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{{Short description|Chemical compound}} |
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{{Drugbox |
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| IUPAC_name = 1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0<sup>4,13</sup>.0<sup>7,12</sup>]pentadeca-7(12),8,10-triene |
| IUPAC_name = 1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0<sup>4,13</sup>.0<sup>7,12</sup>]pentadeca-7(12),8,10-triene |
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'''Cannabicitran''' ('''CBTC''') is a [[phytocannabinoid]] first isolated in 1974 as a trace component of ''[[Cannabis sativa]]'',<ref>{{cite journal | vauthors = Bercht CL, Lousberg RJ, Küppers FJ, Salemink CA | title = Cannabicitran: a new naturally occurring tetracyclic diether from Lebanese Cannabis sativa. | journal = Phytochemistry | date = March 1974 | volume = 13 | issue = 3 | pages = 619–21 | doi = 10.1016/S0031-9422(00)91362-1 }}</ref><ref>{{cite journal | vauthors = Ross SA, ElSohly MA, Sultana GN, Mehmedic Z, Hossain CF, Chandra S | title = Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L | journal = Phytochemical Analysis | year = 2005 | volume = 16 | issue = 1 | pages = 45–8 | pmid = 15688956 | doi = 10.1002/pca.809 }}</ref><ref>{{cite journal | vauthors = Radwan MM, Chandra S, Gul S, ElSohly MA | title = Cannabinoids, Phenolics, Terpenes and Alkaloids of ''Cannabis'' | journal = Molecules | volume = 26 | issue = 9 | date = May 2021 | page = 2774 | pmid = 34066753 | doi = 10.3390/molecules26092774 | pmc = 8125862 | doi-access = free }}</ref><ref name="pmid27722705">{{cite journal | vauthors = Hanuš LO, Meyer SM, Muñoz E, Taglialatela-Scafati O, Appendino G | title = Phytocannabinoids: a unified critical inventory | journal = Natural Product Reports | volume = 33 | issue = 12 | pages = 1357–1392 | date = November 2016 | pmid = 27722705 | doi = 10.1039/c6np00074f }}</ref> Structurally related compounds can be found in some other plants.<ref>{{cite journal | vauthors = Lee YR, Kim JH | title = Efficient Synthesis of Polycycles by Electrocyclizations of Substituted Trihydroxybenzenes: Synthesis of Rubranine and Deoxybruceol. | journal = Synlett | date = 2007 | volume = 2007 | issue = 14 | pages = 2232–2236 | doi = 10.1055/s-2007-985562}}</ref><ref>{{cite journal | vauthors = Iwata N, Kitanaka S | title = New cannabinoid-like chromane and chromene derivatives from Rhododendron anthopogonoides | journal = Chemical & Pharmaceutical Bulletin | year = 2011 | volume = 59 | issue = 11 | pages = 1409–12 | pmid = 22041081 | doi = 10.1248/cpb.59.1409 | doi-access = free }}</ref> It is not psychoactive, but was found to reduce [[intraocular pressure]] in tests on rabbits,<ref name="pmid6329602">{{cite journal | vauthors = ElSohly MA, Harland EC, Benigni DA, Waller CW | title = Cannabinoids in glaucoma II: the effect of different cannabinoids on intraocular pressure of the rabbit | journal = Current Eye Research | volume = 3 | issue = 6 | pages = 841–50 | date = June 1984 | pmid = 6329602 | doi = 10.3109/02713688409000797 }}</ref> which may reflect agonist activity at the [[NAGly receptor]] (formally GPR18) that is known to be a target of many structurally related cannabinoids.<ref name="pmid23461720">{{cite journal | vauthors = Caldwell MD, Hu SS, Viswanathan S, Bradshaw H, Kelly ME, Straiker A | title = A GPR18-based signalling system regulates IOP in murine eye | journal = British Journal of Pharmacology | volume = 169 | issue = 4 | pages = 834–43 | date = June 2013 | pmid = 23461720 | pmc = 3687663 | doi = 10.1111/bph.12136 }}</ref> |
