11-Hydroxy-THC: Difference between revisions

Browse history interactively ← Previous edit Next edit →Content deleted Content addedVisual WikitextInline

Revision as of 15:17, 13 April 2024 editKimen8 (talk \| contribs)Extended confirmed users5,112 edits Undid revision 1218671114 by Mfernflower (talk) change makes it less accurateTags: Undo Reverted Mobile edit Mobile web edit Advanced mobile edit← Previous edit		Revision as of 03:37, 14 April 2024 edit undoKimen8 (talk \| contribs)Extended confirmed users5,112 edits Restored revision 1215192441 by Kimen8 (talk): Some changes are not accurate, needlessly dumbs down parts and removes internal linksTags: Twinkle Undo Next edit →
Line 42:		Line 42:
	}}		}}

	'''11-Hydroxy-Δ<sup>9</sup>-tetrahydrocannabinol''' ('''11-OH-Δ<sup>9</sup>-THC''', alternatively numbered as '''7-OH-Δ<sup>1</sup>-THC'''), usually referred to ~~in ]~~ as '''11-hydroxy-THC''' is the main active ] of ] (THC), which is formed in the body after Δ<sup>9</sup>-THC is consumed.<ref name=Kraemer2007>{{cite journal \| vauthors = Kraemer T, Paul LD \| title = Bioanalytical procedures for determination of drugs of abuse in blood \| journal = Analytical and Bioanalytical Chemistry \| volume = 388 \| issue = 7 \| pages = 1415–1435 \| date = August 2007 \| pmid = 17468860 \| doi = 10.1007/s00216-007-1271-6 \| s2cid = 32917584 }}</ref><ref name=Huestis2005>{{cite book \| vauthors = Huestis MA \| title = Cannabinoids \| chapter = Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol \| series = Handbook of Experimental Pharmacology \| volume = 168 \| pages = 657–690 \| date = 2005 \| issue = <!-- none --> \| pmid = 16596792 \| doi = 10.1007/3-540-26573-2_23 \| isbn = 3-540-22565-X }}</ref>		'''11-Hydroxy-Δ<sup>9</sup>-tetrahydrocannabinol''' ('''11-OH-Δ<sup>9</sup>-THC''', alternatively numbered as '''7-OH-Δ<sup>1</sup>-THC'''), usually referred to as '''11-hydroxy-THC''' is the main active ] of ] (THC), which is formed in the body after Δ<sup>9</sup>-THC is consumed.<ref name=Kraemer2007>{{cite journal \| vauthors = Kraemer T, Paul LD \| title = Bioanalytical procedures for determination of drugs of abuse in blood \| journal = Analytical and Bioanalytical Chemistry \| volume = 388 \| issue = 7 \| pages = 1415–1435 \| date = August 2007 \| pmid = 17468860 \| doi = 10.1007/s00216-007-1271-6 \| s2cid = 32917584 }}</ref><ref name=Huestis2005>{{cite book \| vauthors = Huestis MA \| title = Cannabinoids \| chapter = Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol \| series = Handbook of Experimental Pharmacology \| volume = 168 \| pages = 657–690 \| date = 2005 \| issue = <!-- none --> \| pmid = 16596792 \| doi = 10.1007/3-540-26573-2_23 \| isbn = 3-540-22565-X }}</ref>

