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From the plant

CBCNCannabichromanone

A trace C20 cannabinoid with a chromanone nucleus and no established origin; no known affinity for the cannabinoid receptors.

Unscheduled
Level of detail

C₂₀H₂₈O₄

CID 25105340

Family
PhytocannabinoidMinor
Origin
Origin not established
Molar mass
332.40 g/mol

Updated on

In plain terms

Cannabichromanone is a very rare cannabinoid, found first in hashish in 1975 and then in THC-rich cannabis flowers. How it forms is unknown. No study has measured its action at the cannabinoid receptors.

Receptors and activity

    Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

    Measured effects

    Not characterised. No placebo-controlled human trial has measured the effects of CBCN, so no level is shown.

    Levels computed from placebo-controlled human trials: difference from placebo on 100, at the dose and route stated. Read the method

    Pharmacology

    Cannabichromanone (CBCN) was described in 1975 by Friedrich-Fiechtl and Spiteller in Afghan hashish, then re-isolated in 2008 from the flowering tops of high-Δ9-THC cannabis by Ahmed et al., who named it cannabichromanone A and described three new derivatives, cannabichromanones B, C and D. Its chroman-4-one nucleus carries a 3-oxobutyl chain and has twenty carbons instead of the usual twenty-one; the stereocentre at 3 is (S). Its origin, enzymatic or by degradation, is not established. No affinity for the CB1 or CB2 receptors has been measured. In the only published screen (Ahmed 2008), the four cannabichromanones showed no antimicrobial activity; cannabichromanone A weakly inhibited Plasmodium falciparum in vitro (IC50 of 3.7 and 3.8 µg/mL depending on the strain), the four compounds had moderate activity against Leishmania (IC50 of 9.0 to 14.0 µg/mL), and all gave a strong signal in a qualitative DPPH plate test.

    Key sources.

    History

    Source
    Isolated from hashish (1975) and then from high-Δ9-THC cannabis (2008); origin not established

    Biosynthetic pathway

    No formation pathway, enzymatic or not, has been established; no source consulted links it to an oxidation of CBC.

    Classification

    Family, origin and source verification

    Family

    Phytocannabinoid › Minor

    Presence in the plant

    Present in the plant; origin not established

    Chemistry

    Miscellaneous · C5 side chain · neutral form

    Verification

    Every fact on this entry was checked against its primary sources on 20 October 2026.

    Wikipedia (English)

    No dedicated article.

    References

    1. Friedrich-Fiechtl & Spiteller 1975, Tetrahedron 31:479: « Neue Cannabinoide 1 » (new tab)DOI 10.1016/0040-4020(75)85016-2
    2. Ahmed et al. 2008, Tetrahedron Lett 49:6050: cannabichromanones A to D, absolute configuration and screening (new tab)PMID 19844597
    3. Radwan et al. 2021, Molecules: « miscellaneous » cannabinoids (new tab)PMID 34066753
    4. Lewis et al. 2017, ACS Omega: profiling of cannabis extracts (m/z 329 signal) (new tab)PMID 30023762
    5. PubChem CID 25105340: (3S)-cannabichromanone (new tab)
    6. ANSM, consolidated list of narcotics, updated 26/06/2026 (new tab)

    Identifiers

    Names

    Common name
    Cannabichromanone
    IUPAC name
    (3S)-5-hydroxy-2,2-dimethyl-3-(3-oxobutyl)-7-pentyl-3H-chromen-4-one
    Other names
    cannabichromanone A · CBCN-C5

    Identifiers

    Formula
    C₂₀H₂₈O₄
    PubChem CID
    25105340(new tab)
    InChIKey
    NHZMSIOYBVIOAF-OAHLLOKOSA-N
    SMILES
    CCCCCC1=CC(=C2C(=C1)OC([C@@H](C2=O)CCC(=O)C)(C)C)O

    Machine-readable entry (JSON)

    LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.