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N8381

Sigma-Aldrich

2-Naphthylamine

powder

Synonym(s):

β-Naphthylamine, 2-Aminonaphthalene

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About This Item

Linear Formula:
C10H7NH2
CAS Number:
91-59-8
Molecular Weight:
143.19
Beilstein:
3939429
EC Number:
202-080-4
MDL number:
MFCD00004112
UNSPSC Code:
12352103
PubChem Substance ID:
24897863
NACRES:
NA.25

form

powder

bp

306 °C (lit.)

mp

111-113 °C (lit.)

density

1.061 g/mL at 25 °C (lit.)

SMILES string

Nc1ccc2ccccc2c1

InChI

1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2

InChI key

JBIJLHTVPXGSAM-UHFFFAOYSA-N

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General description

2-Naphthylamine is a bladder carcinogen, which is mainly present in cigarette smoke.

Application

2-Naphthylamine has been used as a substrate for measuring aminopeptidase A and aminopeptidase N activity.

Biochem/physiol Actions

Environmental carcinogen; induces bladder cancer.

Signal Word

Danger

Hazard Statements

H302,H350,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 1A

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Y Yasunaga et al.
Laboratory investigation; a journal of technical methods and pathology, 77(6), 677-684 (1998-01-14)
Epidemiologic studies have revealed an increased risk for development of transitional cell carcinoma (TCC) among dye workers/painters occupationally exposed to aromatic amines such as benzidine, beta-naphthylamine, orthotoluidine, and aniline. In the present study, p53 gene mutations in 26 patients with
Shiho Ohnishi et al.
Japanese journal of cancer research : Gann, 93(7), 736-743 (2002-08-01)
2-Naphthylamine (2-NA), a bladder carcinogen, is contained in cigarette smoke. DNA adduct formation is thought to be a major cause of DNA damage by carcinogenic aromatic amines. We have investigated whether a metabolite of 2-NA, 2-nitroso-1-naphthol (NO-naphthol) causes oxidative DNA
A Fernández-Atucha et al.
Biology of sex differences, 8, 5-5 (2017-02-09)
Serum peptidases, such as angiotensin-converting enzyme (ACE), angiotensin-converting enzyme-2 (ACE2), neutral endopeptidase (NEP), aminopeptidase N (APN), and aminopeptidase A (APA), are important elements of the renin-angiotensin system (RAS). Dysregulation of these enzymes has been associated with hypertension and cardiovascular risk.
Carlos de la Haba et al.
Biochimica et biophysica acta, 1838(1 Pt B), 148-157 (2013-08-21)
Receptor-ligand binding is an essential interaction for biological function. Oxidative stress can modify receptors and/or membrane lipid dynamics, thus altering cell physiological functions. The aim of this study is to analyze how oxidative stress may alter receptor-ligand binding and lipid
Carlos de la Haba et al.
Biochimica et biophysica acta, 1828(2), 357-364 (2012-09-04)
Plasma membrane is one of the preferential targets of reactive oxygen species which cause lipid peroxidation. This process modifies membrane properties such as membrane fluidity, a very important physical feature known to modulate membrane protein localization and function. The aim
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