	After ], THC is ] inside the body by ] enzymes such as ] and ] into 11-hydroxy-THC and then further metabolized by ~~cytochrome~~ ~~enzymes~~ to form ] which is inactive at the CB<sub>1</sub> receptors;<ref name=Huestis2005/> and further ] to form 11-nor-Δ<sup>9</sup>-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ<sup>9</sup>-THC-COOH-glu)<ref name="Stout_2014">{{cite journal \| vauthors = Stout SM, Cimino NM \| title = Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review \| journal = Drug Metabolism Reviews \| volume = 46 \| issue = 1 \| pages = 86–95 \| date = February 2014 \| pmid = 24160757 \| doi = 10.3109/03602532.2013.849268 \| s2cid = 29133059 \| url = https://zenodo.org/record/1093138 }}</ref> in the liver, from where it is subsequently excreted through feces and urine (via ] from the liver).<ref name="Grotenhermen_2003">{{cite journal \| vauthors = Grotenhermen F \| title = Pharmacokinetics and pharmacodynamics of cannabinoids \| journal = Clinical Pharmacokinetics \| volume = 42 \| issue = 4 \| pages = 327–360 \| date = 2003 \| pmid = 12648025 \| doi = 10.2165/00003088-200342040-00003 \| s2cid = 25623600 }}</ref> Both metabolites, along with THC, can be assayed in ~~blood~~ drug tests.<ref name=Kraemer2007/>		After ], THC is ] inside the body by ] enzymes such as ] and ] into 11-hydroxy-THC and then further metabolized by the ] and ] enzyme to form ] (THC-COOH) which is inactive at the CB<sub>1</sub> receptors;<ref name=Huestis2005/> and further ] to form 11-nor-Δ<sup>9</sup>-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ<sup>9</sup>-THC-COOH-glu)<ref name="Stout_2014">{{cite journal \| vauthors = Stout SM, Cimino NM \| title = Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review \| journal = Drug Metabolism Reviews \| volume = 46 \| issue = 1 \| pages = 86–95 \| date = February 2014 \| pmid = 24160757 \| doi = 10.3109/03602532.2013.849268 \| s2cid = 29133059 \| url = https://zenodo.org/record/1093138 }}</ref> in the liver, from where it is subsequently excreted through feces and urine (via ] from the liver).<ref name="Grotenhermen_2003">{{cite journal \| vauthors = Grotenhermen F \| title = Pharmacokinetics and pharmacodynamics of cannabinoids \| journal = Clinical Pharmacokinetics \| volume = 42 \| issue = 4 \| pages = 327–360 \| date = 2003 \| pmid = 12648025 \| doi = 10.2165/00003088-200342040-00003 \| s2cid = 25623600 }}</ref> Both metabolites, along with THC, can be assayed in drug tests.<ref name=Kraemer2007/>

	11-hydroxy-THC can be formed after consumption of ~~cannabis~~ from inhalation (vaping ~~and~~ smoking) and oral (~~swallowed~~ or sublingual) use, although levels of 11-hydroxy-THC are typically higher when ~~oral~~ ~~forms~~ of ~~the plant are used~~.<ref name="Huestis_1992">{{cite journal \| vauthors = Huestis MA, Henningfield JE, Cone EJ \| title = Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana \| journal = Journal of Analytical Toxicology \| volume = 16 \| issue = 5 \| pages = 276–282 \| date = 1992 \| pmid = 1338215 \| doi = 10.1093/jat/16.5.276 }}</ref><ref name="Karschner_2009">{{cite journal \| vauthors = Karschner EL, Schwilke EW, Lowe RH, Darwin WD, Herning RI, Cadet JL, Huestis MA \| title = Implications of plasma Delta9-tetrahydrocannabinol, 11-hydroxy-THC, and 11-nor-9-carboxy-THC concentrations in chronic cannabis smokers \| journal = Journal of Analytical Toxicology \| volume = 33 \| issue = 8 \| pages = 469–477 \| date = October 2009 \| pmid = 19874654 \| pmc = 3159863 \| doi = 10.1093/jat/33.8.469 }}</ref>		11-hydroxy-THC can be formed after consumption of THC from inhalation (vaping, smoking) and oral (by mouth, edible, sublingual) use, although levels of 11-hydroxy-THC are typically higher when eaten compared to inhalation.<ref name="Huestis_1992">{{cite journal \| vauthors = Huestis MA, Henningfield JE, Cone EJ \| title = Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana \| journal = Journal of Analytical Toxicology \| volume = 16 \| issue = 5 \| pages = 276–282 \| date = 1992 \| pmid = 1338215 \| doi = 10.1093/jat/16.5.276 }}</ref><ref name="Karschner_2009">{{cite journal \| vauthors = Karschner EL, Schwilke EW, Lowe RH, Darwin WD, Herning RI, Cadet JL, Huestis MA \| title = Implications of plasma Delta9-tetrahydrocannabinol, 11-hydroxy-THC, and 11-nor-9-carboxy-THC concentrations in chronic cannabis smokers \| journal = Journal of Analytical Toxicology \| volume = 33 \| issue = 8 \| pages = 469–477 \| date = October 2009 \| pmid = 19874654 \| pmc = 3159863 \| doi = 10.1093/jat/33.8.469 }}</ref>