'''Cannabicitran''' ('''CBTC''') is a [[phytocannabinoid]] first isolated in 1974 as a trace component of ''[[Cannabis sativa]]'',<ref>{{cite journal | vauthors = Bercht CL, Lousberg RJ, Küppers FJ, Salemink CA | title = Cannabicitran: a new naturally occurring tetracyclic diether from Lebanese Cannabis sativa. | journal = Phytochemistry | date = March 1974 | volume = 13 | issue = 3 | pages = 619–21 | doi = 10.1016/S0031-9422(00)91362-1 }}</ref><ref>{{cite journal | vauthors = Ross SA, ElSohly MA, Sultana GN, Mehmedic Z, Hossain CF, Chandra S | title = Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L | journal = Phytochemical Analysis | year = 2005 | volume = 16 | issue = 1 | pages = 45–8 | pmid = 15688956 | doi = 10.1002/pca.809 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Radwan MM, Chandra S, Gul S, ElSohly MA | title = Cannabinoids, Phenolics, Terpenes and Alkaloids of ''Cannabis'' | journal = Molecules | volume = 26 | issue = 9 | date = May 2021 | page = 2774 | pmid = 34066753 | doi = 10.3390/molecules26092774 | pmc = 8125862 | doi-access = free }}</ref><ref name="pmid27722705">{{cite journal | vauthors = Hanuš LO, Meyer SM, Muñoz E, Taglialatela-Scafati O, Appendino G | title = Phytocannabinoids: a unified critical inventory | journal = Natural Product Reports | volume = 33 | issue = 12 | pages = 1357–1392 | date = November 2016 | pmid = 27722705 | doi = 10.1039/c6np00074f | doi-access = free }}</ref> Structurally related compounds can be found in some other plants.<ref>{{cite journal | vauthors = Lee YR, Kim JH | title = Efficient Synthesis of Polycycles by Electrocyclizations of Substituted Trihydroxybenzenes: Synthesis of Rubranine and Deoxybruceol. | journal = Synlett | date = 2007 | volume = 2007 | issue = 14 | pages = 2232–2236 | doi = 10.1055/s-2007-985562}}</ref><ref>{{cite journal | vauthors = Iwata N, Kitanaka S | title = New cannabinoid-like chromane and chromene derivatives from Rhododendron anthopogonoides | journal = Chemical & Pharmaceutical Bulletin | year = 2011 | volume = 59 | issue = 11 | pages = 1409–12 | pmid = 22041081 | doi = 10.1248/cpb.59.1409 | doi-access = free }}</ref> It is not psychoactive, but was found to reduce [[intraocular pressure]] in tests on rabbits,<ref name="pmid6329602">{{cite journal | vauthors = ElSohly MA, Harland EC, Benigni DA, Waller CW | title = Cannabinoids in glaucoma II: the effect of different cannabinoids on intraocular pressure of the rabbit | journal = Current Eye Research | volume = 3 | issue = 6 | pages = 841–50 | date = June 1984 | pmid = 6329602 | doi = 10.3109/02713688409000797 }}</ref> which may reflect agonist activity at the [[NAGly receptor]] (formally GPR18) that is known to be a target of many structurally related cannabinoids.<ref name="pmid23461720">{{cite journal | vauthors = Caldwell MD, Hu SS, Viswanathan S, Bradshaw H, Kelly ME, Straiker A | title = A GPR18-based signalling system regulates IOP in murine eye | journal = British Journal of Pharmacology | volume = 169 | issue = 4 | pages = 834–43 | date = June 2013 | pmid = 23461720 | pmc = 3687663 | doi = 10.1111/bph.12136 }}</ref> |
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== See also == |
== See also == |
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* [[Cannabimovone]] |
* [[Cannabimovone]] |
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* [[Cannabitriol]] |
* [[Cannabitriol]] |
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* [[Isotetrahydrocannabinol]] |
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== References == |
== References == |
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Latest revision as of 16:43, 14 December 2023
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| Formula | C21H30O2 |
| Molar mass | 314.469 g·mol−1 |
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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[edit]
- 9-OH-HHC
- Cannabichromene
- Cannabicyclol
- Cannabidiol dimethyl ether
- Cannabielsoin
- Cannabigerol
- Cannabimovone
- Cannabitriol
- Isotetrahydrocannabinol
References[edit]
- ^ 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.