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Minor phytocannabinoid

Unscheduled

CBLCannabicyclol

Aliases.CBL · Cannabicyclol

A UV degradation product of CBC. A marker of the age / oxidation of flower.

Updated on

Level of detail

Identifiers

Formula
C₂₁H₃₀O₂
Molar mass
314.46 g·mol⁻¹
CAS
21366-63-2
PubChem CID
59444380
First described
1964
Origin
Plant (photochemical product)
InChIKey
IGHTZQUIFGUJTG-QSMXQIJUSA-N

In plain terms

CBL is what forms when sunlight degrades CBC in the flower. It is an oxidation marker: its presence indicates poorly stored or old flower.

Receptors and activity

  • CB1
    Modulator
  • CB2
    Modulator
  • 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
    20
  • Clarity
    25
  • Sleep
    15
  • Appetite
    10
  • High
    5

Editorial estimate, not clinical.

Pharmacology

CBL (cannabicyclol) was described by Korte & Sieper (1964) and then structurally characterised by Crombie & Ponsford (1968). There is no enzymatic biosynthesis: it is a product of photo-induced [2+2] cyclisation of CBC under UV light. Practically absent from fresh plant material, it accumulates in aged and poorly stored flower (an oxidation marker). Pharmacology: negligible CB1/CB2 activity, no psychotropic effect reported. Caprioglio et al. (Biomolecules 2022, PMID 36008978) place it within the "dark cannabinome". Its molar mass is identical to that of CBD (314.46 g·mol⁻¹) and so is its molecular formula, C₂₁H₃₀O₂, but its cyclic skeleton distinguishes it unambiguously in chromatography (HPLC, GC-MS). In practice, a high CBL level in an extract signals advanced photochemical degradation of the source plant material.

Biosynthetic pathway

Photochemical product of the UV degradation of CBC; no known enzymatic pathway

Structural classification

Class
Minor phytocannabinoid
Origin
Plant (photochemical product)
Status
Unscheduled

References

  1. 1.Caprioglio · Biomolecules 2022PMID 36008978

Structured data

InChIKey
IGHTZQUIFGUJTG-QSMXQIJUSA-N
SMILES
CCCCCC1=CC(=C2[C@@H]3[C@H]4[C@@H](C3(C)C)CC[C@]4(OC2=C1)C)O
Formula
C21H30O2
Molar mass
314.46 g·mol⁻¹
CAS
21366-63-2
PubChem CID
59444380
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