THC-O-phosphate

THC-O-phosphate is a water-soluble organophosphate ester derivative of tetrahydrocannabinol (THC), which functions as a metabolic prodrug for THC itself. It was invented in 1978 in an attempt to get around the poor water solubility of THC and make it easier to inject for the purposes of animal research into its pharmacology and mechanism of action. The main disadvantage of THC phosphate ester is the slow rate of hydrolysis of the ester link, resulting in delayed onset of action and lower potency than the parent drug. Pharmacologically, it is comparable to the action of psilocybin as a metabolic prodrug for psilocin.

THC-O-phosphate
Skeletal formula of THC-O-phosphate
Space-filling model of the THC-O-phosphate molecule
Identifiers
  • O-Phosphoryl-Δ8-tetrahydrocannabinol
PubChem CID
ChemSpider
Chemical and physical data
FormulaC21H31O5P
Molar mass394.448 g·mol−1
3D model (JSmol)
  • OP(O)(=O)Oc3cc(CCCCC)cc2OC(C)(C)C1C\C=C(\C)CC1c23
  • InChI=1S/C21H31O5P/c1-5-6-7-8-15-12-18-20(19(13-15)26-27(22,23)24)16-11-14(2)9-10-17(16)21(3,4)25-18/h9,12-13,16-17H,5-8,10-11H2,1-4H3,(H2,22,23,24) checkY
  • Key:SVDBVZOOOSEJCD-UHFFFAOYSA-N checkY
  (verify)

THC phosphate ester is made by reacting THC with phosphoryl chloride using pyridine as a solvent, following by quenching with water to produce THC phosphate ester. In the original research the less active but more stable isomer Δ8-THC was used, but the same reaction scheme could be used to make the phosphate ester of the more active isomer Δ9-THC.[1]

See also

References
  1. Yoshimura H, Watanabe K, Oguri K, Fujiwara M, Ueki S (October 1978). "Synthesis and pharmacological activity of a phosphate ester of delta8-tetrahydrocannabinol". Journal of Medicinal Chemistry. 21 (10): 1079–81. doi:10.1021/jm00208a014. PMID 569207.
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