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156719-41-4

156719-41-4 Structure

156719-41-4 Structure
IdentificationBack 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 PropertiesBack 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)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack 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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