S-METHYL-L-THIOCITRULLINE
S-METHYL-L-THIOCITRULLINE Basic information
- Product Name:
- S-METHYL-L-THIOCITRULLINE
- Synonyms:
-
- S-METHYL-L-THIOCITRULLINE
- S-METHYL-L-THIOCITRULLINE ACETATE
- H-THIOCIT(S-ME)-OH ACOH
- s-methylthiocitrulline
- L-Thiocitrulline2HCl
- (2S)-2-amino-5-[[amino(methylsulfanyl)methylidene]amino]pentanoic acid
- (2S)-2-amino-5-[[amino-(methylthio)methylene]amino]valeric acid
- (2S)-2-azanyl-5-[[azanyl(methylsulfanyl)methylidene]amino]pentanoic acid
- CAS:
- 156719-41-4
- MF:
- C7H15N3O2S
- MW:
- 205.28
- Mol File:
- 156719-41-4.mol
S-METHYL-L-THIOCITRULLINE Chemical Properties
- 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)
S-METHYL-L-THIOCITRULLINE Usage And Synthesis
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].
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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