S-methyl-L-Thiocitrulline hydrochloride

Modify Date: 2024-01-20 10:38:28

S-methyl-L-Thiocitrulline hydrochloride Structure
S-methyl-L-Thiocitrulline hydrochloride structure
Common Name S-methyl-L-Thiocitrulline hydrochloride
CAS Number 209589-59-3 Molecular Weight 278.20
Density 1.35g/cm3 Boiling Point 405ºC at 760mmHg
Molecular Formula C7H17Cl2N3O2S Melting Point N/A
MSDS N/A Flash Point 198.7ºC

 Use of S-methyl-L-Thiocitrulline hydrochloride


S-MTC (S-Methyl-L-thiocitrulline) dihydrochloride is a selective type I nitric oxide synthase (NOS) inhibitor.

 Names

Name S-Methyl-L-thiocitrulline dihydrochloride
Synonym More Synonyms

 S-methyl-L-Thiocitrulline hydrochloride Biological Activity

Description S-MTC (S-Methyl-L-thiocitrulline) dihydrochloride is a selective type I nitric oxide synthase (NOS) inhibitor.
Related Catalog
Target

NOS[1]

In Vitro S-MTC dihydrochloride (10 or 100?μM) reduces cellular NO release in the absence of Aβ1-42. At 100?μM, S-MTC dihydrochloride decreases cell viability. S-MTC dihydrochloride (100?μM) significantly lowers nitrite production (11.2±1.1?μM) when compared to control (no NOS inhibitor exposure; 19.6±1.2?μM). Nitrite productions after Aβ1-42 and L-NOARG (100?μM) or Aβ1-42 and S-MTC dihydrochloride (100?μM) treatments are significantly lower than Aβ1-42 alone (33.5±2.0 and 34.5±1.6?μM, respectively). S-MTC dihydrochloride (100?μM) is able to significantly reduce nitrite production (25.2±1.1?μM) as compared to Aβ1-42 treatment alone (38.3±2.7?μM), when administered after Aβ1-42 at the 1?h time point. S-MTC dihydrochloride (100?μM) concentration decreases both MTT (87±1% of control) and NR (80±1% of control, respectively) levels. The co-administration of S-MTC dihydrochloride (100?μM) and Aβ1-42 significantly reverses the effects of Aβ1-42 alone (72±2% vs 61±2% of control)[1].
In Vivo S-MTC dihydrochloride (S-methyl-L-thiocitrulline) is a selective neuronal NOS-inhibitor. Following pretreatment with S-MTC dihydrochloride (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 dihydrochloride (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 dihydrochloride and largely unaffected by L-NIO (F=25.57, p<0.0001)[2]. At a dose of 0.3 mg/kg, S-MTC dihydrochloride (SMTC) causes a rise in mean blood pressure (BP). At doses of 1.0, 3.0 and 10 mg/kg, S-MTC dihydrochloride 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.  

[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.  

[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.  

 Chemical & Physical Properties

Density 1.35g/cm3
Boiling Point 405ºC at 760mmHg
Molecular Formula C7H17Cl2N3O2S
Molecular Weight 278.20
Flash Point 198.7ºC
Exact Mass 277.041840
PSA 127.00000
LogP 2.86080

 Safety Information

Safety Phrases S24/25
HS Code 2930909090

 Customs

HS Code 2930909090
Summary 2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

 Synonyms

S-Methyl (2S)-2-amino-5-(carbamoylamino)pentanethioate dihydrochloride
L-Ornithine, N-[amino(methylthio)methylene]-, (Z)-, hydrochloride (1:2)
Pentanethioic acid, 2-amino-5-[(aminocarbonyl)amino]-, S-methyl ester, (2S)-, hydrochloride (1:2)
(Z)-N-[Amino(methylsulfanyl)methylene]-L-ornithine dihydrochloride
S-MTC dihydrochloride
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