Introduction：Basic information about CAS 209589-59-3|S-methyl-L-Thiocitrulline hydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | S-methyl-L-Thiocitrulline hydrochloride |
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| CAS Number | 209589-59-3 | Molecular Weight | 278.20 |
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| Density | 1.35g/cm3 | Boiling Point | 405ºC at 760mmHg |
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| Molecular Formula | C7H17Cl2N3O2S | Melting Point | / |
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| MSDS | / | Flash Point | 198.7ºC |
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Names
| Name | S-Methyl-L-thiocitrulline dihydrochloride |
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| Synonym | More Synonyms |
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S-methyl-L-Thiocitrulline hydrochloride BiologicalActivity
| Description | S-MTC (S-Methyl-L-thiocitrulline) dihydrochloride is a selective type I nitric oxide synthase (NOS) inhibitor. |
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| Related Catalog | Signaling Pathways >>Immunology/Inflammation >>NO SynthaseResearch Areas >>Neurological Disease |
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| Target | NOS[1] |
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| 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]. |
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| 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]. |
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| 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. |
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Chemical & Physical Properties
| Density | 1.35g/cm3 |
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| Boiling Point | 405ºC at 760mmHg |
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| Molecular Formula | C7H17Cl2N3O2S |
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| Molecular Weight | 278.20 |
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| Flash Point | 198.7ºC |
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| Exact Mass | 277.041840 |
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| PSA | 127.00000 |
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| LogP | 2.86080 |
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| InChIKey | JNZHDSKJUXGYRG-XRIGFGBMSA-N |
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| SMILES | CSC(N)=NCCCC(N)C(=O)O.Cl.Cl |
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Safety Information
| Safety Phrases | S24/25 |
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| HS Code | 2930909090 |
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Customs
| HS Code | 2930909090 |
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| Summary | 2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0% |
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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 |
