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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
Structure of WIN-55212-2

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

HIDE SMILES / InChI

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.

Approval Year

Doses

Doses

DosePopulationAdverse events​
50 ug single, topical (total daily dose)
Highest studied dose
Dose: 50 ug
Route: topical
Route: single
Dose: 50 ug
Sources:
unhealthy, ADULT
n = 8
Health Status: unhealthy
Condition: glaucoma
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 8
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors.
1995 Sep
Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands.
1996 Sep
Assessment of the role of CB1 receptors in cannabinoid anticonvulsant effects.
2001 Sep 28
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
Desensitization of cannabinoid-mediated presynaptic inhibition of neurotransmission between rat hippocampal neurons in culture.
2002 Mar
The rodent amygdala contributes to the production of cannabinoid-induced antinociception.
2003
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
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
Patents

Sample Use Guides

25 or 50 ug
Route of Administration: Topical
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 Thu Jul 06 13:41:20 UTC 2023
Edited
by admin
on Thu Jul 06 13:41:20 UTC 2023
Record UNII
5H31GI9502
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
WIN-55212-2
Code English
METHANONE, (2,3-DIHYDRO-5-METHYL-3-(4-MORPHOLINYLMETHYL)PYRROLO(1,2,3-DE)-1,4-BENZOXAZIN-6-YL)-1-NAPHTHALENYL-, (+)-
Systematic Name English
(R)-(+)-WIN-55212-2
Code English
J442.901J
Code English
WIN 55212-2
Code English
METHANONE, ((3R)-2,3-DIHYDRO-5-METHYL-3-(4-MORPHOLINYLMETHYL)PYRROLO(1,2,3-DE)-1,4-BENZOXAZIN-6-YL)-1-NAPHTHALENYL-
Systematic Name English
(R)-WIN-55212
Code English
Classification Tree Code System Code
WIKIPEDIA Designer-drugs-WIN-55212-2
Created by admin on Thu Jul 06 13:41:21 UTC 2023 , Edited by admin on Thu Jul 06 13:41:21 UTC 2023
Code System Code Type Description
DRUG BANK
DB13950
Created by admin on Thu Jul 06 13:41:21 UTC 2023 , Edited by admin on Thu Jul 06 13:41:21 UTC 2023
PRIMARY
FDA UNII
5H31GI9502
Created by admin on Thu Jul 06 13:41:21 UTC 2023 , Edited by admin on Thu Jul 06 13:41:21 UTC 2023
PRIMARY
CAS
131543-22-1
Created by admin on Thu Jul 06 13:41:21 UTC 2023 , Edited by admin on Thu Jul 06 13:41:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID40894849
Created by admin on Thu Jul 06 13:41:21 UTC 2023 , Edited by admin on Thu Jul 06 13:41:21 UTC 2023
PRIMARY
PUBCHEM
5311501
Created by admin on Thu Jul 06 13:41:21 UTC 2023 , Edited by admin on Thu Jul 06 13:41:21 UTC 2023
PRIMARY
CAS
131513-18-3
Created by admin on Thu Jul 06 13:41:21 UTC 2023 , Edited by admin on Thu Jul 06 13:41:21 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
WIN 55,212-2
Created by admin on Thu Jul 06 13:41:21 UTC 2023 , Edited by admin on Thu Jul 06 13:41:21 UTC 2023
PRIMARY
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