cannabichromene

Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene, is a phytocannabinoid, one of the hundreds of cannabinoids found in the Cannabis plant. It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others. It is not scheduled by the Convention on Psychotropic Substances.

Chemical data

Formula: C21H30O2
Molecular weight: 314.5 g/mol
IUPAC name: 2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromen-5-ol
SMILES: CCCCCC1=CC(=C2C=CC(OC2=C1)(C)CCC=C(C)C)O
InChIKey: UVOLYTDXHDXWJU-UHFFFAOYSA-N
XLogP: 6.9
Polar surface area: 29.5 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

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Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 314.225

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chemical formula: C₂₁H₃₀O₂
canonical SMILES: CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1)O
found in taxon: Cannabis sativa

Sources (2)

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Encyclopedic overview

3 sections

Contents

Biosynthesis
Pharmacology
References

== Biosynthesis == Within the Cannabis plant, CBC occurs mainly as cannabichromenic acid (CBCA, 2-COOH-CBC, CBC-COOH). Geranyl pyrophosphate and olivetolic acid combine to produce cannabigerolic acid (CBGA; the sole intermediate for all other phytocannabinoids), which is cyclized by the enzyme CBCA synthase to form CBCA. Over time, or when heated above 93 °C, CBCA is decarboxylated, producing CBC. See also the biosynthetic scheme image below. class=skin-invert-image|thumb|600px|left|CBC biosynthetic scheme

Excerpted from Wikipedia’s “cannabichromene” article, available under the CC BY-SA 4.0 licence.

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