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About This Item
Linear Formula:
CH5N3O · 1/2H2SO4
CAS Number:
Molecular Weight:
124.11
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
biological source
synthetic (organic)
Quality Level
Assay
≥98% (TLC)
form
powder
solubility
water: 25 mg/mL, clear, colorless
storage temp.
2-8°C
SMILES string
NC(=N)NO.NC(=N)NO.OS(O)(=O)=O
InChI
1S/2CH5N3O.H2O4S/c2*2-1(3)4-5;1-5(2,3)4/h2*5H,(H4,2,3,4);(H2,1,2,3,4)
InChI key
MTGDDPZRXSDPFH-UHFFFAOYSA-N
Biochem/physiol Actions
An early antitumor agent. Oxidation results in release of NO, and formation of other reactive oxygen species, including peroxynitrite and peroxyl radicals. Reacts with NO to form an adduct which is a potent and stable vasodilator.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Zembowicz, A., et al.
British Journal of Pharmacology, 107, 1007-1007 (1992)
Kamil Brożewicz et al.
European journal of medicinal chemistry, 55, 384-394 (2012-08-16)
Twenty four 1-[2-alkylthio-5-(azol-2 or 5-yl)-4-chlorobenzenesulfonyl]-3-hydroxyguanidines 6a-x have been synthesized in order to evaluate their biological activity. Compounds 6a, 6c, 6d, 6f, 6g, 6i-p, 6r-t, and 6v-x were tested for their in vitro anticancer activity at the US National Cancer Institute. The
Rémy Ricoux et al.
European journal of biochemistry, 270(1), 47-55 (2002-12-21)
Nitric oxide (NO) is a potent intra- and intercellular messenger involved in the control of vascular tone, neuronal signalling and host response to infection. In mammals, NO is synthesized by oxidation of l-arginine catalysed by hemeproteins called NO-synthases with intermediate
Tingwei Cai et al.
Bioorganic & medicinal chemistry letters, 12(11), 1507-1510 (2002-05-29)
The electrochemical properties of a series of N-substituted-N'-hydroxyguanidines were studied. Two oxidation potentials of each compound were obtained by cyclic voltammetry. The E(ox1) values were from 0.51 to 0.62V, while the E(ox2) values were from 1.14 to 1.81V in acetonitrile
Oxidation of N-hydroxyguanidines by cytochromes P450 and NO-synthases and formation of nitric oxide.
Daniel Mansuy et al.
Drug metabolism reviews, 34(3), 593-606 (2002-09-07)
Microsomal cytochromes P450 and tetrahydrobiopterin (BH4) free-NOS II catalyze the oxidation of N-hydroxyguanidines by NADPH and O2 with formation of nitrogen oxides including NO. These reactions are not selective in terms of substrates, as they occur on most N-hydroxyguanidines, and
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