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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/REAXYS Number:
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.

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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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
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.
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
Dylan M Owen et al.
Nature communications, 3, 1256-1256 (2012-12-06)
Lipid microdomains are postulated to regulate many membrane-associated processes but have remained highly controversial. Here we provide the first direct evidence that the plasma membrane of intact, live cells is comprised of a sub-resolution mixture of approximately 76% ordered and
Joanna M Kwiatek et al.
PloS one, 8(2), e52960-e52960 (2013-02-08)
Visualization and quantification of lipid order is an important tool in membrane biophysics and cell biology, but the availability of environmentally sensitive fluorescent membrane probes is limited. Here, we present the characterization of the novel fluorescent dyes PY3304, PY3174 and
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