s-methyl-l-thiocitrulline
Modify Date: 2024-01-09 17:23:39
s-methyl-l-thiocitrulline structure
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Common Name | s-methyl-l-thiocitrulline | ||
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| CAS Number | 156719-41-4 | Molecular Weight | 205.28 | |
| Density | 1.35 g/cm3 | Boiling Point | 405ºC at 760 mmHg | |
| Molecular Formula | C7H15N3O2S | Melting Point | 60ºC | |
| MSDS | N/A | Flash Point | 198.7ºC | |
Use of s-methyl-l-thiocitrullineS-MTC is a selective type I nitric oxide synthase (NOS) inhibitor. |
| Name | s-methyl-l-thiocitrulline |
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| Synonym | More Synonyms |
| Description | S-MTC is a selective type I nitric oxide synthase (NOS) inhibitor. |
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| Related Catalog | |
| Target |
NOS[1] |
| In Vitro | S-MTC (10 or 100 μM) reduces cellular NO release in the absence of Aβ1-42. At 100 μM, S-MTC decreases cell viability. S-MTC (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 (100 μM) treatments are significantly lower than Aβ1-42 alone (33.5±2.0 and 34.5±1.6 μM, respectively). S-MTC (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 (100 μM) concentration decreases both MTT (87±1% of control) and NR (80±1% of control, respectively) levels. The co-administration of S-MTC (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 (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]. |
| Cell Assay | Mixed cortical glial and neuronal cultured cells are prepared from E15 to E18 embryos obtained from Spargue-Dawley rats. On day 7 after plating, the culture medium is removed and replaced with freshly prepared culture medium in the presence of either Aβ1-42 (1, 5, 10, or 20 μM), Aβ42-1, or peroxynitrite (100 or 200 μM) with or without either NG-nitro-L-arginine (L-NOARG,10 or 100 μM), S-MTC (10 or 100 μM), N-iminoethyl-L-lysine (10 or 100 μM), N-(3-(aminomethyl)benzyl)acetamidine (1400W,1 or 5 μM), 2-(4-carboxyphenyl)-4, 4, 5, 5-tetramethylimidazoline-1-oxyl-3-oxide (carboxy-PTIO,10 or 100 μM), or 6-hydorxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (10 or 100 μM) alone or in combination. The cultured cells are then incubated for 20 h. For the time-course studies, the cultured cells are pre-treated with the described culture medium containing Aβ1-42 (10 μM). Either L-NIL (100 μM), L-NOARG (100 μM), 1400W (5 μM), S-MTC (100 μM), carboxy-PTIO (100 μM) or Trolox (100 μM) are administered at 1, 4, and 8 h later. Assessments are carried out 20 h after Aβ1-42 administration. The viability of cultured cells is evaluated by using MTT and neutral red colorimetric assays. MTT reduction and NR uptake are quantified at 570 and 540 nm, respectively, by using a micro-plate reader[1]. |
| Animal Admin | mice[2] Male NIH Swiss mice, weighing 18-22 g, are used. S-MTC (1.0 μg/mouse) is administered i.c.v. (15-min pretreatment time). In one set of experiments (#1, #2, and #3), opioid antagonists and NOS-inhibitors are administered 15–30 min prior to the 60-min HBO2 treatment (180 min prior to antinociceptive testing). In another experiment (#4), opioid antagonist and NOS-inhibitor pretreatment is administered 60 min following cessation of the 60-min HBO2 treatment (15–30 min prior to antinociceptive testing). For i.p. or s.c. pretreatments, the volume of injection is 0.1 mL/10 g body weight with control animals receiving an i.p. or s.c. injection of vehicle (sterile saline) only. For i.c.v. pretreatments, the volume of microinjection is 5.0 μL per mouse with control animals receiving an i.c.v. microinjection of vehicle (sterile saline) only. Rats[3] Male, Sprague-Dawley rats (350-450 g) are used. On the day after catheterisation (day 1), animals (n=7) receive bolus i.v. injections (0.1 mL) of either saline (vehicle), and 0.3 and 3 mg/kg S-MTC (n=4), or 0.1, 1 and 10 mg/kg S-MTC (n=3). On day 3, the dose regimen is switched to ensure that each animal has received all the doses of S-MTC. On each day, drugs are given in ascending dose-order, and at least 60 min is allowed between doses. The intervening day (day 2) is allowed for wash-out of any drug effects. |
| References |
| Density | 1.35 g/cm3 |
|---|---|
| Boiling Point | 405ºC at 760 mmHg |
| Melting Point | 60ºC |
| Molecular Formula | C7H15N3O2S |
| Molecular Weight | 205.28 |
| Flash Point | 198.7ºC |
| PSA | 161.80000 |
| LogP | 1.34770 |
| Index of Refraction | 1.572 |
| Storage condition | 2-8℃ |
Synonym:None Known Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
Risk Phrases: None Listed. Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated. Potential Health Effects Eye: May cause eye irritation. Skin: May cause skin irritation. May be harmful if absorbed through the skin. Ingestion: May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed. Inhalation: May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled. Chronic: No information found. Section 4 - FIRST AID MEASURES Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid. Skin: In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse. Ingestion: If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid. Inhalation: If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Notes to Physician: Treat symptomatically and supportively. Section 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Storage: Store in a tightly closed container. Keep refrigerated. (Store below 4C/39F.) Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 156719-41-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure. Respirators: Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Powder Color: white - off-white Odor: odorless pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 60 deg C Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: Soluble. Specific Gravity/Density: Molecular Formula: C6H13N3O2S.2HCl Molecular Weight: 264.3 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable. Conditions to Avoid: Dust generation, moisture, excess heat. Incompatibilities with Other Materials: Strong oxidizing agents. Hazardous Decomposition Products: Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide. Hazardous Polymerization: Will not occur. Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 156719-41-4 unlisted. LD50/LC50: Not available. Carcinogenicity: L-Thiocitrulline dihydrochloride - Not listed by ACGIH, IARC, or NTP. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material. Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: Not available. Risk Phrases: Safety Phrases: S 24/25 Avoid contact with skin and eyes. WGK (Water Danger/Protection) CAS# 156719-41-4: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 156719-41-4 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 156719-41-4 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A |
| s-methylthiocitrulline |
| S-Me-TC,SMTC |
| L-Thiocitrulline2HCl |
| S-MTC |