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CB-25

Synthetic CB1 and CB2 ligand with a partial or inverse profile at CB1, used as a research tool.

Unscheduled
Level of detail

C₂₅H₄₁NO₃

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.

Data sheet

Names

IUPAC name
N-cyclopropyl-11-(3-hydroxy-5-pentylphenoxy)undecanamide
Other names
CCG-208736 · DB-221616 · NS00017326 · orb1944655

Identifiers

Formula
C₂₅H₄₁NO₃
Molar mass
403.60 g/mol
PubChem CID
11654304(new tab)
InChIKey
XFHZHCKWTBGPFD-UHFFFAOYSA-N

Class

Family
ECS modulator (research)

Legal status

Status
Unscheduled
See the legal framework

Updated on

Receptors and activity

  1. CB1Partial agonist90 out of 100

    Ki 5,2 nM sur CB1 humain exprimé dans des cellules COS (Brizzi et coll., 2005)

  2. CB2Antagonist84 out of 100

    Ki 13,0 nM sur CB2 humain exprimé dans des cellules COS (Brizzi et coll., 2005) ; antagonisme neutre fonctionnel (Cascio et coll., 2006)

Bar length shows the relative strength of the interaction, as an indication.

Subjective signature

Calm
5 out of 100
Relaxation of body and mind; reduced mental noise without marked drowsiness.
Clarity
2 out of 100
Sustained attention and clear thinking; functional lucidity, not euphoria.
High
2 out of 100
Euphoria and sensory intensity; altered perception of time and space.
Appetite
2 out of 100
Stimulation of hunger and of taste appreciation (the “munchies” effect).
Sleep
3 out of 100
Sedative effect: aids sleep onset and the continuity of deep sleep.
Editorial estimate, not clinical.

Pharmacology

CB-25 is a synthetic ligand of the cannabinoid receptors CB1 and CB2, described in 2005 by Brizzi et al. in the Journal of Medicinal Chemistry. The original study reports a Ki of 5.2 nM at CB1 and 13.0 nM at CB2 in human receptors, with affinity constants clearly lower than those of anandamide. In functional tests, it behaves mainly as a partial agonist of CB1 on mouse brain membranes, and as an inverse agonist in a cyclic AMP test on N18TG2 cells. At CB2, it behaves as a neutral antagonist (Cascio et al., 2006). In rodents, it produces dose-dependent nociception in healthy rats and attenuates both phases of the formalin test in mice. No human data are published in the sources consulted.

Key sources.

History

Source
A fully synthetic molecule. No plant source is reported in the sources consulted. It belongs to the series of ligands derived from olivetol and resorcinol, which combines a 5-pentylresorcinol core, one hydroxyl of which is etherified, with an alkyloxy chain ending in an N-cyclopropyl amide.

Origin (research tool)

No biosynthetic pathway. The molecule is a chemical synthesis product belonging to the family of olivetol-type alkylated resorcinols. No living organism is reported to produce it in the sources consulted.

References

  1. Brizzi A et coll., conception, synthèse et études de liaison de nouveaux ligands des récepteurs cannabinoïdes, J Med Chem 2005 (new tab)PMID 16279794
  2. Cascio MG et coll., pharmacologie in vitro et in vivo de ligands cannabinoïdes synthétiques dérivés de l'olivétol ou du résorcinol, Br J Pharmacol 2006 (new tab)PMID 16953186
  3. ChEMBL, fiche du composé CHEMBL225506 (constantes Ki sur CB1 et CB2 humains, document CHEMBL1139484) (new tab)
  4. PubChem, notice du composé CB-25 (CID 11654304) (new tab)
  5. ANSM, liste consolidée des substances classées comme stupéfiants (mise à jour du 16 février 2026) (new tab)
  6. INCB, Liste verte 2026 (substances des Conventions de 1961 et 1971) (new tab)

Structured data

SMILES
CCCCCC1=CC(=CC(=C1)OCCCCCCCCCCC(=O)NC2CC2)O
InChIKey
XFHZHCKWTBGPFD-UHFFFAOYSA-N

Machine-readable entry (JSON)

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