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Chemical compound
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 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
References
^ 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 .
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 )
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 )
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
TRPM
TRPML
TRPP
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
Phytocannabinoids (
comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols
Eicosanoids
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 Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
Endocannabinoid enhancers (inactivation inhibitors)
Anticannabinoids (antagonists/inverse agonists/antibodies)