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Tetrahydrocannabiorcol Identifiers IUPAC name (6aR,10aR)-3,6,6,9-tetramethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA) DTXSID901336645 Chemical and physical data Formula C 17H 22O 2Molar mass 258.361 g·mol−13D model (JSmol) SMILES CC1=C[C@@H]2[C@@H](CC1)C(OC3=CC(=CC(=C23)O)C)(C)C InChI InChI=1S/C17H22O2/c1-10-5-6-13-12(7-10)16-14(18)8-11(2)9-15(16)19-17(13,3)4/h7-9,12-13,18H,5-6H2,1-4H3/t12-,13-/m1/s1 Key:WIDIPARNVYRVNW-CHWSQXEVSA-N
Δ9-Tetrahydrocannabiorcol (Δ9-THCC, (C1)-Δ9-THC) is a phytocannabinoid found in Cannabis pollen.[ 1] It is a homologue of THC and THCV with the alkyl side chain replaced by a smaller methyl group. Unlike THC and THCV, THCC has negligible affinity for the CB1 and CB2 cannabinoid receptors because of the smaller methyl group and does not have psychoactive effects as a result, but conversely it is significantly more potent than THC or THCV as an activator of the TRPA1 calcium channel which plays an important role in pain perception,[ 2] and it has been shown to produce analgesic effects via activation of spinal TRPA1 channels.[ 3] [ 4] THCC was studied by Roger Adams as early as 1942.[ 5]
See also [ edit ] Abnormal cannabidiol Cannabidiorcol O-1602 O-1918 Tetrahydrocannabiphorol Tetrahydrocannabutol References [ edit ] ^ Ross SA, ElSohly MA, Sultana GN, Mehmedic Z, Hossain CF, Chandra S (2005). "Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L". Phytochemical Analysis . 16 (1): 45– 8. Bibcode:2005PChAn..16...45R. doi:10.1002/pca.809 . PMID 15688956. ^ Bow EW, Rimoldi JM (2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry . 8: 17– 39. doi:10.4137/PMC.S32171. PMC 4927043 . PMID 27398024. ^ Andersson DA, Gentry C, Alenmyr L, Killander D, Lewis SE, Andersson A, et al. (November 2011). "TRPA1 mediates spinal antinociception induced by acetaminophen and the cannabinoid Δ(9)-tetrahydrocannabiorcol". Nature Communications . 2: 551. Bibcode:2011NatCo...2..551A. doi:10.1038/ncomms1559 . PMID 22109525. ^ Moparthi L, Survery S, Kreir M, Simonsen C, Kjellbom P, Högestätt ED, et al. (November 2014). "Human TRPA1 is intrinsically cold- and chemosensitive with and without its N-terminal ankyrin repeat domain". Proceedings of the National Academy of Sciences of the United States of America . 111 (47): 16901– 6. Bibcode:2014PNAS..11116901M. doi:10.1073/pnas.1412689111 . PMC 4250169 . PMID 25389312. ^ Adams R, Loewe S, Smith CM, McPhee WD (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII1" . Journal of the American Chemical Society . 64 (3): 694– 697. doi:10.1021/ja01255a061. TRP channel modulators TRPA Activators 4-Hydroxynonenal 4-Oxo-2-nonenal 5,6-EET 12S-HpETE 15-Deoxy-Δ12,14-prostaglandin J2 α-Sanshool (ginger, Sichuan and melegueta peppers) Acrolein Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi) AM404 ASP-7663 Bradykinin Cannabichromene (cannabis) Cannabidiol (cannabis) Cannabigerol (cannabis) Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery) Diallyl disulfide Dicentrine (Lindera spp.) Farnesyl thiosalicylic acid Formalin Gingerols (ginger) Hepoxilin A3 Hepoxilin B3 Hydrogen peroxide Icilin Isothiocyanate JT-010 Ligustilide (celery, Angelica acutiloba ) Linalool (Sichuan pepper, thyme) Methylglyoxal Methyl salicylate (wintergreen) N-Methylmaleimide Nicotine (tobacco) Oleocanthal (olive oil) Paclitaxel (Pacific yew) PF-4840154 Phenacyl chloride Polygodial (Dorrigo pepper) Shogaols (ginger, Sichuan and melegueta peppers) Tear gases Tetrahydrocannabinol (cannabis) Tetrahydrocannabiorcol Thiopropanal S-oxide (onion) Umbellulone (Umbellularia californica ) WIN 55,212-2 Blockers A-967079 AM-0902 Dehydroligustilide (celery) HC-030031 Nicotine (tobacco) PF-04745637 Ruthenium red
