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THC-O-phosphate
Sign in to save'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 metabo
In the Vinony graph
Vinony's link graph records 447 inbound references to THC-O-phosphate, and connects out to JWH-210, synhexyl and digital object identifier.
It is catalogued under topics including Benzochromenes, Cannabinoids and Chemical pages without DrugBank identifier.
Vinony links it to 4 Wikipedia language editions.
Chemical data
- Formula
- C21H31O5P
- Molecular weight
- 394.4 g/mol
- IUPAC name
- [(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl] dihydrogen phosphate
- SMILES
- CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)OP(=O)(O)O
- InChIKey
- PXBRWSCGFNNIKS-IAGOWNOFSA-N
- XLogP
- 5.7
- Polar surface area
- 76 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 394.19091072199996
Show 4 more facts
- chemical formula
- C₂₁H₃₁O₅P
- canonical SMILES
- CCCCCC1=CC2=C(C3C=C(CCC3C(O2)(C)C)C)C(=C1)OP(=O)(O)O
- Commons category
- THC-O-phosphate
- isomeric SMILES
- CCCCCc1cc2c(c(OP(=O)(O)O)c1)[C@@H]1C=C(C)CC[C@H]1C(C)(C)O2
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Encyclopedic overview
2 sectionsContents
- See also
- References
'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 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.
Excerpted from Wikipedia’s “THC-O-phosphate” article, available under the CC BY-SA 4.0 licence.