Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H26N2O3 |
| Molecular Weight | 426.5069 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(C(=O)C2=C3C=CC=CC3=CC=C2)C4=C5N1[C@H](CN6CCOCC6)COC5=CC=C4
InChI
InChIKey=HQVHOQAKMCMIIM-HXUWFJFHSA-N
InChI=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
| Molecular Formula | C27H26N2O3 |
| Molecular Weight | 426.5069 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/7565624https://www.ncbi.nlm.nih.gov/pubmed/25874692 | https://www.ncbi.nlm.nih.gov/pubmed/22634229 | https://www.ncbi.nlm.nih.gov/pubmed/11399676 | https://www.ncbi.nlm.nih.gov/pubmed/11168547Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/9121688 | https://www.ncbi.nlm.nih.gov/pubmed/15728830 | https://www.ncbi.nlm.nih.gov/pubmed/11168547
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7565624https://www.ncbi.nlm.nih.gov/pubmed/25874692 | https://www.ncbi.nlm.nih.gov/pubmed/22634229 | https://www.ncbi.nlm.nih.gov/pubmed/11399676 | https://www.ncbi.nlm.nih.gov/pubmed/11168547
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/9121688 | https://www.ncbi.nlm.nih.gov/pubmed/15728830 | https://www.ncbi.nlm.nih.gov/pubmed/11168547
WIN 55212-2 is the synthetic cannabimimetic compound. It is a potent aminoalkylindole cannabinoid receptor agonist. WIN 55,212-2 increases expression of anti-oxidant Cu/Zn SOD and is able to prevent inflammation induced by Aβ1-42 in cultured astrocytes. It exerts neuroprotective and anti-inflammatory actions against Aβ damage through both CB₁ and CB₂ receptors. WIN 55212-2 attenuates hyperalgesia and allodynia in a rat model of neuropathic pain. In the clinical trial, it was revealed that WIN 55212-2, applied topically, decreases the intraocular pressure of human glaucoma resistant to conventional therapies within the first 30 min.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL218 |
93.0 nM [Ki] | ||
Target ID: WP195 |
|||
Target ID: CHEMBL253 |
3.3 nM [Ki] | ||
Target ID: CHEMBL218 |
24.0 nM [IC50] | ||
Target ID: CHEMBL253 |
0.41 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Endocannabinoids suppress excitatory synaptic transmission to dorsal raphe serotonin neurons through the activation of presynaptic CB1 receptors. | 2009-10 |
|
| Neurochemical evidence that stimulation of CB1 cannabinoid receptors on GABAergic nerve terminals activates the dopaminergic reward system by increasing dopamine release in the rat nucleus accumbens. | 2009-06 |
|
| Cannabinoid CB1 and cholecystokinin CCK2 receptors modulate, in an opposing way, electrically evoked [3H]GABA efflux from rat cerebral cortex cell cultures: possible relevance for cortical GABA transmission and anxiety. | 2009-05 |
|
| Gz mediates the long-lasting desensitization of brain CB1 receptors and is essential for cross-tolerance with morphine. | 2009-03-10 |
|
| Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats. | 2009-01 |
|
| Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine. | 2008-10-15 |
|
| Mapping the structural requirements in the CB1 cannabinoid receptor transmembrane helix II for signal transduction. | 2008-04 |
|
| Role of cannabinoid CB1 receptors and Gi/o protein activation in the modulation of synaptosomal Na+,K+-ATPase activity by WIN55,212-2 and delta(9)-THC. | 2007-10-15 |
|
| Long-term reduction of brain-derived neurotrophic factor levels and signaling impairment following prenatal treatment with the cannabinoid receptor 1 receptor agonist (R)-(+)-[2,3-dihydro-5-methyl-3-(4-morpholinyl-methyl) pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1- naphthalenylmethanone. | 2007-06 |
|
| Cannabinoids excite hypothalamic melanin-concentrating hormone but inhibit hypocretin/orexin neurons: implications for cannabinoid actions on food intake and cognitive arousal. | 2007-05-02 |
|
| CB1 receptor activation in the basolateral amygdala produces antinociception in animal models of acute and tonic nociception. | 2007-04-19 |
|
| Anti-inflammatory property of the cannabinoid agonist WIN-55212-2 in a rodent model of chronic brain inflammation. | 2007-02-23 |
|
| R-(+)-[2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl)-pyrrolo-[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphtalenylmethanone (WIN-2) ameliorates experimental autoimmune encephalomyelitis and induces encephalitogenic T cell apoptosis: partial involvement of the CB(2) receptor. | 2006-12-15 |
|
| Neuropathic pain and the endocannabinoid system in the dorsal raphe: pharmacological treatment and interactions with the serotonergic system. | 2006-10 |
|
| Evaluation of the role of nicotinic acetylcholine receptor subtypes and cannabinoid system in the discriminative stimulus effects of nicotine in rats. | 2006-07-01 |
|
| Cannabinoid receptor type 1 located on presynaptic terminals of principal neurons in the forebrain controls glutamatergic synaptic transmission. | 2006-05-24 |
