SIN-1 Chloride

SIN-1 Chloride

Cayman Chemical Item Number 82220

Linsidomine; 3-Morpholino-sydnonimine (CAS 16142-27-1)

SIN-1 Chloride (CAS 16142-27-1)

Description

As the active metabolite of molsidomine, SIN-1 chloride is a potent vasorelaxant and inhibitor of platelet aggregation. It produces both NO and superoxide and can therefore be used to generate peroxynitrite under physiological conditions.^1,2,3

1 Rosenkranz, B., Winkelmann, B.R., and Parnham, M.J. Clinical pharmacokinetics of molsidomine. Clin Pharmacokinet 30 372-384 (1996).

2 Lomonosova, E.E., Kirsch, M., Rauen, U., et al. The critical role of hepes in SIN-1 cytotoxicity, peroxynitrite versus hydrogen peroxide. Free Radic Biol Med 24 522-528 (1998).

3 Nishikawa, M., Kanamori, M., and Hidaka, H. Inhibition of platelet aggregation and stimulation of guanylate cyclase by an antianginal agent molsidomine and its metabolites. J Pharmacol Exp Ther 220 183-190 (1982).

Synonyms

Linsidomine
3-Morpholino-sydnonimine

Formal Name

5-amino-3-(4-morpholinyl)-1,2,3-oxadiazolium chloride

CAS Number

16142-27-1

Molecular Formula

C₆H₁₁N₄O₂ · Cl

Formula Weight

206.6

Formulation

A crystalline solid

Purity

>99%

λ_max

253, 296 nm

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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NC1=C[N+](N2CCOCC2)=NO1.[Cl-]

Background Reading

Henry, P.J., Horowitz, J.D., and Louis, W.J. Nitroglycerin-induced tolerance affects multiple sites in the organic nitrate bioconversion cascade. J Pharmacol Exp Ther 248 762-768 (1989).

Rosenkranz, B., Winkelmann, B.R., and Parnham, M.J. Clinical pharmacokinetics of molsidomine. Clin Pharmacokinet 30 372-384 (1996).

Sanduja, S.K., Tsai, A., Matijevic-Aleksic, N., et al. Kinetics of prostacyclin synthesis in PGHS-1-overexpressed endothelial cells. Am J Physiol 267 C1459-C1466 (1994).

Lipton, S.A., Choi, Y., Pan, Z., et al. A redox-based mechanism for the neuroprotective and neurodestructive effects of nitric oxide and related nitroso-compounds. Nature 364 626-632 (1993).

Nishikawa, M., Kanamori, M., and Hidaka, H. Inhibition of platelet aggregation and stimulation of guanylate cyclase by an antianginal agent molsidomine and its metabolites. J Pharmacol Exp Ther 220 183-190 (1982).

Lomonosova, E.E., Kirsch, M., Rauen, U., et al. The critical role of hepes in SIN-1 cytotoxicity, peroxynitrite versus hydrogen peroxide. Free Radic Biol Med 24 522-528 (1998).

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