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Tetrahydrocannabiorcol

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Tetrahydrocannabiorcol
Identifiers
  • (6aR,10aR)-3,6,6,9-tetramethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC17H22O2
Molar mass258.361 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 aphytocannabinoid found inCannabis pollen.[1] It is ahomologue ofTHC andTHCV with thealkyl side chain replaced by a smallermethyl group. Unlike THC and THCV, THCC has negligible affinity for the CB1 and CB2cannabinoid 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 theTRPA1 calcium channel which plays an important role inpain perception,[2] and it has been shown to produceanalgesic effects via activation of spinal TRPA1 channels.[3][4] THCC was studied byRoger Adams as early as 1942.[5]

See also

[edit]

References

[edit]
  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.
  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.
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