Cannabis Ruderalis

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Cannabicitran
Identifiers
  • 1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.04,13.07,12]pentadeca-7(12),8,10-triene
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
  • CCCCCc1cc2O[C@@]3(C)C[C@H]4c2c(c1)OC(C)(C)[C@H]4CC3
  • InChI=1S/C21H30O2/c1-5-6-7-8-14-11-17-19-15-13-21(4,23-18(19)12-14)10-9-16(15)20(2,3)22-17/h11-12,15-16H,5-10,13H2,1-4H3
  • Key:IXJXRDCCQRZSDV-UHFFFAOYSA-N

Cannabicitran (CBTC) is a phytocannabinoid first isolated in 1974 as a trace component of Cannabis sativa,[1][2][3][4] and also found in some other plants.[5][6] It is not psychoactive, but was found to reduce intraocular pressure in tests on rabbits,[7] which may reflect agonist activity at the NAGly receptor (formally GPR18) that is known to be a target of many structurally related cannabinoids.[8]

See also

References

  1. ^ Bercht CAL, et al. Cannabicitran: A new naturally occurring tetracyclic diether from lebanese Cannabis sativa. Phytochemistry 1974; 13(3): 619-621. doi:10.1016/S0031-9422(00)91362-1
  2. ^ Ross SA, ElSohly MA, Sultana GN, Mehmedic Z, Hossain CF, Chandra S. Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L. Phytochem Anal. 2005 Jan-Feb;16(1):45-8. doi:10.1002/pca.809 PMID 15688956
  3. ^ Radwan MM, Chandra S, Gul S, ElSohly MA. Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis. Molecules. 2021 May 8;26(9):2774. doi:10.3390/molecules26092774 PMID 34066753
  4. ^ Hanuš LO, Meyer SM, Muñoz E, Taglialatela-Scafati O, Appendino G (November 2016). "Phytocannabinoids: a unified critical inventory". Natural Product Reports. 33 (12): 1357–1392. doi:10.1039/c6np00074f. PMID 27722705.
  5. ^ Lee YR, Kim JH. Efficient Synthesis of Polycycles by Electrocyclizations of Substituted Trihydroxybenzenes: Synthesis of Rubranine and Deoxybruceol. Synlett 2007; 14: 2232-2236. doi:10.1055/s-2007-985562
  6. ^ Iwata N, Kitanaka S. New cannabinoid-like chromane and chromene derivatives from Rhododendron anthopogonoides. Chem Pharm Bull (Tokyo). 2011;59(11):1409-12. doi:10.1248/cpb.59.1409 PMID 22041081
  7. ^ ElSohly MA, Harland EC, Benigni DA, Waller CW. Cannabinoids in glaucoma II: the effect of different cannabinoids on intraocular pressure of the rabbit. Curr Eye Res. 1984 Jun;3(6):841-50. doi: 10.3109/02713688409000797. PMID: 6329602
  8. ^ Caldwell MD, Hu SS, Viswanathan S, Bradshaw H, Kelly ME, Straiker A (June 2013). "A GPR18-based signalling system regulates IOP in murine eye". British Journal of Pharmacology. 169 (4): 834–43. doi:10.1111/bph.12136. PMC 3687663. PMID 23461720.
source: https://en.wikipedia.org/w/index.php?title=Cannabicitran&oldid=1047286145

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