WIN 55212-2 mesylate
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 526795

CAS#: 131543-23-2

Description: WIN 55212-2 is a CB1 agonist (cannabinoid receptor agonist). WIN 55212-2 impairs contextual fear conditioning through the activation of CB1 cannabinoid receptors. Win 55212-2 attenuates leukocyte/endothelial interactions in an experimental autoimmune encephalomyelitis model. WIN 55212-2 inhibits neurogenic inflammations in airway tissues.


Price and Availability

Size
Price

100mg
USD 450
1g
USD 2450
Size
Price

200mg
USD 750
2g
USD 3850
Size
Price

500mg
USD 1550

WIN 55212-2 mesylate, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526795
Name: WIN 55212-2 mesylate
CAS#: 131543-23-2
Chemical Formula: C28H30N2O6S
Exact Mass:
Molecular Weight: 522.616
Elemental Analysis: C, 64.35; H, 5.79; N, 5.36; O, 18.37; S, 6.13


Related CAS #: 131543-23-2 (mesylate)   131543-22-1 (free base)  

Synonym: WIN 55212-2; WIN55212-2; WIN-55212-2; WIN 552122; WIN552122; WIN-552122; WIN 55,212-2 mesylate

IUPAC/Chemical Name: [(3R)-2,3-dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenyl-methanone, monomethanesulfonate

InChi Key: FSGCSTPOPBJYSX-VEIFNGETSA-N

InChi Code: InChI=1S/C27H26N2O3.CH4O3S/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;1-5(2,3)4/h2-11,20H,12-17H2,1H3;1H3,(H,2,3,4)/t20-;/m1./s1

SMILES Code: O=C(C1=C(C)N2[C@H](CN3CCOCC3)COC4=CC=CC1=C24)C5=C6C=CC=CC6=CC=C5.CS(=O)(O)=O


Technical Data

Appearance:
White to off-white crystalline powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Related CAS#
131543-23-2 (WIN 55212-2 mesylate);
131543-22-1 (WIN 55212-2 free base).


References

1: Rodríguez-Arias M, Roger-Sánchez C, Vilanova I, Revert N, Manzanedo C, Miñarro J, Aguilar MA. Effects of Cannabinoid Exposure during Adolescence on the Conditioned Rewarding Effects of WIN 55212-2 and Cocaine in Mice: Influence of the Novelty-Seeking Trait. Neural Plast. 2016;2016:6481862. doi: 10.1155/2016/6481862. Epub 2015 Dec 31. PubMed PMID: 26881125; PubMed Central PMCID: PMC4736006.

2: Shabani M, Mahnam A, Sheibani V, Janahmadi M. Alterations in the intrinsic burst activity of Purkinje neurons in offspring maternally exposed to the CB1 cannabinoid agonist WIN 55212-2. J Membr Biol. 2014 Jan;247(1):63-72. doi: 10.1007/s00232-013-9612-1. Epub 2013 Nov 12. PubMed PMID: 24218023.

3: Pinar-Sueiro S, Zorrilla Hurtado JÁ, Veiga-Crespo P, Sharma SC, Vecino E. Neuroprotective effects of topical CB1 agonist WIN 55212-2 on retinal ganglion cells after acute rise in intraocular pressure induced ischemia in rat. Exp Eye Res. 2013 May;110:55-8. doi: 10.1016/j.exer.2013.02.009. Epub 2013 Feb 20. PubMed PMID: 23454099.

4: Shabani M, Divsalar K, Janahmadi M. Destructive Effects of Prenatal WIN 55212-2 Exposure on Central Nervous System of Neonatal Rats. Addict Health. 2012 Winter-Spring;4(1-2):9-19. PubMed PMID: 24494131; PubMed Central PMCID: PMC3905554.

5: Alonso-Alconada D, Alvarez A, Alvarez FJ, Martínez-Orgado JA, Hilario E. The cannabinoid WIN 55212-2 mitigates apoptosis and mitochondrial dysfunction after hypoxia ischemia. Neurochem Res. 2012 Jan;37(1):161-70. doi: 10.1007/s11064-011-0594-z. Epub 2011 Sep 11. PubMed PMID: 21909954.

6: Acheson SK, Moore NL, Kuhn CM, Wilson WA, Swartzwelder HS. The synthetic cannabinoid WIN 55212-2 differentially modulates thigmotaxis but not spatial learning in adolescent and adult animals. Neurosci Lett. 2011 Jan 10;487(3):411-4. doi: 10.1016/j.neulet.2010.10.067. Epub 2010 Nov 3. PubMed PMID: 21055447; PubMed Central PMCID: PMC3035942.

7: Shabani M, Hosseinmardi N, Haghani M, Shaibani V, Janahmadi M. Maternal exposure to the CB1 cannabinoid agonist WIN 55212-2 produces robust changes in motor function and intrinsic electrophysiological properties of cerebellar Purkinje neurons in rat offspring. Neuroscience. 2011 Jan 13;172:139-52. doi: 10.1016/j.neuroscience.2010.10.031. Epub 2010 Oct 20. PubMed PMID: 20969930.

