Tetrahydrocannabiorcol
(6aR,10aR)-3,6,6,9-tetramethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number PubChem CID ChemSpider UNII Formula C 17 H 22 O 2 Molar mass 258.361 g·mol−1 3D model (JSmol )
CC1=C[C@@H]2[C@@H](CC1)C(OC3=CC(=CC(=C23)O)C)(C)C
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 , 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]
See also [ ]
References [ ]
^ Ross SA, ElSohly MA, Sultana GN, Mehmedic Z, Hossain CF, Chandra S. "Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L". Phytochemical Analysis . 16 (1): 45–8. 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. 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. doi :10.1073/pnas.1412689111 . PMC 4250169 . PMID 25389312 .
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-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 )
(celery )
Diallyl disulfide
Dicentrine (Lindera spp.)
Formalin
Gingerols (ginger )
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
(celery , Angelica acutiloba )
Linalool (Sichuan pepper , thyme )
Methylglyoxal
Methyl salicylate (wintergreen )
N-Methylmaleimide
Nicotine (tobacco )
Oleocanthal (olive oil )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
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
TRPC
Activators
Adhyperforin (St John's wort )
Diacyl glycerol
GSK1702934A
Hyperforin (St John's wort )
Substance P
Blockers
DHEA-S
Flufenamic acid
GSK417651A
Meclofenamic acid
N-(p-Amylcinnamoyl)anthranilic acid
Niflumic acid
Pregnenolone sulfate
Progesterone
Tolfenamic acid
TRPM
Activators
ADP-ribose
Calcium (intracellular)
CIM-0216
Cold
Cooling Agent 10
Eucalyptol (eucalyptus )
Geraniol
Hydroxycitronellal
Icilin
Linalool
Menthol (mint )
Pregnenolone sulfate
(Ruta graveolens )
Steviol glycosides (e.g., stevioside ) (Stevia rebaudiana )
Sweet tastants (e.g., glucose , fructose , sucrose ; indirectly)
WS-12
Blockers
AMG-333
Capsazepine
Clotrimazole
Flufenamic acid
Meclofenamic acid
Mefenamic acid
N-(p-Amylcinnamoyl)anthranilic acid
Nicotine (tobacco )
Niflumic acid
Ononetin
PF-05105679
RQ-00203078
Ruthenium red
(Ruta graveolens )
Tolfenamic acid
TPPO
TRPM4-IN-5
TRPML
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
(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-Oleoylethanolamide
Nonivamide (PAVA) (PAVA spray )
Nordihydrocapsaicin (chili pepper )
Paclitaxel (Pacific yew )
Paracetamol (acetaminophen)
Phenylacetylrinvanil
Phorbol esters (e.g., )
Piperine (black pepper , long pepper )
Polygodial (Dorrigo pepper )
Probenecid
Protons
RhTx
(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
Cannabigerol (cannabis )
Cannabigerolic acid (cannabis )
Cannabigerovarin (cannabis )
Cannabinol (cannabis )
Capsazepine
DHEA
DHEA-S
Flufenamic acid
GRC-6211
HC-067047
Lanthanum
Mavatrep
Meclofenamic acid
N-(p-Amylcinnamoyl)anthranilic acid
Niflumic acid
Pregnenolone sulfate
RN-9893
Ruthenium red
SB-366791
SB-705498
Tolfenamic acid
TRPV3-74a
See also: Receptor/signaling modulators • Ion channel modulators
Cannabinoids
Phytocannabinoids
Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabinols and cannabinodiols Cannabitriols Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols
Delta-9-THC (THC)
THCH
THCP
THCV
Miscellaneous cannabinoids 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 cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles
AM-630
AM-679
AM-694
AM-1241
AM-2233
GW-405,833 (L-768,242)
Pravadoline
RCS-4
WIN 54,461
Cyclohexylphenols Eicosanoids
ACEA
ACPA
Methanandamide (AM-356)
O-1812
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles
A-796,260
A-834,735
FUB-144
UR-144
XLR-11
XLR-12
Tetramethylcyclo- propylindoles Others
Allosteric CBR ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)
AM-251
AM-630
AM-6545
BML-190
Drinabant (AVE1625)
Hemopressin
Ibipinabant (SLV319)
JTE-907
LY-320,135
MK-9470
NESS-0327
O-1918
O-2050
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