140198

Sigma-Aldrich

Formamidoxime

99%

Linear Formula:
HC(=NOH)NH2
CAS Number:
Molecular Weight:
60.06
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

assay

99%

mp

112-115 °C (lit.)

storage temp.

2-8°C

SMILES string

N\C=N\O

InChI

1S/CH4N2O/c2-1-3-4/h1,4H,(H2,2,3)

InChI key

IONSZLINWCGRRI-UHFFFAOYSA-N

Application

Formamidoxime may be used as inhibitor of DNA synthesis.

Packaging

5 g in glass bottle

Biochem/physiol Actions

Formamidoxime undergoes oxidative cleavage of C==N bonds in tracheal smooth muscle cells catalyzed by liver cytochrome P450 producing NO. It inhibits replicative DNA synthesis. It has antitumor activity against L1210 leukemia.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

F R Althaus et al.
The Journal of biological chemistry, 256(24), 13079-13084 (1981-12-25)
Microsomal proteins from cultured chick embryo hepatocytes were separated by polyacrylamide gel electrophoresis and their rate constants of degradation (Kd) were estimated using double isotope techniques. The proteins were found to be heterogeneous in their turnover rates, proteins, or subunits...
Weiwen Zhao et al.
Organic & biomolecular chemistry, 9(22), 7647-7651 (2011-09-29)
The formamidoxime configurational Z isomer coupled with the pyridylbiscarboxamide conformational codon were used to fold planar, curved structures. When embedded into macrocycles, this folded motif promotes dimerization through π-π stacking and hydrogen-bonding and the formation of tubules akin to molecular...
K P Flora et al.
Cancer research, 38(5), 1291-1295 (1978-05-01)
A series of amidoximes was prepared and evaluated for possible antitumor activity against L1210 leukemia. Three of the most active compounds in the L1210 system, formamidoxime, acetamidoxime, and 2-aminoacetamidoxime hydrochloride, were also active against P388 leukemia. Acetamidoxime was marginally active...
Yi Yan et al.
Chemical communications (Cambridge, England), 48(63), 7829-7831 (2012-07-04)
The partial positive charge of amide protons is used to promote macrocyclization and form crown-ether analogs. Their deprotonation generates very selective pH-switchable alkaline earth ion receptors only in the presence of an appropriate substrate.
Y Jia et al.
The American journal of physiology, 275(5 Pt 1), L895-L901 (1998-11-14)
Nitric oxide (NO) is known to be synthesized from L-arginine in a reaction catalyzed by NO synthase. Liver cytochrome P-450 enzymes also catalyze the oxidative cleavage of C==N bonds of compounds containing a -C(NH2)==NOH function, producing NO in vitro. The...

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