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717436

Sigma-Aldrich

Benzamide oxime

97%

Synonym(s):

N-Hydroxybenzamide

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About This Item

Empirical Formula (Hill Notation):
C7H8N2O
CAS Number:
613-92-3
Molecular Weight:
136.15
EC Number:
210-361-8
MDL number:
MFCD00474011
UNSPSC Code:
12352100
PubChem Substance ID:
329763488
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

74-78 °C

functional group

amine
oxime
phenyl

SMILES string

N\C(=N\O)c1ccccc1

InChI

1S/C7H8N2O/c8-7(9-10)6-4-2-1-3-5-6/h1-5,10H,(H2,8,9)

InChI key

MXOQNVMDKHLYCZ-UHFFFAOYSA-N

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM3112
MKBT6790V
MKBC3660

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B Clement et al.
Molecular pharmacology, 43(3), 335-342 (1993-03-01)
Previous investigations have provided evidence for the participation of the cytochrome P-450 (P-450) enzyme system in the established N-hydroxylation of benzamidine to benzamidoxime by microsomal fractions from rabbit liver homogenates. In the present investigation, a representative mixture of P-450 isoenzymes
B Clement et al.
Xenobiotica; the fate of foreign compounds in biological systems, 17(6), 659-667 (1987-06-01)
1. A simple and fast h.p.l.c. analysis of benzamidoxime formed by microsomal N-hydroxylation of benzamidine is presented which is well suited for the determination of the N-oxygenation activity of microsomal enzymes. 2. Optimal reaction conditions were determined. The apparent Km
A Jousserandot et al.
Biochemistry, 37(49), 17179-17191 (1998-12-23)
Oxidation by rat liver microsomes of 13 compounds involving a C=N(OH) function (including N-hydroxyguanidines, amidoximes, ketoximes, and aldoximes) was found to occur with the release of nitrogen oxides such as NO, NO2-, and NO3-. The greatest activities were observed with
A K Fröhlich et al.
Xenobiotica; the fate of foreign compounds in biological systems, 35(1), 17-25 (2005-03-25)
N-Hydroxyamidines (amidoximes) can act as pro-drugs of amidines (e.g. ximelagatran, a novel direct thrombin inhibitor). This known pro-drug principle is based on the N-reduction of an oral bioavailable amidoxime to its active form. Previous study of the metabolism of the
B Clement et al.
Archiv der Pharmazie, 322(7), 431-435 (1989-07-01)
At pH 7.4 neither benzamidine (1) is ring-hydroxylated nor benzamidoxime (2) is N-hydroxylated, reduced or ring-hydroxylated by aerobic incubations with microsomal fractions (12000 g supernatant, microsomes) of rabbit liver homogenates and NADPH. Products of hydrolytic processes are also not detected.
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