Content deleted Content added
Vanished user 0x8cSXE0x6 (talk | contribs) No edit summary |
→top: formatting |
||
| (7 intermediate revisions by 5 users not shown) | |||
| Line 1: | Line 1: | ||
{{Short description|Chemical compound}} |
|||
{{Drugbox |
{{Drugbox |
||
| Watchedfields = changed |
| Watchedfields = changed |
||
| Line 33: | Line 34: | ||
}} |
}} |
||
'''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 |
'''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 |
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|Δ<sup>8</sup>-THC]] was used, but the same reaction scheme could be used to make the phosphate ester of the more active isomer Δ<sup>9</sup>-THC.<ref>{{cite journal | vauthors = Yoshimura H, Watanabe K, Oguri K, Fujiwara M, Ueki S | title = Synthesis and pharmacological activity of a phosphate ester of delta8-tetrahydrocannabinol | journal = Journal of Medicinal Chemistry | volume = 21 | issue = 10 | pages = 1079–81 | date = October 1978 | pmid = 569207 | doi = 10.1021/jm00208a014 }}</ref> |
||
==See also== |
|||
* [[THC-O-acetate]] |
|||
* [[THC hemisuccinate]] |
|||
* [[THC morpholinylbutyrate]] |
|||
== References == |
== References == |
||
| Line 42: | Line 48: | ||
{{cannabinoids}} |
{{cannabinoids}} |
||
[[Category:Benzochromenes]] |
|||
[[Category:Cannabinoids]] |
[[Category:Cannabinoids]] |
||
[[Category:Phosphate esters]] |
[[Category:Phosphate esters]] |
||
Revision as of 00:54, 28 December 2023
 | |
 | |
| Identifiers | |
|---|---|
| |
| PubChem CID | |
| ChemSpider | |
| Chemical and physical data | |
| Formula | C21H31O5P |
| Molar mass | 394.448 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
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.[1]
See also
References
- ^ 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.