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PL Cannabinoid · Synthetic (research chemical)
WIN-55,212-2 is a fully synthetic aminoalkylindole cannabinoid used as a laboratory research agonist, and like other synthetic cannabinoids it is potent, unpredictable and linked to serious harm.
Where it fits
WIN-55,212-2 derives from Synthetic. See the Synthetic & altered cannabinoids index for how it relates to the rest of the family.
What the research shows
Direct human research on WIN-55,212-2 is minimal; it is characterised mainly by its chemistry and its place in the cannabinoid family rather than by clinical studies. We flag that plainly rather than overstate it.
Safety
A fully synthetic cannabinoid, covered for education and harm reduction only. Synthetic cannabinoids are potent, unpredictable and linked to serious harm and deaths. No synthesis, dose or source information appears on this site.
Aminoalkylindole Chemistry and CB1/CB2 Receptor Pharmacology
WIN-55,212-2 (molecular formula C27H26N2O3, molecular weight 426.51 g/mol) is a conformationally restrained aminoalkylindole synthesized by D'Ambra and colleagues at Sterling-Winthrop Research Institute in 1992 from pravadoline (WIN-48,098) templates. Although structurally unrelated to classical dibenzopyran phytocannabinoids like delta-9-THC, the (+)-enantiomer WIN-55,212-2 binds with high nanomolar affinity to both CB1 (Ki ~ 1.9 nM) and CB2 (Ki ~ 0.28 nM) receptors as a full efficacy agonist, whereas its (-)-enantiomer (WIN-55,212-3) is pharmacologically inactive (D'Ambra et al., 1992). In preclinical rodent bioassays, WIN-55,212-2 reproduces the complete cannabinoid tetrad (hypolocomotion, antinociception, hypothermia, and catalepsy) with higher potency than delta-9-THC (Compton et al., 1992; Huffman et al., 1996).
Sources
- D'Ambra TE, Estep KG, Bell MR, et al. (1992). Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor. Journal of Medicinal Chemistry, 35(1), 124-135. PMID 1732519
- Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (1992). Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol. Journal of Pharmacology and Experimental Therapeutics, 263(3), 1118-1126. PMID 1335057
- Huffman JW, Yu S, Showalter V, et al. (1996). Synthesis and pharmacology of a very potent cannabinoid lacking a phenolic hydroxyl with high affinity for the CB2 receptor. Journal of Medicinal Chemistry, 39(20), 3875-3877. PMID 8831752
FAQ
Is WIN-55,212-2 intoxicating? Yes. Unlike delta-9-THC (a partial CB1 agonist), WIN-55,212-2 is a potent full agonist at central CB1 receptors and produces strong cannabimimetic effects.
Where does WIN-55,212-2 come from? WIN-55,212-2 is a fully synthetic aminoalkylindole developed in 1992 at Sterling-Winthrop Research Institute and does not occur naturally in the Cannabis sativa plant.
Why is WIN-55,212-2 used alongside WIN-55,212-3 in laboratory pharmacology? Receptor binding is strictly stereoselective: the (+)-isomer WIN-55,212-2 activates CB1 and CB2 receptors at nanomolar concentrations, whereas the (-)-enantiomer WIN-55,212-3 is inactive and serves as a negative control.
Part of the NOIDS cannabinoids index. Educational reference, not medical advice.
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