|
| Periaqueductal grey CB1 cannabinoid and metabotropic glutamate subtype 5 receptors modulate changes in rostral ventromedial medulla neuronal activities induced by subcutaneous formalin in the rat. | 2005 |
|
| Retroinhibition of presynaptic Ca2+ currents by endocannabinoids released via postsynaptic mGluR activation at a calyx synapse. | 2004-06-30 |
|
| Cannabinoid receptor type 1 modulates excitatory and inhibitory neurotransmission in mouse colon. | 2004-01 |
|
| Long-term effects on cortical glutamate release induced by prenatal exposure to the cannabinoid receptor agonist (R)-(+)-[2,3-dihydro-5-methyl-3-(4-morpholinyl-methyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenylmethanone: an in vivo microdialysis study in the awake rat. | 2004 |
|
| Functional tolerance and blockade of long-term depression at synapses in the nucleus accumbens after chronic cannabinoid exposure. | 2003-06-15 |
|
| Milk intake and survival in newborn cannabinoid CB1 receptor knockout mice: evidence for a "CB3" receptor. | 2003-02-07 |
|
| The heritability of antinociception: common pharmacogenetic mediation of five neurochemically distinct analgesics. | 2003-02 |
|
| The rodent amygdala contributes to the production of cannabinoid-induced antinociception. | 2003 |
|
| N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A) interaction with LYS 3.28(192) is crucial for its inverse agonism at the cannabinoid CB1 receptor. | 2002-12 |
|
| Effects of Win 55,212-2 on hippocampal CA1 long-term potentiation in experiments controlled for basal glutamatergic synaptic transmission. | 2002-10-25 |
|
| Desensitization of cannabinoid-mediated presynaptic inhibition of neurotransmission between rat hippocampal neurons in culture. | 2002-03 |
|
| Assessment of the role of CB1 receptors in cannabinoid anticonvulsant effects. | 2001-09-28 |
|
| Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. | 1996-09 |
|
| Molecular cloning, expression and function of the murine CB2 peripheral cannabinoid receptor. | 1996-06-07 |
|
| Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. | 1995-09 |
|
| Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids. | 1993-03 |
|
| Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol. | 1992-12 |
|
| Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor. | 1992-01 |
Sample Use Guides
Radioligand binding studies were performed using male Sprague-Dawley rat cerebellar membranes from a 48,000 x g pellet which was washed twice by suspension in 20 mM HEPES buffer, pH 7. The final assay volume was 1 ml and included: 20 mM HEPES, pH 7; 0.5 nM [3H]-(R)-(+)-WIN 55212-2 (specific activity 59 Ci/mmOl, Dupont NEN); 1 mg/ml BSA; 100-120 ug cerebellar membrane protein and varying concentrations of competing compounds. WIN 55212-2 appeared to bind to a single class of sites (Kd = 2 nM: Bmax = 1.2 pmoles/mg protein) and was saturable, heat-labile, reversible and stereospecific.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:57:48 GMT 2025
by
admin
on
Mon Mar 31 21:57:48 GMT 2025
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| Record UNII |
5H31GI9502
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| Record Status |
Validated (UNII)
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| Record Version |
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WIKIPEDIA |
Designer-drugs-WIN-55212-2
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DB13950
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5H31GI9502
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131543-22-1
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DTXSID40894849
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5311501
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131513-18-3
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NON-SPECIFIC STEREOCHEMISTRY | |||
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WIN 55,212-2
Created by
admin on Mon Mar 31 21:57:48 GMT 2025 , Edited by admin on Mon Mar 31 21:57:48 GMT 2025
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PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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TARGET -> AGONIST |
BINDING
IC50
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TARGET -> AGONIST |
Mouse AtT-20 neuroblastoma cells stably transfected with human CB2
EC50
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TARGET -> AGONIST |
BINDING
IC50
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
Mouse AtT-20 neuroblastoma cells stably transfected with human CB1
EC50
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LABELED -> NON-LABELED |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
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