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D8015

Sigma-Aldrich

4-Dimethylaminoantipyrine

reactive nitrogen species scavenger

Synonym(s):

4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one, Aminopyrine

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About This Item

Empirical Formula (Hill Notation):
C13H17N3O
CAS Number:
58-15-1
Molecular Weight:
231.29
EC Number:
200-365-8
MDL number:
MFCD00003142
UNSPSC Code:
12352116
PubChem Substance ID:
24894178
NACRES:
NA.77

form

solid

mp

107-109 °C (lit.)

SMILES string

CN(C)C1=C(C)N(C)N(c2ccccc2)C1=O

InChI

1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3

InChI key

RMMXTBMQSGEXHJ-UHFFFAOYSA-N

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Application

Oxidation by Fe(VI) has potential to remove N-nitrosodiumethylamine precursors, including 4-dimethylaminoantipyrine, from drinking water. 4-Dimethylaminoantipyrine is itself an effective scavenger of reactive nitrogen compounds nitric oxide and peroxynitrite, important in the inflammatory response.

Biochem/physiol Actions

Antipyrine was found to be nonmutagenic when screened against Salmonella typhimurium tester strains TA100, TA98, TA97, TA102 and TA104.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Giacomo Russo et al.
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Arthur G Roberts et al.
Biochemistry, 50(12), 2123-2134 (2011-03-08)
To understand the molecular basis of sequential N-dealkylation by cytochrome P450 2B enzymes, we studied the binding of amidopyrine (AP) as well as the metabolites of this reaction, desmethylamidopyrine (DMAP) and aminoantipyrine (AAP), using the X-ray crystal structure of rabbit
Alba Rocco et al.
Journal of hepatology, 56(4), 782-787 (2011-12-17)
Although numerous non-invasive tests are currently available to explore liver function and disease activity in patients with HCV-related chronic diseases, none of these indicate the likelihood of disease progression in the individual patient. We aimed at assessing the prognostic ability
Dipak Samanta et al.
Chemical communications (Cambridge, England), 48(17), 2298-2300 (2012-01-24)
Three-component self-assembly of a cis-blocked 90° Pd(II) acceptor with a mixture of a tetraimidazole and a linear dipyridyl donor self-discriminated into unusual Pd(8) molecular swing (1) and Pd(6) molecular boat (2), which are characterized by single-crystal X-ray diffraction analysis; their
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