	== Pharmacology ==		== Pharmacology ==
Line 52:		Line 52:

	== Research ==		== Research ==
	In an '']'' analysis by the ] on ] it was found that 11-OH-Δ<sup>9</sup>-THC had the 3rd highest ] inhibitor activity against ] out of all the cannabinoids tested within that study but not as high as the ~~known~~ ] ] (56% ~~for~~ 11-OH-Δ<sup>9</sup>-THC vs 100% ~~for~~ GC376).<ref>{{cite journal \| vauthors = Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H \| title = Identification of SARS-CoV-2 Main Protease Inhibitors from a Library of Minor Cannabinoids by Biochemical Inhibition Assay and Surface Plasmon Resonance Characterized Binding Affinity \| journal = Molecules \| volume = 27 \| issue = 18 \| page = 6127 \| date = September 2022 \| pmid = 36144858 \| pmc = 9502466 \| doi = 10.3390/molecules27186127 \| doi-access = free }}</ref>		In an '']'' analysis by the ] on ] it was found that 11-OH-Δ<sup>9</sup>-THC had the 3rd highest ] inhibitor activity against ] out of all the cannabinoids tested within that study but not as high as the ] ] (56% 11-OH-Δ<sup>9</sup>-THC vs 100% GC376).<ref>{{cite journal \| vauthors = Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H \| title = Identification of SARS-CoV-2 Main Protease Inhibitors from a Library of Minor Cannabinoids by Biochemical Inhibition Assay and Surface Plasmon Resonance Characterized Binding Affinity \| journal = Molecules \| volume = 27 \| issue = 18 \| page = 6127 \| date = September 2022 \| pmid = 36144858 \| pmc = 9502466 \| doi = 10.3390/molecules27186127 \| doi-access = free }}</ref>

	== See also ==		== See also ==

Revision as of 03:37, 14 April 2024

Active metabolite of Δ9-THC For the isomer of this chemical inherited from Δ-tetrahydrocannabinol, see 11-Hydroxy-Delta-8-THC. Pharmaceutical compound

11-Hydroxy-THC
Clinical data


Drug class	Cannabinoid
Legal status
Legal status	UK: Class B
Identifiers
IUPAC name (6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzochromen-1-ol
CAS Number	36557-05-8
PubChem CID	37482
ChemSpider	34385
UNII	9VY04N5SLB
KEGG	C22778
CompTox Dashboard (EPA)	DTXSID50190061
ECHA InfoCard	100.164.583
Chemical and physical data
Formula	C₂₁H₃₀O₃
Molar mass	330.468 g·mol
3D model (JSmol)	Interactive image
SMILES Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC
InChI InChI=1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3 Key:YCBKSSAWEUDACY-UHFFFAOYSA-N
(what is this?) (verify)

11-Hydroxy-Δ-tetrahydrocannabinol (11-OH-Δ-THC, alternatively numbered as 7-OH-Δ-THC), usually referred to as 11-hydroxy-THC is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after Δ-THC is consumed.

