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;
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;

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]

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. S2CID 256792029.
^ US 2008/0176885, 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 (2011). "Improving the Use of Drug Combination through the Codrug Approach". In Rautio J (ed.). Prodrugs and Targeted Delivery: Towards Better ADME Properties. Wiley. pp. 345–383 (374–376). ISBN 978-3-527-63318-0.

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[pmid36825573-1] 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. S2CID 256792029.

[2] US 2008/0176885, 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 (2011). "Improving the Use of Drug Combination through the Codrug Approach". In Rautio J (ed.). Prodrugs and Targeted Delivery: Towards Better ADME Properties. Wiley. pp. 345–383 (374–376). ISBN 978-3-527-63318-0.

[1]

[2]

[3]

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
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

Cod-THC

See also

References