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Cannabicitran

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
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 aphytocannabinoid first isolated in 1974 as a trace component ofCannabis 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 reduceintraocular pressure in tests on rabbits,[7] which may reflect agonist activity at theNAGly receptor (formally GPR18) that is known to be a target of many structurally related cannabinoids.[8]

See also

[edit]

References

[edit]
  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 ofCannabis".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.hdl:10668/10523.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.
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-3-tetrahydrocannabinols
Delta-4-tetrahydrocannabinols
Delta-7-tetrahydrocannabinols
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Delta-11-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers
(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)


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