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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
ChemSpider
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] Structurally related compounds can be 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 CL, Lousberg RJ, Küppers FJ, Salemink CA (March 1974). "Cannabicitran: a new naturally occurring tetracyclic diether from Lebanese Cannabis sativa". Phytochemistry. 13 (3): 619–21. doi: 10.1016/S0031-9422(00)91362-1.
  2. ^ 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. doi: 10.1002/pca.809. PMID  15688956.
  3. ^ Radwan MM, Chandra S, Gul S, ElSohly MA (May 2021). "Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis". Molecules. 26 (9): 2774. doi: 10.3390/molecules26092774. PMC  8125862. 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 (2007). "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 (2011). "New cannabinoid-like chromane and chromene derivatives from Rhododendron anthopogonoides". Chemical & Pharmaceutical Bulletin. 59 (11): 1409–12. doi: 10.1248/cpb.59.1409. PMID  22041081.
  7. ^ ElSohly MA, Harland EC, Benigni DA, Waller CW (June 1984). "Cannabinoids in glaucoma II: the effect of different cannabinoids on intraocular pressure of the rabbit". Current Eye Research. 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.


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