISB
* PSB-SB-487
* Rimonabant (SR141716)
* Rosonabant (E-6776)
* SR-144,528
* Surinabant (SR147778)
* Taranabant (MK-0364)
* TM-38837
* VCHSR

* See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
* List of: AM cannabinoids
* JWH cannabinoids
* Designer drugs § Synthetic cannabimimetics

* v
* t
* e

Cannabinoid receptor modulators

Receptor
(ligands)</small>|

| CB1|

* Agonists (abridged; see here for more): 2-AG
* 2-AGE (noladin ether)
* 11-Hydroxy-THC
* α-Amyrin · β-Amyrin
* AB-CHMINACA
* AM-1172
* AM-1220
* AM-1221
* AM-1235
* AM-2201
* AM-2232
* Anandamide
* Arvanil
* 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

* Antagonists: AM-251
* AM-6545
* Cannabidiol
* Cannabigerol
* Drinabant
* Falcarinol (carotatoxin)
* Hemopressin
* Ibipinabant
* LY-320,135
* MK-9470
* NESS-0327
* O-2050
* Otenabant
* PF-514273
* PipISB
* Rimonabant
* Rosonabant
* Surinabant
* Taranabant
* THCV
* TM-38837
* VCHSR
* Virodhamine

* Antibodies: Brizantin (Бризантин)
* Dietressa (Диетресса)

* Unknown/unsorted: MAFP

|

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-1172
* 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-73
* JWH-133
* L-759,633
* L-759,656
* Lenabasum (anabasum)
* Magnolol
* MDA-19
* Nabitan
* NADA
* Olorinab (APD-371)
* PF-03550096
* S-444,823
* SER-601
* Serinolamide A
* UR-144
* Tedalinab
* THC (dronabinol)
* THCV
* Tetrahydromagnolol
* Virodhamine

* Antagonists: 4-O-Methylhonokiol
* AM-630
* BML-190
* Cannabidiol
* Honokiol
* JTE-907
* SR-144,528
* WIN 54,461
* WIN 56,098

NAGly
(GPR18)|

* Agonists: Abnormal cannabidiol
* ACPA
* AM251
* Anandamide
* Cannabidiol
* NADGly
* THC (dronabinol)
* O-1602

* Antagonists: CID-85469571
* O-1918

GPR55|

* Agonists: 2-AGE (noladin ether)
* 2-ALPI
* Abnormal cannabidiol
* AM-251
* CID1011163
* CID1252842
* CID1792579
* CP 55,940
* GSK-494581A
* Lysophosphatidylinositol
* ML-184
* ML-185
* ML-186
* O-1602
* Oleoylethanolamide
* Palmitoylethanolamide
* THC (dronabinol)

* Antagonists: Cannabidiol
* CID-16020046
* ML-191
* ML-192
* ML-193
* O-1918
* PSB-SB-487
* PSB-SB-1202
* PSB-SB-1203
* Tetrahydromagnolol

GPR119|

* Agonists: 2-Oleoylglycerol
* Anandamide
* APD668
* AR-231,453
* AS-1269574
* MBX-2982
* N-Oleoyldopamine
* Oleoylethanolamide
* Olvanil
* PSN-375,963
* PSN-632,408

Unsorted|

* Agonists: Revosimeline

Transporter
(modulators)|

| eCBTs|

* Inhibitors: 5'-DMH-CBD
* AM-404
* AM-1172
* Arachidonoyl serotonin
* Arvanil
* Cannabidiol
* Guineensine
* LY-2183240
* O-2093
* OMDM-2
* Paracetamol (acetaminophen)
* SB-FI-26
* UCM-707
* URB-597
* VDM-11
* WOBE490
* WOBE491
* WOBE492

|

Enzyme
(modulators)|

| FAAH|

* Inhibitors: 4-Nonylphenylboronic acid
* AACOCF3
* AM-404
* Arachidonoyl serotonin
* BIA 10-2474
* Biochanin A
* Genistein
* IDFP
* JNJ-1661010
* JNJ-42165279
* JZL-195
* Kaempferol
* LY-2183240
* MAFP
* Palmitoylisopropylamide
* Paracetamol (acetaminophen)
* PF-3845
* PF-04457845
* PF-750
* SA-47
* SA-57
* TAK 21d
* TC-F 2
* UCM710
* URB-597

* Activators: PDP-EA

|

MAGL|

* Inhibitors: ABX-1431
* IDFP
* JJKK 048
* JW 642
* JZL-184
* JZL-195
* JZP-361
* KML 29
* MAFP
* MJN110
* NAM
* Pristimerin
* URB-602

ABHD6|

* Inhibitors: JZP-169
* JZP-430
* KT182
* KT185
* KT195
* KT203
* LEI-106
* ML294
* ML295
* ML296
* UCM710
* WWL-70

ABHD12|

* Inhibitors: Betulinic acid
* Maslinic acid
* MAFP
* Oleanolic acid
* Orlistat (tetrahydrolipstatin)
* Ursolic acid

Others|

* Precursors: Phosphatidylethanolamine
* NAPE
* Diacylglycerol

* Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
* ARN-272 (FAAH-like anandamide transporter inhibitor)

See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)

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Original source: https://en.wikipedia.org/wiki/JWH-133. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:JWH-133&oldid=4176394"
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[CBR]: Cannabinoid receptor
*[CB1]: Cannabinoid receptor type 1
*[CB2]: Cannabinoid receptor type 2
*[NAGly]: N-Arachidonyl glycine receptor
*[GPR18]: G protein-coupled receptor 18
*[GPR55]: G protein-coupled receptor 55
*[GPR119]: G protein-coupled receptor 119
*[eCBTs]: Endocannabinoid transporter
*[FAAH]: Fatty acid amide hydrolase
*[ABHD6]: alpha/beta-Hydrolase domain containing 6
*[ABHD12]: alpha/beta-Hydrolase domain containing 12