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Canna·wikiTHC-O-phosphate

Semi-synthetic cannabinoid

Narcotic: generic clause

THC-O-phosphateΔ9-tetrahydrocannabinol phosphate

[(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl] dihydrogen phosphate

Aliases.THC-O-phosphate · phosphate de THC · THC phosphate ester · Δ9-THC-O-phosphate

A water-soluble phosphoric ester of THC, a prodrug limited by difficult hydrolysis.

Updated on

Level of detail

Identifiers

Formula
C₂₁H₃₁O₅P
Molar mass
394.40 g·mol⁻¹
CAS
-
PubChem CID
9865413
Origin
A semi-synthetic compound, absent from cannabis. It results from phosphorylation of the phenol of tetrahydrocannabinol, an operation that introduces a strongly ionisable and therefore water-soluble group. It has no commercial existence and belongs to the field of research.
InChIKey
PXBRWSCGFNNIKS-IAGOWNOFSA-N

In plain terms

THC phosphate is THC made soluble in water by the addition of a phosphate group. The idea was that it would turn back into THC in the body, but that transformation happens badly: the product remains far less active than the original molecule.

Receptors and activity

  • CB1
    Partial agonist
  • CB2
    Partial agonist
  • Agonist
  • Partial agonist
  • Antagonist
  • Modulator
  • Inverse agonist

Hover over a row for the precise value (Ki, EC50…)

Subjective signature

Hover over an axis to read its definition.

  • Calm
    35
  • Clarity
    15
  • Sleep
    55
  • Appetite
    40
  • High
    30

Editorial estimate, not clinical.

Pharmacology

Tetrahydrocannabinol phosphate is a water-soluble prodrug obtained by phosphorylation of the phenol of THC, on the model of psilocybin, itself the phosphoric ester of an active compound. The analogy stops at the structure, however. Yoshimura and colleagues (1978), who carried out that work on the ester of Δ8-THC, found that the phosphate hydrolyses only with difficulty, both by alkaline phosphatase and by a mouse liver homogenate, which compromises the very principle of the prodrug. The pharmacological profile bears the trace of this: the cataleptogenic effect and the potentiation of thiopental sleep in mice represented only about ten and seven per cent of those of Δ8-THC, while the hypothermic effect retained comparable potency with a longer duration. Acute toxicity was by contrast far lower than that of the parent compound. The present entry describes the ester of Δ9-THC, obtained by the same scheme; the pharmacological data cited come from the Δ8 series and are transposable to it only with caution.

Key sources.

Route of preparation (chemical process)

No plant route. The compound is the phosphoric ester of Δ9-THC: the phenol function at position 1 of the benzo[c]chromene skeleton bears a dihydrogen phosphate group. It is that group, ionised at physiological pH, which confers water solubility. The molecule is described here by chemical class only.

Structural classification

Class
Semi-synthetic cannabinoid
Origin
A semi-synthetic compound, absent from cannabis. It results from phosphorylation of the phenol of tetrahydrocannabinol, an operation that introduces a strongly ionisable and therefore water-soluble group. It has no commercial existence and belongs to the field of research.
Status
Narcotic: generic clause

References

  1. 1.Yoshimura et coll. 1978 : synthèse et activité pharmacologique d'un ester phosphate du Δ8-THCPMID 569207
  2. 2.PubChem CID 9865413 : ester phosphorique du tétrahydrocannabinol

Structured data

InChIKey
PXBRWSCGFNNIKS-IAGOWNOFSA-N
SMILES
CCCCCc1cc2c(c(OP(=O)(O)O)c1)[C@@H]1C=C(C)CC[C@H]1C(C)(C)O2
Formula
C21H31O5P
Molar mass
394.40 g·mol⁻¹
PubChem CID
9865413
Machine-readable entry (JSON)

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