After cannabis consumption, THC is metabolized inside the body by cytochrome P450 enzymes such as CYP2C9 and CYP3A4 into 11-hydroxy-THC and then further metabolized by the dehydrogenase and CYP2C9 enzyme to form 11-nor-9-carboxy-THC (THC-COOH) which is inactive at the CB₁ receptors; and further glucuronidated to form 11-nor-Δ-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ-THC-COOH-glu) in the liver, from where it is subsequently excreted through feces and urine (via bile from the liver). Both metabolites, along with THC, can be assayed in drug tests.

11-hydroxy-THC can be formed after consumption of THC from inhalation (vaping, smoking) and oral (by mouth, edible, sublingual) use, although levels of 11-hydroxy-THC are typically higher when eaten compared to inhalation.

Pharmacology

Like Δ-THC, 11-hydroxy-THC is a partial agonist at the cannabinoid receptor CB₁, but with significantly higher binding affinity (K_i = 0.37 nM compared to Δ-THC K_i = 35 nM). With respect to cAMP inhibition at CB₁ it displays a similar efficacy to that of Δ-THC (EC₅₀ = 11 nM vs. EC₅₀ = 5.2 nM, respectively), but a lower maximum response (E_max = 28% vs. E_max = 70%).

Research

In an in vitro analysis by the University of Rhode Island on cannabinoids it was found that 11-OH-Δ-THC had the 3rd highest 3C-like protease inhibitor activity against COVID-19 out of all the cannabinoids tested within that study but not as high as the antiviral drug GC376 (56% 11-OH-Δ-THC vs 100% GC376).

References

^ Kraemer T, Paul LD (August 2007). "Bioanalytical procedures for determination of drugs of abuse in blood". Analytical and Bioanalytical Chemistry. 388 (7): 1415–1435. doi:10.1007/s00216-007-1271-6. PMID 17468860. S2CID 32917584.
^ Huestis MA (2005). "Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol". Cannabinoids. Handbook of Experimental Pharmacology. Vol. 168. pp. 657–690. doi:10.1007/3-540-26573-2_23. ISBN 3-540-22565-X. PMID 16596792.
Stout SM, Cimino NM (February 2014). "Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review". Drug Metabolism Reviews. 46 (1): 86–95. doi:10.3109/03602532.2013.849268. PMID 24160757. S2CID 29133059.
Grotenhermen F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clinical Pharmacokinetics. 42 (4): 327–360. doi:10.2165/00003088-200342040-00003. PMID 12648025. S2CID 25623600.
Huestis MA, Henningfield JE, Cone EJ (1992). "Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana". Journal of Analytical Toxicology. 16 (5): 276–282. doi:10.1093/jat/16.5.276. PMID 1338215.
Karschner EL, Schwilke EW, Lowe RH, Darwin WD, Herning RI, Cadet JL, Huestis MA (October 2009). "Implications of plasma Delta9-tetrahydrocannabinol, 11-hydroxy-THC, and 11-nor-9-carboxy-THC concentrations in chronic cannabis smokers". Journal of Analytical Toxicology. 33 (8): 469–477. doi:10.1093/jat/33.8.469. PMC 3159863. PMID 19874654.
^ Zagzoog A, Cabecinha A, Abramovici H, Laprairie RB (26 August 2022). "Modulation of type 1 cannabinoid receptor activity by cannabinoid by-products from Cannabis sativa and non-cannabis phytomolecules". Frontiers in Pharmacology. 13: 956030. doi:10.3389/fphar.2022.956030. PMC 9458935. PMID 36091813.
Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H (September 2022). "Identification of SARS-CoV-2 Main Protease Inhibitors from a Library of Minor Cannabinoids by Biochemical Inhibition Assay and Surface Plasmon Resonance Characterized Binding Affinity". Molecules. 27 (18): 6127. doi:10.3390/molecules27186127. PMC 9502466. PMID 36144858.

