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2-Methyl-2-thiopseudourea sulfate
  • 2-Methyl-2-thiopseudourea sulfate2-Methyl-2-thiopseudourea sulfate

2-Methyl-2-thiopseudourea sulfate

Model: 867-44-7
2-Methyl-2-thiopseudourea Sulfate (S-Methylisothiourea sulfate, CAS 867-44-7) is a sulfur-containing guanidino compound and a potent inhibitor of nitric oxide synthase (NOS). Structurally, 2-Methyl-2-thiopseudourea Sulfate consists of a methyl isothiourea cation (C₂H₆N₂S⁺) associated with a sulfate anion, existing as the hemisulfate salt with a 2:1 stoichiometry (two methylisothiourea cations per sulfate).

2-Methyl-2-thiopseudourea Sulfate is a potent inhibitor of nitric oxide synthase (NOS) used in biomedical research to study the role of nitric oxide in various physiological and pathological processes . The compound is structurally similar to L-arginine, enabling 2-Methyl-2-thiopseudourea Sulfate to act as a competitive inhibitor of NOS with selectivity for the inducible isoform (iNOS). 2-Methyl-2-thiopseudourea Sulfate is also used as an intermediate in the synthesis of 4-hydroxydebrisoquine and related pharmaceutical compounds . As a guanidinating reagent, 2-Methyl-2-thiopseudourea Sulfate serves as an alternative to O-methylisourea for the conversion of lysine to homoarginine in peptides, though with lower efficiency .

 

Product Parameters

Parameter

Specification

Product Name

2-Methyl-2-thiopseudourea Sulfate

CAS Number

867-44-7

Molecular Formula

C₂H₈N₂O₄S₂

Molecular Weight

188.23 g/mol

Appearance

White crystalline powder 

Melting Point

240-241 °C (dec.)(lit.) 

Density

1.28 g/cm³ at 20 °C 

pH

5.5 (260 g/L, H₂O, 20 °C) 

pKa

pK1: 9.83 (+1) at 25 °C 

Storage Condition

Inert atmosphere, room temperature 

 

Application

2-Methyl-2-thiopseudourea sulfate is an intermediate for the preparation of guanidines, which can be used to prepare fungicides such as dimethirimol, ethirimol, insecticides such as pirimioxyphos, pirimicarb, etc.

 

Synthetic Route

The preparation method is as follows: add thiourea into the reactor, add a small amount of water, partially dissolve the thiourea under stirring, stir for 10 min under cooling in a cold water bath, then add redistilled dimethyl sulfate, quickly install two spherical condensers to prevent bumping, remove the cold water bath, the reaction proceeds spontaneously with exotherm, and sudden bumping occurs after 5 min. At this time, most of the solid has dissolved. After the reflux weakens and reaches equilibrium, heat and reflux for another 1 h, let it stand overnight, the reactant solidifies. Add 95% ethanol and stir for a moment, cool in ice water for 0.5 h, filter, and wash with 25% ethanol to obtain the finished product.

 

Product Advantages

 Potent Nitric Oxide Synthase Inhibitor

2-Methyl-2-thiopseudourea Sulfate is a potent inhibitor of nitric oxide synthase (NOS), with selectivity for the inducible isoform (iNOS) over endothelial (eNOS) and neuronal (nNOS) isoforms. This selectivity makes it a valuable tool for studying the role of nitric oxide in inflammation and sepsis .

 

 Structural Analog of L‑Arginine

2-Methyl-2-thiopseudourea Sulfate contains a guanidino group structurally similar to that of L-arginine, the natural substrate of NOS. This structural mimicry enables competitive inhibition of the enzyme .

 

 Dual Use: NOS Inhibitor and Guanidination Reagent

2-Methyl-2-thiopseudourea Sulfate serves both as a pharmacological tool (NOS inhibitor) and as a chemical reagent (guanidination agent for peptide modification) .

 

 Well-Characterized Reference Standard

2-Methyl-2-thiopseudourea Sulfate is a well-characterized compound with established physicochemical properties, making it suitable for use as a reference standard in pharmaceutical analysis.

 

Contact Us

From nitric oxide research to pharmaceutical synthesis, Cosperpharm provides the high-quality NOS inhibitors and guanidination reagents you need. Reach out to discuss your 2-Methyl-2-thiopseudourea Sulfate requirements today.

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