11-Hydroxy-THC: Difference between revisions

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	'''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).<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 journal \| vauthors = Huestis MA \| title = Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol \| journal = Handbook of Experimental Pharmacology \| volume = 168 \| issue = 168 \| pages = 657–690 \| date = 2005 \| 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 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 journal \| vauthors = Huestis MA \| title = Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol \| journal = Handbook of Experimental Pharmacology \| volume = 168 \| issue = 168 \| pages = 657–690 \| date = 2005 \| 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 the ] and ] enzyme to form ] (THC-COOH) which is inactive at the CB1 receptors;<ref name=Huestis2005/> and further ] to form 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid glucuronide (delta-9-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> where it is excreted in both feces and urine.<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 compounds, along with THC, can be assayed in 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 CB1 receptors;<ref name=Huestis2005/> and further ] to form 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid glucuronide (delta-9-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> where it is excreted in both feces and urine.<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 compounds, along with THC, can be assayed in drug tests.<ref name=Kraemer2007/>

			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>
	THC administered orally results in higher 11-OH-THC plasma concentration compared to smoking. <ref name="pertwee">{{cite book \|last=Pertwee \|first=Robert\|date=2005 \|title=Cannabinoids Handbook of Experimental Pharmacology volume 168\|url= \|location=Germany \|publisher=Springer \|page=667 \|isbn=3-540-22565-X}}</ref>

			== Pharmacology ==
			In an analysis by the ] on ] it was found that 11-OH-D9-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-D9-THC) vs 100% GC376). <ref>https://www.mdpi.com/1420-3049/27/18/6127</ref>

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

Revision as of 18:44, 24 January 2023

Chemical compound 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
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 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-delta-9-tetrahydrocannabinol-9-carboxylic acid glucuronide (delta-9-THC-COOH-glu) where it is excreted in both feces and urine. Both compounds, 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

In an analysis by the University of Rhode Island on cannabinoids it was found that 11-OH-D9-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-D9-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". Handbook of Experimental Pharmacology. 168 (168): 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.
https://www.mdpi.com/1420-3049/27/18/6127

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 18:44, 24 January 2023

Pharmacology

See also

References