Cannabinoids

Phytocannabinoids
(comparison)

Cannabibutols	CBB
Cannabichromenes	CBC CBCA CBCA-A CBCB CBCBA CBCP CBCPA CBCV CBCVA CBCQ
Cannabicyclols	CBL CBLA CBLB CBLP CBLPA CBLV CBLVA
Cannabidiols	CBD CBDA CBD-C1 CBD-C5 CBDB CBDBA CBDD CBDH CBDP CBDPA CBDM CBDMA CBDV CBDVA CBDQ
Cannabielsoins	CBE CBEA CBEA-A CBEA-B CBEB CBEP CBEPA CBEV
Cannabigerols	CBG CBGA CBGB CBGBA CBGM CBGAM CBGP CBGPA CBNR CBNRA CBNRA-A CBGV CBGVA CBGVA-A CBGQ
Cannabiphorols	CBP
Cannabinols	CBN CBNA CBN-C1 CBN-C2 CBN-C4 CBNM CBND CBNDA CBNP CBNPA CBVD CBVDA
Cannabitriols	CBT CBTA CBTB CBTV CBTVA CBTP CBTPA
Cannabivarins	CBV CBVA
Delta-8-tetrahydrocannabinols	Delta-8-THC Delta-8-THCA Delta-8-THCA-A Delta-8-THCB Delta-8-THCP Delta-8-THCV
Delta-9-tetrahydrocannabinols	Delta-9-THC (THC) THCA THCMA THCA-A THCA-B THCBA THCA-C4 THCC THCA-C1 THCA-A-C1 THCA-B-C1 THCB THCH THCP THCPA THCV THCVA THCQ
Delta-10-Tetrahydrocannabinols	Delta-10-THC
Miscellaneous cannabinoids	Δ8-iso-THC Δ4(8)-iso-THC 7,8-Dihydrocannabinol 8,9-Dihydrocannabidiol CBCF Cannabicitran CBF Cannabiglendol CBM CBR CBRPA Caryophyllene DCBF Alkylamides Epigallocatechin gallate Gallocatechol Hexahydrocannabinol (HHC) Perrottetinene Serinolamide A Yangonin
Active metabolites	3'-OH-THC 7-OH-CBD 8,11-DiOH-THC 11-COOH-THC 11-OH-CBN 11-OH-HHC 11-OH-Δ8-THC 11-OH-Δ9-THC

