WIN 55,212-2

[(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

Overview

WIN 55,212-2 belongs to Cannabinoids.

Key safety note: WIN 55,212-2 is a research chemical, not a medicine or a quality-controlled consumer product, and there is essentially no human safety data.[2]
Effects
Subjective effects vary. What a substance feels like depends on dose, individual physiology, mindset, and setting. The points below describe commonly reported effects, not guaranteed, uniform, or desirable outcomes.
  • In animal models: the full 'cannabinoid tetrad', analgesia, lowered body temperature, catalepsy and reduced movement, more potent than THC.
  • Predicted human effects (from the related full-agonist 'Spice/K2' synthetic cannabinoids): intense intoxication, anxiety or panic, rapid heartbeat and possible psychosis.
  • No characterised or safe human dose.
Dosing & duration
Harm-reduction note: These are commonly cited reference ranges, not a recommendation or a “safe” dose. Potency, purity, body chemistry, tolerance, and drug combinations vary widely. Start low, go slow, wait for full effects before redosing, and never assume an unknown product matches these figures. Missing data is not evidence of safety.

Used as a laboratory reagent (dissolved for in-vitro and animal studies). There is no established or safe human dose. Figures for human use do not exist.. WIN 55,212-2 is a research chemical with no validated human use. There is no known safe dose or route, as a high-efficacy CB1 full agonist it would be expected to carry the acute risks of the 'Spice/K2' synthetic cannabinoids (severe intoxication, psychosis, seizures, cardiac events).

Dose ranges

Duration

Chemical & Physical Properties
FormulaC27H26N2O3
Molar mass426.5 g/mol
StateSolid (usually the mesylate salt, white to off-white crystalline powder)
Melting pointunavailable: true. reason: no reliable experimental melting point is reported for this research chemical (free base or mesylate salt)
Boiling pointNot reported
DensityNot reported
Vapor pressureNot reported
pKaNot reported
LogP4.4 (predicted, XLogP3, free base)
SolubilityMesylate salt: soluble in DMSO and ethanol. Sparingly soluble in water (research-reagent solvents)
Refractive indexNot reported
Identifiers & Synonyms
CAS131543-22-1
CAS (enantiomer)
PubChem CID5311501
InChIKeyHQVHOQAKMCMIIM-HXUWFJFHSA-N
InChIInChI=1S/C27H26N2O3/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28/h2-11,20H,12-17H2,1H3/t20-/m1/s1
SMILESCC1=C(C2=C3N1[C@@H](COC3=CC=C2)CN4CCOCC4)C(=O)C5=CC=CC6=CC=CC=C65

Synonyms

    Pharmacodynamics & Biochemistry

    WIN 55,212-2 is a synthetic cannabinoid of the aminoalkylindole class: structurally unrelated to THC, yet a potent full agonist at both cannabinoid receptors. It activates CB1 (Kᵢ ≈16 nM) and CB2 (Kᵢ ≈1 nM) with higher affinity than THC and, unlike THC's partial agonism, produces the full receptor response, so in animals it reproduces and exceeds the classic cannabinoid effects (analgesia, hypothermia, catalepsy, reduced movement). It also has documented secondary actions, including subunit-specific modulation of glycine receptors and agonism at the PPARα/γ nuclear receptors. Its activity is strongly stereospecific: the name 'WIN 55,212-2' refers specifically to the active (R)-(+) enantiomer, while the mirror-image (S)-(−) enantiomer, 'WIN 55,212-3', is essentially inactive at cannabinoid receptors. That clean enantiomer split made it a key pharmacological tool for showing that cannabinoid effects are receptor-mediated. WIN 55,212-2 is one of the most widely used cannabinoid research compounds, employed to probe CB1/CB2 signalling, analgesia and neuroprotection. Its aminoalkylindole/naphthoylindole chemistry also historically inspired the naphthoylindole 'Spice/K2' synthetic cannabinoids that later appeared as drugs of misuse, though WIN 55,212-2 itself is a laboratory reagent rather than a street product.

    Biological targets

    • CB1
    • CB2

    Binding & functional measurements

    TargetMeasurementSpecies
    CB1 receptorEC50 284 nMHuman
    CB2 receptorEC50 62 nMHuman
    Pharmacokinetics
    BioavailabilityNot reported
    TmaxNot reported
    Half-lifeNot established in humans (research compound)
    VdNot reported
    Protein bindingNot reported
    MetabolismHepatic (animal studies)
    ExcretionNot reported
    Toxicology & Safety
    Harm-reduction note: Toxicity and risk depend on dose, route, purity, combinations, setting, and individual health factors. Missing harms should never be interpreted as evidence of safety.

    Not reported

    WIN 55,212-2 is a research chemical, not a medicine or a quality-controlled consumer product, and there is essentially no human safety data. As a high-affinity FULL agonist at CB1 (more efficacious than THC), it would be expected to produce intense and potentially dangerous cannabinoid effects: severe intoxication, anxiety and panic, tachycardia and other cardiovascular effects, sedation, and psychotomimetic reactions: of the kind seen with the related 'Spice/K2' full-agonist synthetic cannabinoids, which have caused seizures, acute psychosis and deaths. Because it is sold only as a laboratory reagent, its dose, purity and effects in humans are uncharacterised, and there is no safe recreational use. It should be handled as a potent bioactive research chemical.[2]

    Legal Status
    Legal note: Legal status can change over time and may vary by country, region, formulation, analogue status, prescription context, and enforcement practice. Always confirm with current official sources before relying on this section.
    Interactions & Contraindications

    Drug interactions

    Cannabis, Alcohol As a CB1/CB2 full agonist it is additive with other cannabinoids and, like the 'Spice' cannabinoids, potentially with CNS depressants, but no human interaction data exist.[2]

    Contraindications

    Research chemical with no safety data (not for human consumption) a laboratory reagent with no safety data and no established safe dose or route.[2]
    Personal or family history of psychosis, schizophrenia or bipolar disorder high-efficacy synthetic cannabinoids can trigger psychosis, seizures and cardiac events.[2]
    Usage & Context
    • A laboratory research tool: one of the most widely used synthetic cannabinoids for studying CB1/CB2 receptor pharmacology, signalling, analgesia and neuroprotection.
    • Its aminoalkylindole/naphthoylindole chemistry influenced the later 'Spice/K2' synthetic cannabinoids that became drugs of misuse, though WIN 55,212-2 itself is a reagent, not a consumer product.
    • No approved medical use.
    Sources & Evidence

    Further Information