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=CC=CC3=C2C=CC=C3)C4=CC=CC5=C4N1[C@H](CN6CCOCC6)CO5
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 |
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.
Originator
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] |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. | 1995 Sep |
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| Molecular cloning, expression and function of the murine CB2 peripheral cannabinoid receptor. | 1996 Jun 7 |
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| Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. | 1996 Sep |
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| Assessment of the role of CB1 receptors in cannabinoid anticonvulsant effects. | 2001 Sep 28 |
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| 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 Dec |
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| Desensitization of cannabinoid-mediated presynaptic inhibition of neurotransmission between rat hippocampal neurons in culture. | 2002 Mar |
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| Effects of Win 55,212-2 on hippocampal CA1 long-term potentiation in experiments controlled for basal glutamatergic synaptic transmission. | 2002 Oct 25 |
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| The rodent amygdala contributes to the production of cannabinoid-induced antinociception. | 2003 |
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| Milk intake and survival in newborn cannabinoid CB1 receptor knockout mice: evidence for a "CB3" receptor. | 2003 Feb 7 |
|
| Functional tolerance and blockade of long-term depression at synapses in the nucleus accumbens after chronic cannabinoid exposure. | 2003 Jun 15 |
|
| 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 |
|
| Cannabinoid receptor type 1 modulates excitatory and inhibitory neurotransmission in mouse colon. | 2004 Jan |
|
| Retroinhibition of presynaptic Ca2+ currents by endocannabinoids released via postsynaptic mGluR activation at a calyx synapse. | 2004 Jun 30 |
|
| 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 |
|
| 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 Dec 15 |
|
| Evaluation of the role of nicotinic acetylcholine receptor subtypes and cannabinoid system in the discriminative stimulus effects of nicotine in rats. | 2006 Jul 1 |
|
| Cannabinoid receptor type 1 located on presynaptic terminals of principal neurons in the forebrain controls glutamatergic synaptic transmission. | 2006 May 24 |
|
| Neuropathic pain and the endocannabinoid system in the dorsal raphe: pharmacological treatment and interactions with the serotonergic system. | 2006 Oct |
|
| Anti-inflammatory property of the cannabinoid agonist WIN-55212-2 in a rodent model of chronic brain inflammation. | 2007 Feb 23 |
|
| 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 Jun |
|
| Cannabinoids excite hypothalamic melanin-concentrating hormone but inhibit hypocretin/orexin neurons: implications for cannabinoid actions on food intake and cognitive arousal. | 2007 May 2 |
|
| CB1 receptor activation in the basolateral amygdala produces antinociception in animal models of acute and tonic nociception. | 2007 May-Jun |
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| 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 Oct 15 |
|
| Mapping the structural requirements in the CB1 cannabinoid receptor transmembrane helix II for signal transduction. | 2008 Apr |
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| Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine. | 2008 Oct 15 |
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| Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats. | 2009 Jan |
|
| 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 Jun |
|
| Gz mediates the long-lasting desensitization of brain CB1 receptors and is essential for cross-tolerance with morphine. | 2009 Mar 10 |
|
| 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 May |
|
| Endocannabinoids suppress excitatory synaptic transmission to dorsal raphe serotonin neurons through the activation of presynaptic CB1 receptors. | 2009 Oct |
Patents
Sample Use Guides
ChIP assays were performed to evaluate whether R(+)WIN 55,212-2 could affect the binding of the NF-kB subunit, p65, to the ICAM-1 and IL-8 promoters. 1321N1 astrocytoma were pre-treated with or without R(+)WIN 55,212-2 (20 uM) for 1 h prior to stimulation for a further 1 h in the absence or presence of IL-1 (10 ng/ml). p65 was absent at the promoters in unstimulated 1321N1 cells, but after 1-h stimulation with IL-1, p65 was detected at both promoters.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 17 22:43:19 UTC 2022
by
admin
on
Sat Dec 17 22:43:19 UTC 2022
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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
Created by
admin on Sat Dec 17 22:43:19 UTC 2022 , Edited by admin on Sat Dec 17 22:43:19 UTC 2022
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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 Sat Dec 17 22:43:19 UTC 2022 , Edited by admin on Sat Dec 17 22:43:19 UTC 2022
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PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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TARGET -> AGONIST |
Mouse AtT-20 neuroblastoma cells stably transfected with human CB2
EC50
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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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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
