Identification | Back Directory | [Name]
S-METHYL-L-THIOCITRULLINE | [CAS]
156719-41-4 | [Synonyms]
S-MTC S-Me-TC, SMTC L-Thiocitrulline2HCl s-methylthiocitrulline H-THIOCIT(S-ME)-OH ACOH S-METHYL-L-THIOCITRULLINE S-METHYL-L-THIOCITRULLINE ACETATE L-Ornithine, N5-[imino(methylthio)methyl]- (2S)-2-amino-5-[[amino-(methylthio)methylene]amino]valeric acid (S,E)-2-aMino-5-((aMino(Methylthio)Methylene)aMino)pentanoic acid (2S)-2-amino-5-[[amino(methylsulfanyl)methylidene]amino]pentanoic acid (2S)-2-azanyl-5-[[azanyl(methylsulfanyl)methylidene]amino]pentanoic acid | [Molecular Formula]
C7H15N3O2S | [MDL Number]
MFCD00798234 | [MOL File]
156719-41-4.mol | [Molecular Weight]
205.28 |
Chemical Properties | Back Directory | [Boiling point ]
369.4±52.0 °C(Predicted) | [density ]
1.35±0.1 g/cm3(Predicted) | [storage temp. ]
Store at 0°C | [solubility ]
Soluble in DMSO | [pka]
2.48±0.24(Predicted) |
Hazard Information | Back Directory | [Uses]
S-MTC is a selective type I nitric oxide synthase (NOS) inhibitor. | [Definition]
ChEBI: An L-arginine derivative in which the guanidino NH2 group of L-arginine is replaced by a methylsufanyl group. | [in vivo]
S-MTC (S-methyl-L-thiocitrulline) is a selective neuronal NOS-inhibitor. Following pretreatment with S-MTC (i.c.v.), the HBO2-induced antinociception is significantly antagonized. In Experiment #2, different groups of mice are pretreated with naltrexone hydrochloride (NTX) (3.0 mg/kg, i.p.), L-NAME (1.0 μg/mouse, i.c.v.), S-MTC (1.0 μg/mouse, i.c.v.) or N5-(1-iminoethyl)-L-ornithine (L-NIO) (3.0 mg/kg, s.c.) 15-30 min prior to HBO2 treatment. The antinociceptive effect assessed 90 min after HBO2 treatment is completely abolished by NTX and L-NAME, antagonized by two-thirds by S-MTC and largely unaffected by L-NIO (F=25.57, p<0.0001)[2]. At a dose of 0.3 mg/kg, S-MTC (SMTC) causes a rise in mean blood pressure (BP). At doses of 1.0, 3.0 and 10 mg/kg, S-MTC causes falls in heart rate, rises in BP and vasoconstriction in all three vascular beds[3]. | [storage]
Store at -20°C | [References]
[1] Law A, et al. Neuroprotective and neurorescuing effects of isoform-specific nitric oxide synthase inhibitors, nitric oxide scavenger, and antioxidant against beta-amyloid toxicity. Br J Pharmacol. 2001 Aug;133(7):1114-24. DOI:10.1038/sj.bjp.0704179 [2] Zelinski LM, et al. A prolonged nitric oxide-dependent, opioid-mediated antinociceptive effect of hyperbaric oxygenin mice. J Pain. 2009 Feb;10(2):167-72. DOI:10.1016/j.jpain.2008.08.003 [3] Wakefield ID, et al. Comparative regional haemodynamic effects of the nitric oxide synthase inhibitors, S-methyl-L-thiocitrulline and L-NAME, in conscious rats. Br J Pharmacol. 2003 Jul;139(6):1235-43. DOI:10.1038/sj.bjp.0705351 |
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