Cannabicitran

Cannabicitran
Identifiers
	IUPAC name 1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.04,13.07,12]pentadeca-7(12),8,10-triene;
CAS Number	19352-64-8 ; 31508-71-1;
PubChem CID	59444393;
ChemSpider	58828773;
CompTox Dashboard (EPA)	DTXSID10953497 ;
Chemical and physical data
Formula	C21H30O2
Molar mass	314.469 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCc1cc2O[C@@]3(C)C[C@H]4c2c(c1)OC(C)(C)[C@H]4CC3;
	InChI 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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[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.

[pmid27722705-4] 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.

[pmid6329602-7] 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.

[pmid23461720-8] 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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Identifiers


IUPAC name 1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0^4,13.0^7,12]pentadeca-7(12),8,10-triene
CAS Number	19352-64-8^Y 31508-71-1
PubChem CID	59444393
ChemSpider	58828773
CompTox Dashboard (EPA)	DTXSID10953497
Chemical and physical data
Formula	C₂₁H₃₀O₂
Molar mass	314.469 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCc1cc2O[C@@]3(C)C[C@H]4c2c(c1)OC(C)(C)[C@H]4CC3
InChI 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

See also

References