Cod-THC

Cod-THC
Identifiers
	IUPAC name [(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] [(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl] carbonate;
PubChem CID	143656467;
Chemical and physical data
Formula	C40H49NO6
Molar mass	639.833 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CC[C@@]23c4c5C[C@@H]1[C@@H]2C=C[C@H](OC(=O)Oc1cc(CCCCC)cc2OC(C)(C)[C@@H]6CCC(C)=C[C@H]6c21)[C@@H]3Oc4c(OC)cc5;
	InChI InChI=InChI=1S/C40H49NO6/c1-7-8-9-10-24-20-32(34-26-19-23(2)11-13-27(26)39(3,4)47-33(34)21-24)45-38(42)44-31-16-14-28-29-22-25-12-15-30(43-6)36-35(25)40(28,37(31)46-36)17-18-41(29)5/h12,14-16,19-21,26-29,31,37H,7-11,13,17-18,22H2,1-6H3/t26-,27-,28+,29-,31+,37+,40+/m1/s1; Key:VDTVNOCXWSYPQX-IWHNUUHWSA-N;

Cod-THC (Codeine Δ⁹-tetrahydrocannabinol carbonate) is a synthetic codrug formed by linking tetrahydrocannabinol with codeine via a carbonate bridge. It is well absorbed orally and shows superior analgesic effects in animal studies compared to a simple mixture of the two drugs.^[1]^[2]^[3]

THC can partially inhibit CYP2D6, which is the enzyme that transforms codeine into its active metabolite morphine.^[4]^[5] It's not well understood how THC may impact codeines metabolism in humans.

References

↑ Banerjee A, Hayward JJ, Trant JF (May 2023). ""Breaking bud": the effect of direct chemical modifications of phytocannabinoids on their bioavailability, physiological effects, and therapeutic potential". Organic & Biomolecular Chemistry. 21 (18): 3715–3732. doi:10.1039/d3ob00068k. PMID 36825573.
↑ US 2008176885A1, Holtman JR, Crooks PA, Dhooper HK, "Novel synergistic opioid-cannabinoid codrug for pain management", published 24 July 2008, assigned to University of Kentucky and Insys Therapeutics Inc
↑ Crooks PA, Dhooper HK, Chakraborty U (2010). "Improving the Use of Drug Combinations Through the Codrug Approach". Prodrugs and Targeted Delivery. Methods and Principles in Medicinal Chemistry. Vol. 47. pp. 345–383. doi:10.1002/9783527633166.ch13. ISBN 978-3-527-32603-7.
↑ Nasrin S, Watson CJ, Perez-Paramo YX, Lazarus P (December 2021). "Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions". Drug Metabolism and Disposition. 49 (12): 1070–1080. doi:10.1124/dmd.121.000442. PMC 11022895. PMID 34493602.
↑ Huff HC, Vasan A, Roy P, Kaul A, Tajkhorshid E, Das A (September 2021). "Differential Interactions of Selected Phytocannabinoids with Human CYP2D6 Polymorphisms". Biochemistry. 60 (37): 2749–2760. doi:10.1021/acs.biochem.1c00158. PMC 8455456. PMID 34491040.

[Banerjee_2023-1] Banerjee A, Hayward JJ, Trant JF (May 2023). ""Breaking bud": the effect of direct chemical modifications of phytocannabinoids on their bioavailability, physiological effects, and therapeutic potential". Organic & Biomolecular Chemistry. 21 (18): 3715–3732. doi:10.1039/d3ob00068k. PMID 36825573.

[2] US 2008176885A1, Holtman JR, Crooks PA, Dhooper HK, "Novel synergistic opioid-cannabinoid codrug for pain management", published 24 July 2008, assigned to University of Kentucky and Insys Therapeutics Inc

[3] Crooks PA, Dhooper HK, Chakraborty U (2010). "Improving the Use of Drug Combinations Through the Codrug Approach". Prodrugs and Targeted Delivery. Methods and Principles in Medicinal Chemistry. Vol. 47. pp. 345–383. doi:10.1002/9783527633166.ch13. ISBN 978-3-527-32603-7.

[4] Nasrin S, Watson CJ, Perez-Paramo YX, Lazarus P (December 2021). "Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions". Drug Metabolism and Disposition. 49 (12): 1070–1080. doi:10.1124/dmd.121.000442. PMC 11022895. PMID 34493602.

[5] Huff HC, Vasan A, Roy P, Kaul A, Tajkhorshid E, Das A (September 2021). "Differential Interactions of Selected Phytocannabinoids with Human CYP2D6 Polymorphisms". Biochemistry. 60 (37): 2749–2760. doi:10.1021/acs.biochem.1c00158. PMC 8455456. PMID 34491040.

[1]

[2]

[3]

[4]

[5]

See also

References