WIN 55,212-2
A laboratory full agonist at CB1 and CB2, classified as a narcotic in France, with no human data.
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.
C₂₇H₂₆N₂O₃
CAS 131543-22-1
- Family
- Synthetic CB receptor agonistResearch ligand or medicine
- Molar mass
- 426.50 g/mol
Updated on
In plain terms
WIN 55,212-2 is a laboratory molecule with no link to hemp: it was made by chemists and described in 1992. It binds to the same receptors as THC, more strongly than THC. It serves as a research tool and has never been a consumer product; in France, it is named on the list of narcotics.
Receptors and activity
Target network
- Activates
- Blocks or inhibits
The lower the cited value, the closer the target sits to WIN 55,212-2: 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 WIN 55,212-2.
CB1CB1 found in 7 regions of the body
- Basal gangliadenseMost dense in basal ganglia outflow nuclei1
- CerebellumdenseVery dense in the cerebellum1
- HippocampusdenseVery high concentrations in the hippocampus2
- AmygdaladenseHigh concentrations in the amygdala2
- CortexpresentPresent throughout the neocortex2
- Adipose tissuepresentExpressed in adipose tissue3
- GutpresentColonic epithelium, smooth muscle and plexus4
Map sources
- Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
- Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
- Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
- Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)
Cited values
- CB1Agonistno measured value cited
- CB2Agonistno measured value cited
- TRPV1Inhibitorno measured value cited
- PPARαAgonistno measured value cited
Pharmacology
The lead aminoalkylindole, WIN 55,212-2 is a reference cannabinoid agonist in the laboratory. Chemically foreign to plant cannabinoids, it nevertheless fully activates CB1 and CB2: the IUPHAR review reports affinities of 1.89 to 123 nM at CB1 and 0.28 to 16.2 nM at CB2, with an intrinsic activity comparable to that of CP55940 and HU-210 (Pertwee et al., Pharmacol Rev 2010, PMID 21079038). In mice, the (+) enantiomer reproduced the effects of THC (reduced locomotion, hypothermia, antinociception, immobility) and produced a THC-like discriminative stimulus in rats, whereas the (−) enantiomer was inactive (Compton et al. 1992). Targets outside the cannabinoid system are documented: inhibition of TRPV1 through a calcineurin-dependent route (Patwardhan et al. 2006) and binding to PPARα (Sun et al. 2007); GPR55 is not affected. No clinical trial, pharmacokinetic or metabolism data in humans were found. In mice, sub-chronic administration at low doses produced a dose-dependent anxiogenic effect and a fall in locomotor activity, with minimal histological changes (Omran et al. 2023); any extrapolation to humans remains unfounded.
Key sources.
- Pertwee RG et al., Pharmacol Rev 2010 (IUPHAR): cannabinoid receptors and their ligands (new tab)PMID 21079038
- D'Ambra TE et al., J Med Chem 1992: constrained analogues of pravadoline, aminoalkylindole agonists of the cannabinoid receptor (new tab)PMID 1732519
- Compton DR et al., J Pharmacol Exp Ther 1992: cannabimimetic activity of aminoalkylindoles (new tab)PMID 1335057
- Patwardhan AM et al., Proc Natl Acad Sci USA 2006: WIN 55,212-2 inhibits TRPV1 via calcineurin (new tab)PMID 16849427
- Sun Y et al., Br J Pharmacol 2007: activation of PPARα by cannabinoids (new tab)PMID 17906680
- Omran GA et al., BMC Pharmacol Toxicol 2023: toxicity profiles of subchronic WIN55,212-2 administration in mice (new tab)PMID 36750905
- ANSM, consolidated list of substances classified as narcotics (updated 16/02/2026): WIN 55,212-2 listed in annex IV (new tab)
History
- Source
- An entirely synthetic molecule, absent from cannabis and from every living organism. It was born in a pharmaceutical laboratory, through chemical modification of pravadoline, an indole derivative developed as an anti-inflammatory. The prefix WIN refers to the Sterling Winthrop laboratory, where the series was developed. It has never been marketed as a medicine and circulates only as a research reagent and as an analytical standard.
Origin
Laboratory synthesis
No biosynthetic pathway: the molecule is produced by no plant and no organism. It is a synthetic molecule of the aminoalkylindole class, whose R configuration is the one that carries the activity.
Legal framework
- European Union
No European Union classification measure was found in the sources consulted; the status depends on the national law of each Member State. France classifies it by name as a narcotic.
- France
Classified as a narcotic in France, and by name: the consolidated list of substances classified as narcotics published by the ANSM (updated 16/02/2026) explicitly cites WIN 55,212-2 in Annex IV, with the reference to the order of 14 October 2019 amending the order of 22 February 1990. It is therefore not caught by the generic clause on tetrahydrocannabinols: the molecule is not a tetrahydrocannabinol and is covered in its own right. It falls under the narcotics regime.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Classification
Family, origin and source verification
- Family
Synthetic CB receptor agonist › Research ligand or medicine
- Class
aminoalkylindole
- Verification
Classification, sources and binding values checked on 20 October 2026; text read against its sources and Wikipedia.
- Wikipedia (English)
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
- Pertwee RG et al., Pharmacol Rev 2010 (IUPHAR): cannabinoid receptors and their ligands (new tab)PMID 21079038
- D'Ambra TE et al., J Med Chem 1992: constrained analogues of pravadoline, aminoalkylindole agonists of the cannabinoid receptor (new tab)PMID 1732519
- Compton DR et al., J Pharmacol Exp Ther 1992: cannabimimetic activity of aminoalkylindoles (new tab)PMID 1335057
- Patwardhan AM et al., Proc Natl Acad Sci USA 2006: WIN 55,212-2 inhibits TRPV1 via calcineurin (new tab)PMID 16849427
- Sun Y et al., Br J Pharmacol 2007: activation of PPARα by cannabinoids (new tab)PMID 17906680
- Omran GA et al., BMC Pharmacol Toxicol 2023: toxicity profiles of subchronic WIN55,212-2 administration in mice (new tab)PMID 36750905
- ANSM, consolidated list of substances classified as narcotics (updated 16/02/2026): WIN 55,212-2 listed in annex IV (new tab)
Identifiers
Names
- IUPAC name
- [(11R)-2-methyl-11-(morpholin-4-ylmethyl)-9-oxa-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7-tetraen-3-yl]-naphthalen-1-ylmethanone
- Other names
- WIN 55212-2 · R-(+)-WIN 55,212-2
Identifiers
- Formula
- C₂₇H₂₆N₂O₃
- CAS
- 131543-22-1
- PubChem CID
- 5311501(new tab)
- InChIKey
- HQVHOQAKMCMIIM-HXUWFJFHSA-N
- SMILES
- CC1=
C(C2= C3N1[C@@H] (COC3= CC= C2) CN4CCOCC4) C(= O) C5= CC= CC6= CC= CC= C65
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.