Endocannabinoids

Synthetic
cannabinoid
receptor
agonists /
neocannabinoids

Classical cannabinoids (dibenzopyrans)	1,2-Didehydro-3-oxo-THCO 9-OH-HHC 9-Nor-9β-HHC 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 AM-7438 AM-11245 AMG-1 AMG-3 AMG-36 AMG-41 CP 42,096 Delta-3-THC Delta-4-THC Delta-7-THC Delta-10-THC Dexanabinol (HU-211) DMHP Dronabinol HU-210 HU-243 JWH-051 JWH-056 JWH-057 JWH-065 JWH-091 JWH-102 JWH-103 JWH-124 JWH-130 JWH-133 JWH-138 JWH-139 JWH-142 JWH-143 JWH-161 JWH-186 JWH-187 JWH-188 JWH-189 JWH-190 JWH-191 JWH-215 JWH-216 JWH-217 JWH-224 JWH-225 JWH-226 JWH-227 JWH-229 JWH-230 JWH-233 JWH-247 JWH-254 JWH-256 JWH-277 JWH-278 JWH-298 JWH-299 JWH-300 JWH-301 JWH-310 JWH-336 JWH-338 JWH-339 JWH-340 JWH-341 JWH-349 JWH-350 JWH-352 JWH-353 JWH-354 JWH-355 JWH-356 JWH-357 JWH-358 JWH-359 JWH-360 JWH-361 JWH-362 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 SP-111 THC hemisuccinate THC-O-acetate THC-O-phosphate
Non-classical cannabinoids	Cannabicyclohexanol Cannabinor CBD-DMH CP 47,497 (C6)-CP 47,497 (C9)-CP 47,497 CP 55,244 CP 55,940 Delta-6-Cannabidiol Etrinabdione 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 Onternabez (HU-308) SPA-229 Tinabinol
Adamantoylindoles	5F-AKB-48 APICA STS-135
Benzimidazoles	AZ-11713908 AZD-1940 BIM-018 FUBIMINA MCHB-1 PF-03550096 RQ-00202730
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
Cyclohexylphenols	CP-47,947 CP-55,940
Eicosanoids	AM-883 AM-1346 ACEA ACPA Methanandamide (AM-356) O-585 O-689 O-1812 O-1860 O-1861
Indazole-3- carboxamides	4F-MDMB-BINACA 4'Cl-CUMYL-PINACA 4'F-CUMYL-5F-PINACA 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-BINACA ADB-BUTINACA ADB-CHMINACA ADB-HEXINACA ADB-FUBINACA ADB-PINACA ADB-4en-PINACA ADB-5'Br-PINACA ADMB-3TMS-PRINACA Adamantyl-THPINACA ADSB-FUB-187 AMB-CHMINACA AMB-FUBINACA APINACA (AKB48) APP-FUBINACA CUMYL-3TMS-PRINACA CUMYL-4CN-BINACA CUMYL-CBMINACA CUMYL-CHSINACA CUMYL-FUBINACA CUMYL-NBMINACA CUMYL-PINACA CUMYL-THPINACA CUMYL-TSINACA EMB-FUBINACA FUB-APINACA MDMB-4en-PINACA MDMB-5Br-INACA MDMB-BINACA MDMB-CHMINACA MDMB-FUBINACA MN-18 PX-2 PX-3 THQ-PINACA
Indole-3-carboxamides	4'F-CUMYL-5F-PICA 5F-ADBICA 5F-EDMB-PICA 5F-MDMB-PICA 5F-NNE1 5F-PCN 5F-SDB-006 AB-FUBICA AB-PICA ADBICA ADB-FUBICA APICA BMS-F CUMYL-BICA CUMYL-CBMICA CUMYL-CHMICA CUMYL-NBMICA 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
Naphthoylindazoles	THJ-018 THJ-2201
Naphthoylindoles	5F-JWH-398 AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 CHM-081 EAM-2201 FUB-JWH-018 JWH-004 JWH-007 JWH-009 JWH-011 JWH-015 JWH-016 JWH-018 JWH-019 JWH-020 JWH-042 JWH-043 JWH-046 JWH-047 JWH-048 JWH-049 JWH-050 JWH-070 JWH-072 JWH-073 JWH-076 JWH-077 JWH-079 JWH-080 JWH-081 JWH-082 JWH-083 JWH-093 JWH-094 JWH-095 JWH-096 JWH-097 JWH-098 JWH-099 JWH-100 JWH-116 JWH-120 JWH-122 JWH-148 JWH-149 JWH-151 JWH-153 JWH-159 JWH-160 JWH-163 JWH-164 JWH-165 JWH-166 JWH-180 JWH-181 JWH-182 JWH-189 JWH-193 JWH-198 JWH-200 JWH-210 JWH-211 JWH-212 JWH-213 JWH-234 JWH-235 JWH-236 JWH-239 JWH-240 JWH-241 JWH-242 JWH-258 JWH-259 JWH-260 JWH-261 JWH-262 JWH-265 JWH-266 JWH-267 JWH-268 JWH-387 JWH-398 JWH-416 JWH-417 JWH-422 JWH-423 JWH-424 JWH-425 MAM-1220 MAM-2201 NE-CHMIMO
Naphthoylpyrroles	JWH-030 JWH-031 JWH-032 JWH-033 JWH-036 JWH-044 JWH-045 JWH-145 JWH-146 JWH-147 JWH-150 JWH-156 JWH-243 JWH-244 JWH-245 JWH-246 JWH-292 JWH-293 JWH-307 JWH-308 JWH-309 JWH-346 JWH-347 JWH-348 JWH-363 JWH-364 JWH-365 JWH-366 JWH-367 JWH-368 JWH-369 JWH-370 JWH-371 JWH-372 JWH-373
Naphthylmethylindenes	JWH-171 JWH-176 JWH-220
Naphthylmethylindoles	JWH-175 JWH-184 JWH-185 JWH-192 JWH-194 JWH-195 JWH-196 JWH-197 JWH-199
Phenylacetylindoles	Cannabipiperidiethanone JWH-167 JWH-201 JWH-202 JWH-203 JWH-204 JWH-205 JWH-206 JWH-207 JWH-208 JWH-209 JWH-237 JWH-248 JWH-249 JWH-250 JWH-251 JWH-252 JWH-253 JWH-302 JWH-303 JWH-304 JWH-305 JWH-306 JWH-311 JWH-312 JWH-313 JWH-314 JWH-315 JWH-316 RCS-8
Pyrazolecarboxamides	5F-AB-FUPPYCA 5F-AMPPPCA AB-CHFUPYCA
Tetramethylcyclo- propanoylindazoles	FAB-144
Tetramethylcyclo- propanoylindoles	5Br-UR-144 5Cl-UR-144 A-796,260 A-834,735 FUB-144 UR-144 XLR-11 XLR-12
Others	2F-QMPSB 4-HTMPIPO 4CN-CUMYL-BUT7AICA 5F-PY-PICA 5F-PY-PINACA 5F-3-pyridinoylindole 5F-ADB-P7AICA 5F-CUMYL-P7AICA 5F-CUMYL-PEGACLONE A-836,339 A-955,840 A-PBITMO A-PONASA Abnormal cannabidiol AB-001 ADB-FUBHQUCA ADB-FUBIATA ADB-P7AICA AM-1248 AM-1714 BAY 38-7271 BAY 59-3074 BzODZ-EPyr CB-13 CB-86 CBS-0550 CUMYL-4CN-B7AICA CUMYL-CB-MEGACLONE CUMYL-CH-MEGACLONE CUMYL-PEGACLONE EG-018 GSK-554,418A GW-842,166X JTE 7-31 LASSBio-881 LBP-1 Leelamine MDA-7 MDA-19 MEPIRAPIM NESS-040C5 NMDMSB 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 S-777,469 SER-601 Tedalinab URB-447 VSN-16 WIN 55,212-2 WIN 56,098