TRPC Activators Adhyperforin (St John's wort) Diacyl glycerol GSK1702934A Hyperforin (St John's wort) Substance P Blockers DCDPC DHEA-S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N-(p-Amylcinnamoyl)anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid
TRPM Activators ADP-ribose BCTC Calcium (intracellular) CIM-0216 Cold Coolact P Cooling Agent 10 Eucalyptol (eucalyptus) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol (mint) PMD 38 Pregnenolone sulfate Rutamarin (Ruta graveolens ) Steviol glycosides (e.g., stevioside) (Stevia rebaudiana ) Sweet tastants (e.g., glucose, fructose, sucrose; indirectly) Thio-BCTC WS-12 Blockers AMG-333 Capsazepine Clotrimazole DCDPC Elismetrep Flufenamic acid Meclofenamic acid Mefenamic acid N-(p-Amylcinnamoyl)anthranilic acid Nicotine (tobacco) Niflumic acid Ononetin PF-05105679 RQ-00203078 Ruthenium red Rutamarin (Ruta graveolens ) Tolfenamic acid TPPO TRPM4-IN-5
TRPML Activators EVP21 MK6-83 ML-SA1 ML2-SA1 PI(3,5)P2 SF-22 SN-2 Blockers
TRPP Activators Triptolide (Tripterygium wilfordii ) Blockers
TRPV Activators 2-APB 5,6-EET 9-HODE 9-oxoODE 12S-HETE 12S-HpETE 13-HODE 13-oxoODE 20-HETE α-Sanshool (ginger, Sichuan and melegueta peppers) Allicin (garlic) AM404 Anandamide Bisandrographolide (Andrographis paniculata ) Camphor (camphor laurel, rosemary, camphorweed, African blue basil, camphor basil) Cannabidiol (cannabis) Cannabidivarin (cannabis) Capsaicin (chili pepper) Carvacrol (oregano, thyme, pepperwort, wild bergamot, others) DHEA Diacyl glycerol Dihydrocapsaicin (chili pepper) Estradiol Eugenol (basil, clove) Evodiamine (Euodia ruticarpa ) Gingerols (ginger) GSK1016790A Heat Hepoxilin A3 Hepoxilin B3 Homocapsaicin (chili pepper) Homodihydrocapsaicin (chili pepper) Incensole (incense) Lysophosphatidic acid Low pH (acidic conditions) Menthol (mint) N-Arachidonoyl dopamine N-Oleoyldopamine N-Oleoylethanolamide Nonivamide (PAVA) (PAVA spray) Nordihydrocapsaicin (chili pepper) Paclitaxel (Pacific yew) Paracetamol (acetaminophen) Phenylacetylrinvanil Phorbol esters (e.g., 4α-PDD) Piperine (black pepper, long pepper) Polygodial (Dorrigo pepper) Probenecid Protons RhTx Rutamarin (Ruta graveolens ) Resiniferatoxin (RTX) (Euphorbia resinifera/pooissonii ) Shogaols (ginger, Sichuan and melegueta peppers) Tetrahydrocannabivarin (cannabis) Thymol (thyme, oregano) Tinyatoxin (Euphorbia resinifera/pooissonii ) Tramadol Vanillin (vanilla) Zucapsaicin Blockers α-Spinasterol (Vernonia tweediana ) AMG-517 AMG-9810 Asivatrep BCTC Cannabigerol (cannabis) Cannabigerolic acid (cannabis) Cannabigerovarin (cannabis) Cannabinol (cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamic acid GRC-6211 HC-067047 Lanthanum Mavatrep Meclofenamic acid N-(p-Amylcinnamoyl)anthranilic acid NGD-8243 Niflumic acid Pregnenolone sulfate RN-1734 RN-9893 Ruthenium red SB-366791 SB-705498 Tivanisiran Tolfenamic acid TRPV3-74a