8: Manzanedo C, Rodríguez-Arias M, Daza-Losada M, Maldonado C, Aguilar MA, Miñarro J. Effect of the CB1 cannabinoid agonist WIN 55212-2 on the acquisition and reinstatement of MDMA-induced conditioned place preference in mice. Behav Brain Funct. 2010 Mar 22;6:19. doi: 10.1186/1744-9081-6-19. PubMed PMID: 20307280; PubMed Central PMCID: PMC2858089.

9: Rodríguez-Arias M, Manzanedo C, Roger-Sánchez C, Do Couto BR, Aguilar MA, Miñarro J. Effect of adolescent exposure to WIN 55212-2 on the acquisition and reinstatement of MDMA-induced conditioned place preference. Prog Neuropsychopharmacol Biol Psychiatry. 2010 Feb 1;34(1):166-71. doi: 10.1016/j.pnpbp.2009.10.019. Epub 2009 Oct 30. PubMed PMID: 19883712.

10: Accorsi-Mendonça D, Almado CE, Dagostin AL, Machado BH, Leão RM. Inhibition of spontaneous neurotransmission in the nucleus of solitary tract of the rat by the cannabinoid agonist WIN 55212-2 is not via CB1 or CB2 receptors. Brain Res. 2008 Mar 20;1200:1-9. doi: 10.1016/j.brainres.2008.01.011. Epub 2008 Jan 16. PubMed PMID: 18308297.

11: Benagiano V, Lorusso L, Flace P, Girolamo F, Rizzi A, Sabatini R, Auteri P, Bosco L, Cagiano R, Ambrosi G. Effects of prenatal exposure to the CB-1 receptor agonist WIN 55212-2 or CO on the GABAergic neuronal systems of rat cerebellar cortex. Neuroscience. 2007 Nov 9;149(3):592-601. Epub 2007 Aug 19. PubMed PMID: 17916407.

12: Rawls SM, Gomez T, Raffa RB. An NMDA antagonist (LY 235959) attenuates abstinence-induced withdrawal of planarians following acute exposure to a cannabinoid agonist (WIN 55212-2). Pharmacol Biochem Behav. 2007 Mar;86(3):499-504. Epub 2007 Jan 20. PubMed PMID: 17306870.

13: Marchalant Y, Rosi S, Wenk GL. Anti-inflammatory property of the cannabinoid agonist WIN-55212-2 in a rodent model of chronic brain inflammation. Neuroscience. 2007 Feb 23;144(4):1516-22. Epub 2006 Dec 18. PubMed PMID: 17178196; PubMed Central PMCID: PMC1852513.

14: Rawls SM, Tallarida RJ, Zisk J. Agmatine and a cannabinoid agonist, WIN 55212-2, interact to produce a hypothermic synergy. Eur J Pharmacol. 2006 Dec 28;553(1-3):89-98. Epub 2006 Aug 26. PubMed PMID: 17109846.

15: Rawls SM, Rodriguez T, Baron DA, Raffa RB. A nitric oxide synthase inhibitor (L-NAME) attenuates abstinence-induced withdrawal from both cocaine and a cannabinoid agonist (WIN 55212-2) in Planaria. Brain Res. 2006 Jul 12;1099(1):82-7. Epub 2006 Jun 19. PubMed PMID: 16782070.

16: Struik ML, Yazulla S, Kamermans M. Cannabinoid agonist WIN 55212-2 speeds up the cone response to light offset in goldfish retina. Vis Neurosci. 2006 Mar-Apr;23(2):285-93. PubMed PMID: 16638179.

17: Pamplona FA, Takahashi RN. WIN 55212-2 impairs contextual fear conditioning through the activation of CB1 cannabinoid receptors. Neurosci Lett. 2006 Apr 10-17;397(1-2):88-92. Epub 2006 Jan 6. PubMed PMID: 16406322.

18: Yoshihara S, Morimoto H, Ohori M, Yamada Y, Abe T, Arisaka O. The cannabinoid receptor agonist WIN 55212-2 inhibits neurogenic inflammations in airway tissues. J Pharmacol Sci. 2005 May;98(1):77-82. Epub 2005 May 12. PubMed PMID: 15888960.

19: Ni X, Geller EB, Eppihimer MJ, Eisenstein TK, Adler MW, Tuma RF. Win 55212-2, a cannabinoid receptor agonist, attenuates leukocyte/endothelial interactions in an experimental autoimmune encephalomyelitis model. Mult Scler. 2004 Apr;10(2):158-64. PubMed PMID: 15124761.

20: Rawls SM, Tallarida RJ, Gray AM, Geller EB, Adler MW. L-NAME (N omega-nitro-L-arginine methyl ester), a nitric-oxide synthase inhibitor, and WIN 55212-2 [4,5-dihydro-2-methyl-4(4-morpholinylmethyl)-1-(1-naphthalenyl-carbonyl)-6H-pyrro lo[3,2,1ij]quinolin-6-one], a cannabinoid agonist, interact to evoke synergistic hypothermia. J Pharmacol Exp Ther. 2004 Feb;308(2):780-6. Epub 2003 Nov 10. PubMed PMID: 14610231.