Allosteric CBRTooltip Cannabinoid receptor ligands

Endocannabinoid
enhancers
(inactivation inhibitors)

Anticannabinoids
(antagonists/inverse
agonists/antibodies)

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

Cannabinoid receptor modulators

Receptor
(ligands)

CB₁Tooltip Cannabinoid receptor type 1

Agonists (abridged, full list)	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
Inverse agonists	AM-251 INV-202 Monlunabant Rimonabant Surinabant Taranabant TM-38837 Zevaquenabant
Antagonists	AM-6545 Cannabidiol Cannabigerol Drinabant Falcarinol (carotatoxin) Hemopressin Ibipinabant LY-320,135 MK-9470 NESS-0327 O-2050 Otenabant PF-514273 PipISB Rosonabant Selonabant THCV VCHSR Virodhamine

CB₂Tooltip Cannabinoid receptor type 2

Agonists

Antagonists

NAGly
(GPR18)

Agonists	Abnormal cannabidiol ACPA AM251 Anandamide Cannabidiol NADGly THC (dronabinol) O-1602
Antagonists	PSB-CB5 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

Transporter
(modulators)

eCBTsTooltip Endocannabinoid transporter	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)

FAAHTooltip Fatty acid amide hydrolase	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-750 Redafamdastat (JZP-150, PF-04457845) 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)

Categories:

Revision as of 03:37, 14 April 2024

Pharmacology

Research

See also

References