Tetrahydrocannabiorcol

Tetrahydrocannabiorcol
Identifiers
	IUPAC name (6aR,10aR)-3,6,6,9-tetramethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol;
CAS Number	22972-65-2;
PubChem CID	22805649;
ChemSpider	18522304;
UNII	5D633LAJ19;
CompTox Dashboard (EPA)	DTXSID901336645 ;
Chemical and physical data
Formula	C17H22O2
Molar mass	258.361 g·mol−1
3D model (JSmol)	Interactive image;
	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]

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.

[1] 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.

[pmid27398024-2] 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.

[3] 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.

[4] 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.

[5] 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.

[1]

[2]

[3]

[4]

[5]

See also

References