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From the plant

Cannabicitran

A racemic tetracyclic diether of cannabis, up to about 10% of some CBD extracts.

FranceNarcotic: generic clauseInternationalUnscheduled
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.

C₂₁H₃₀O₂

CAS 19352-64-8

Family
PhytocannabinoidMinor
Origin
Degradation product (debated)
Molar mass
314.50 g/mol

Updated on

In plain terms

Cannabicitran is a rare cannabinoid of cannabis. It is found mainly in some purified CBD extracts, where it can reach about 10%, and its racemic form suggests it forms at least partly without an enzyme. Its effects in the body have barely been studied.

Receptors and activity

Target network

TRPV1Modulatorno measured value
  • Blocks or inhibits
  • Binds or modulates

The lower the cited value, the closer the target sits to Cannabicitran: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of Cannabicitran.

Brain, side view
Body, front view
Blood

TRPV1TRPV1 found in 7 regions of the body

  1. Sensory gangliapresentExpressed in dorsal root ganglia1
  2. Spinal cordpresentNerve fibres in the spinal dorsal horn2
  3. CortexpresentParietal cortex neurons (layers 3 and 5)3
  4. SkinpresentWidely distributed in the skin4
  5. Blood vesselspresentPresent on dermal blood vessels4
  6. BonepresentPresent on osteoclasts5
  7. LiverpresentRNA enriched in the liver6

Map sources

  1. Cortright DN et al. The tissue distribution and functional characterization of human VR1. Biochem Biophys Res Commun, 2001 (new tab)
  2. Facer P et al. Differential expression of the capsaicin receptor TRPV1 and related novel receptors TRPV3, TRPV4 and TRPM8 in normal human tissues and changes in traumatic and diabetic neuropathy. BMC Neurol, 2007 (new tab)
  3. Mezey E et al. Distribution of mRNA for vanilloid receptor subtype 1 (VR1), and VR1-like immunoreactivity, in the central nervous system of the rat and human. Proc Natl Acad Sci U S A, 2000 (new tab)
  4. Ständer S et al. Expression of vanilloid receptor subtype 1 in cutaneous sensory nerve fibers, mast cells, and epithelial cells of appendage structures. Exp Dermatol, 2004 (new tab)
  5. Rossi F et al. The endovanilloid/endocannabinoid system in human osteoclasts: possible involvement in bone formation and resorption. Bone, 2009 (new tab)
  6. Human Protein Atlas. TRPV1 tissue expression (RNA consensus) (new tab)

Cited values

  1. TRPV1Modulatorno measured value cited
  2. AChEInhibitorno measured value cited
  3. BChEInhibitorno measured value cited
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.

Pharmacology

Cannabicitran is a tetracyclic cannabinoid of the « miscellaneous » class: its benzo[c]chromene nucleus is fully saturated on the terpene ring and the phenolic oxygen is engaged in an ether bridge, so it has no free hydroxyl. Synthesised in 1971 (« citrylidene-cannabis ») and isolated in 1974 from Lebanese cannabis, it proved racemic in 2023 (Wood), which casts doubt on an enzymatic origin; it can make up about 10% of some purified CBD extracts and was isolated from a commercial Δ8-THC distillate (Radwan 2023). No affinity for CB1 or CB2 has been measured, the only mention of CB2 coming from a docking calculation. In cultured rat sensory neurons it blocked the capsaicin response in 35.2 ± 16.5% of neurons, the lowest score of the ten minor cannabinoids compared (Anand 2025); at 200 µM it inhibited acetylcholinesterase by 66.0% and butyrylcholinesterase by 77.0%. No human data exist. In France its structure appears to fall within the generic benzo[c]chromene class scheduled in June 2024, a reading a lawyer must confirm.

Key sources.

History

Source
Present in cannabis, probably as a transformation product (origin debated): identified in Lebanese hashish and then in pollen, it can reach about 10% of some so-called purified CBD extracts and was isolated from a commercial Δ8-THC distillate. Its racemic nature casts doubt on an enzymatic origin.

Biosynthetic pathway

No enzyme is known. Cannabicitran extracted from Cannabis sativa is racemic, which casts doubt on its long-presumed enzymatic origin; Wood and colleagues (2023) discuss several scenarios for the formation of the racemate, in the plant and/or during extract processing, without settling the question.

Classification

Family, origin and source verification

Family

Phytocannabinoid › Minor

Presence in the plant

Artefact: formed by oxidation, light, heat or solvent

Sources disagree on this point.

Chemistry

Miscellaneous · C5 side chain · neutral form

Verification

Checked on 20 October 2026; some points still await human review.

Wikipedia (English)

Cannabicitran (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

References

  1. Wood et al. 2023, Chirality: natural cannabicitran is racemic (new tab)PMID 37142400
  2. Wood et al. 2022, Magn Reson Chem: 1H and 13C NMR assignments; up to ~10% of purified CBD extracts (new tab)PMID 34617621
  3. Bercht et al. 1974, Phytochemistry 13:619: isolation from a Lebanese cannabis (new tab)DOI 10.1016/S0031-9422(00)91362-1
  4. ElSohly & Slade 2005, Life Sci: synthesis 1971 (« citrylidene-cannabis »), isolation 1974 (new tab)PMID 16199061
  5. Ross et al. 2005, Phytochem Anal: cannabinoids of Cannabis sativa pollen (new tab)PMID 15688956
  6. Radwan et al. 2023, J Nat Prod: impurities in commercial Δ8-THC products (new tab)PMID 36827690
  7. Anand et al. 2025, J Pain Res: ten minor cannabinoids on sensitised neurons (new tab)PMID 41322279
  8. Puopolo et al. 2022, Med Cannabis Cannabinoids: cholinesterase inhibition (new tab)PMID 35702400
  9. Van Niekerk et al. 2026, J Cannabis Res: CB2 docking and ex vivo nasal permeation (new tab)PMID 41992383
  10. Gul et al. 2023, Planta Med: validated GC-FID method for 20 cannabinoids (new tab)PMID 36257598
  11. Radwan et al. 2021, Molecules: « miscellaneous » class (new tab)PMID 34066753
  12. ANSM, consolidated list of narcotics (updated 26/06/2026) and decisions of 22/05/2024 and 03/06/2024 (benzo[c]chromene class) (new tab)
  13. PubChem CID 59444393: cannabicitran, undefined stereochemistry (new tab)

Identifiers

Names

IUPAC name
1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.04,13.07,12]pentadeca-7(12),8,10-triene
Other names
CBTC · (±)-cannabicitran · Citrylidenecannabis · Cannabicitrane · CBCT

Identifiers

Formula
C₂₁H₃₀O₂
CAS
19352-64-8
PubChem CID
59444393(new tab)
InChIKey
IXJXRDCCQRZSDV-UHFFFAOYSA-N
SMILES
CCCCCC1=CC2=C3C4CC(CCC4C(O2)(C)C)(OC3=C1)C

Machine-readable entry (JSON)

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