See also: Receptor/signaling modulators • Ion channel modulators
Cannabinoids Phytocannabinoids(comparison) Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols CBD CBD-C1 CBD-C5 CBDB CBDD CBDH CBDP CBDM CBDV CBDQ Cannabielsoins Cannabigerols Cannabiphorols Cannabinols CBN CBNA CBN-C1 CBN-C2 CBN-C4 CBNM CBND CBNP CBVD Cannabitriols Cannabivarins Delta-3-tetrahydrocannabinols Delta-4-tetrahydrocannabinols Delta-7-tetrahydrocannabinols Delta-8-tetrahydrocannabinols Delta-8-THC Delta-8-THCB Delta-8-THCP Delta-8-THCV Delta-9-tetrahydrocannabinols Delta-9-THC (THC) THCH THCP THCV THCQ Delta-10-Tetrahydrocannabinols Delta-11-Tetrahydrocannabinols 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 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) Syntheticcannabinoidreceptoragonists /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 Cis-THC CP 42,096 Dexanabinol (HU-211) DMHP Dronabinol HHCP-O-acetate HHCH HU-210 HU-243 Iso-THC 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 THCP-O-acetate Non-classicalcannabinoids 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 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 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 A-CHMINACA 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-EINACA 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 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 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 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-3-pyridinoylindole 5F-ADB-P7AICA 5F-CUMYL-P7AICA 5F-CUMYL-PEGACLONE 5F-PY-PICA 5F-PY-PINACA A-836,339 A-955,840 A-PBITMO A-PONASA AB-001 ADB-FUBHQUCA ADB-FUBIATA ADB-P7AICA AM-1248 AM-1714 Abnormal cannabidiol 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-19 MDA-7 MEPIRAPIM NESS-040C5 NMDMSB NMP-7 O-1269 O-1270 O-1399 O-1602 O-2220 O-889 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 Vicasinabin WIN 55,212-2 WIN 56,098
Allosteric CBRTooltip Cannabinoid receptor ligands AEF0117 GAT100 Org 27569 Org 27759 Org 29647 PSNCBAM-1 Pregnenolone RTI-371 ZCZ-011 Endocannabinoidenhancers(inactivation inhibitors) 4-Nonylphenylboronic acid AM-404 Arachidonoyl serotonin ART26.12 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 O-7460 Oleoylethanolamide (OEA) Olvanil Palmitoylethanolamide (PEA) PF-04457845 PF-622 PF-750 PF-3845 PHOP UCM707 URB-447 URB-597 URB-602 URB-754 VDM-11 Anticannabinoids(antagonists/inverseagonists/antibodies) ABD459 AM-251 AM-281 AM-630 AM-1387 AM-4113 AM-6527 AM-6545 Amauromine ANEB-001 AZD-2207 BML-190 CAY-10508 CB-25 CB-52 CB-86 CE-178253 COR170 Drinabant (AVE1625) Hemopressin Ibipinabant (SLV319) JD-5037 JTE-907 LH-21 LY-320,135 MDA-77 MJ-15 MK-9470 Monlunabant MRL-650 NESS-0327 NIDA-41020 O-606 O-1184 O-1248 O-1918 O-2050 O-2654 Otenabant (CP-945,598) PF-514273 PGN36 PipISB PSB-SB-487 Rezosicone Rimonabant (SR141716) Rosonabant (E-6776) SLV 319 SR-144,528 Surinabant (SR147778) Taranabant (MK-0364) TC-C 14G TM-38837 VCHSR Voacamine Zevaquenabant See also: Cannabinoid receptor modulators (cannabinoids by pharmacology) List of: AM cannabinoids JWH cannabinoids Designer drugs § Synthetic cannabimimetics
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