S-Methylisothiourea sulfate

Names

[ CAS No. ]:
867-44-7

[ Name ]:
S-Methylisothiourea sulfate

[Synonym ]:
S-Methyl-isothiouronium Hemisulfate
S-METHYLTHIOPSEUDOUREA SULPHATE
2-Methyl-2-thiopseudourea sulfate
2-Methyl-2-thiopseudourea hemisulfate
S-METHYLISOTHIOHARNSTOFF HEMISULFAT
S-methylisothiourea sulfuric acid salt 1:1
S-EIT hemihydrate
2-methyl-2-thiopseudouronium sulfate
S-METHYLISOTHIOURONIUM SULPHATE
2-Methyl-2-thiopseudoureasulfate
S-METHYL-ISO-THIOUREA SULFATE
S-Methylisothiourea Hemisulfate Salt
S-METHYLISOTHIOURONIUM SULPHATE/S-METHYLISOTHIOUREA SULPHATE/2-METHYL-2-THIOPSEUDOUREA SULPHATE
2-METHYL-2-THIOPSEUDOUREA SULFATE (S-METHYLISOTHIOUREA SULFATE)
MFCD00129752
methyl imidothiocarbamate
S-METHYL ISOTHIOUREA SULFATE
Carbamimidothioic acid, methyl ester, sulfate (2:1)
S-methyl-2-thiopseudourea hydrogen sulfate
S-METHYLTHIOURONIUM SULFATE
S-methylisothiourea hydrogensulfate
S-Methyl-ITU
S-MethyliSothourea Sulfate
methyl imidothiocarbamate sulfate
2-Methyl-2-thiopseud
EINECS 212-759-7
S-methyl isothiourea sultate
2-METHYL-2-THIOPSEUDO UREA 14C SULFATE
S-METHYL-ISO-THIOUREA
S-methyl Isothiourea (hemisulfate)
S-METHYLISOTHIOURONIUM SULFATE
5-METHYLISOTHIOUREA HEMISULFATE
Carbamimidothioic acid, methyl ester, sulfate (1:1)
(S)-METHYLISOTHIOUREA SULFATE
METHYLTHIOURONIUMSULPHATE
Methyl carbamimidothioate sulfate (1:1)
S-METHYLTHIOUREA
S-METHYL-2-ISOTHIOUREA HEMISULPHATE
S-methylisothiouronium hydrogensulfate
methyl carbamimidothioate
S-METHYLISOTHIOUREASULFATE
S-METHYLTHIOURONIUM SULFATE FOR SYNTHESIS
S-Methylisothiourea hemisulfate
S-METHYLISOTHIOUREA HEMISULFATE SALT _X000D_
S-Methylisothiourea sulfate
IMINO(METHYLSULFANYL)METHYLAMINE
Amino(methylsulfanyl)methaniminium hydrogen sulfate (1:1:1)
S-Methyl-ITU . sulfate
S-METHYLTHIOURONIUMSULFATE(2:1)
METHYLTHIURONIUMSULPHATE
2-METHYL-ISOTHIOUREA

Biological Activity

[Description]:

S-Methylisothiourea sulfate is a potent, selective and competitive inhibitor of inducible nitric oxide synthase (iNOS). S-Methylisothiourea sulfate exerts beneficial effects in rodent models of septic shock[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Immunology/Inflammation >> NO Synthase

[Target]

iNOS[1]

[In Vitro]

S-Methylisothiourea sulfate is a competitive inhibitor of iNOS activity at the L-arginine site[1]. S-Methylisothiourea sulfate prevents the NO-mediated cytotoxic effect of LPS in cultured macrophages[1]. S-Methylisothiourea sulfate (100 nM-100 μM) exhibits inhibitory effects on LPS (ug/mL)-induced nitrite production in J774.2 macrophages and rat aortic vascular smooth muscle cells[1]. S-Methylisothiourea sulfate(up to 1 mM) does not inhibit the activity of xanthine oxidase, diaphorase, lactate dehydrogenase, monoamine oxidase, catalase, cytochrome P450, or superoxide dismutase[1].

[In Vivo]

S-Methylisothiourea sulfate (0.01-3 mg/kg; i.v.) dose-dependently reverses the hypotension and the vascular hyporeactivity to vasoconstrictor agents caused by endotoxin LPS in anesthetized rats[1]. S-Methylisothiourea sulfate (5 mg/kg; i.p.; given 2 hr after LPS; 10 mg/kg, i.p.) attenuates the rises in plasma alanine and aspartate aminotransferases, bilirubin, and creatinine and also prevents hypocalcaemia when measured 6 hr after administration of LPS[1]. S-Methylisothiourea sulfate (1 mg/kg; i.p.) improves 24-hr survival of mice treated with a high dose of LPS (60 mg/kg; i.p.)[1]. Animal Model: Male Wistar rats (260-320 g)[1] Dosage: 0.01 mg/kg, 0.1 mg/kg, 1 mg/kg, 3 mg/kg Administration: Intravenous injection Result: Caused a prompt restoration of the blood pressure to pre-LPS levels at 3 mg/kg dose in LPS (10 mg/kg, i.v.)-treated rats; Inhibits iNOS activity measured in homogenates of lung.

[References]

[1]. C Szabó, et al. Beneficial effects and improved survival in rodent models of septic shock with S-methylisothiourea sulfate, a potent and selective inhibitor of inducible nitric oxide synthase. Proc Natl Acad Sci U S A. 1994 Dec 20; 91(26): 12472–12476.

Chemical & Physical Properties

[ Density]:
1.28

[ Boiling Point ]:
138.8ºC at 760 mmHg

[ Melting Point ]:
240-241 °C (dec.)(lit.)

[ Molecular Formula ]:
C₂H₈N₂O₄S₂

[ Molecular Weight ]:
188.226

[ Flash Point ]:
37.7ºC

[ Exact Mass ]:
187.992554

[ PSA ]:
158.15000

[ LogP ]:
1.47090

[ Storage condition ]:
Store at RT

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
260 g/L (20 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UM9200000

CAS REGISTRY NUMBER :: 867-44-7

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C4-H12-N4-S2.H2-O4-S

MOLECULAR WEIGHT :: 278.40

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: AD438-895

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 180 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#05644

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 663 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 14,700,1959

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UM9200000

[ HS Code ]:
2930909090

Precursor & DownStream

Precursor

DownStream

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%

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