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Canna·wiki3'-OH-THC

Semi-synthetic cannabinoid

Narcotic: generic clause

3'-OH-THC3'-Hydroxy-Δ9-tetrahydrocannabinol

(6aR,10aR)-3-(3-hydroxypentyl)-6,6,9-triméthyl-6a,7,8,10a-tétrahydrobenzo[c]chromén-1-ol

Aliases.3'-hydroxy-THC · 3'-OH-Δ9-THC · 3'-hydroxy-Δ9-tétrahydrocannabinol

A THC metabolite oxidised on the side chain; its S enantiomer is more potent than THC itself.

Updated on

Level of detail

Harm-reduction warning

No characterised human dose: animal / in vitro data only. Effect profile, safety margin and acute toxicity are not documented in human clinical practice. Extremely potent compound: severe effects, seizures and deaths reported in the literature.

Identifiers

Formula
C₂₁H₃₀O₃
Molar mass
330.50 g·mol⁻¹
CAS
-
PubChem CID
101594562
Origin
No natural occurrence in the plant. The molecule forms in the body as a phase I metabolite of Δ9-THC, by a parallel and minority route relative to hydroxylation at position 11. The two enantiomers were prepared separately in the laboratory for the purposes of pharmacological study.
InChIKey
GWSPOZKXWMVVEN-YJEKIOLLSA-N

In plain terms

3'-hydroxy-THC is a metabolite of THC whose oxidation falls on the side chain rather than on the top of the molecule. Two mirror-image forms of it exist, and one of the two proves more active than the starting THC. It is a study molecule, never a consumer product.

Receptors and activity

  • CB1
    Agonist
  • CB2
    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
    40
  • Clarity
    15
  • Sleep
    50
  • Appetite
    55
  • High
    65

Editorial estimate, not clinical.

Pharmacology

3'-hydroxy-Δ9-tetrahydrocannabinol is a phase I metabolite of Δ9-THC arising from oxidation of the pentyl chain, a parallel and minority route relative to the hydroxylation at position 11 that produces 11-OH-THC. Its pharmacological interest rests entirely on its stereochemistry. Creation of an asymmetric centre on the third carbon of the side chain generates two enantiomers, and Martin and colleagues showed in 1984 that these two forms do not have the same potency: the S isomer clearly exceeds the R isomer on murine hypoactivity, canine static ataxia and generalisation in drug discrimination in rats, and it even surpasses reference Δ9-THC on those three measures. The authors' conclusion has remained a structuring argument of cannabinoid pharmacology: the metabolism of THC is not a simple inactivation process, it can produce compounds more active than the parent molecule, and the conformation of the side chain constitutes a structural requirement in its own right for behavioural activity. The fact that the same pair of enantiomers behaves identically on hypothermia moreover indicates that the various cannabinoid effects do not all depend on the same conformational constraints.

Key sources.

Route of preparation (chemical process)

There is no plant route for this molecule. It forms by microsomal hydroxylation of the third carbon of the pentyl chain of Δ9-THC, under the action of hepatic cytochromes P450. That side-chain oxidation coexists with allylic hydroxylation at position 11 and with deeper oxidative cleavages of the same chain, which produce a family of shortened metabolites.

Structural classification

Class
Semi-synthetic cannabinoid
Origin
No natural occurrence in the plant. The molecule forms in the body as a phase I metabolite of Δ9-THC, by a parallel and minority route relative to hydroxylation at position 11. The two enantiomers were prepared separately in the laboratory for the purposes of pharmacological study.
Status
Narcotic: generic clause

References

  1. 1.Martin et coll. 1984 : puissance pharmacologique comparée des énantiomères R et S du 3'-hydroxy-Δ9-THCPMID 6087379
  2. 2.Harvey et Brown 1989 : coupure oxydative de la chaîne pentyle des cannabinoïdes et nouvelles voies de biotransformationPMID 2559552

Structured data

InChIKey
GWSPOZKXWMVVEN-YJEKIOLLSA-N
SMILES
CCC(CCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O)O
Formula
C21H30O3
Molar mass
330.50 g·mol⁻¹
PubChem CID
101594562
Machine-readable entry (JSON)

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