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Merck
CN

59773

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol

analytical standard

Synonym(s):

NNAL

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About This Item

Empirical Formula (Hill Notation):
C10H15N3O2
CAS Number:
76014-81-8
Molecular Weight:
209.25
NACRES:
NA.24
PubChem Substance ID:
329758717
UNSPSC Code:
41116107
MDL number:
MFCD00870462

Key Documents

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InChI

1S/C10H15N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8,10,14H,3,5,7H2,1H3

SMILES string

CN(N=O)CCCC(O)C1=CN=CC=C1

InChI key

OGRXKBUCZFFSTL-UHFFFAOYSA-N

grade

analytical standard

assay

≥92.0% (TLC)

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

technique(s)

HPLC: suitable, gas chromatography (GC): suitable, solid phase extraction (SPE): suitable

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

storage temp.

2-8°C

Quality Level

100

Related Categories

General description

Nitrosamines are chemical compounds that can form during drug manufacturing and may pose health risks, including carcinogenicity.
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol is commonly employed as a reference compound in analytical chemistry. It is utilized in chromatographic and spectrometric techniques for the detection and quantification of nitrosamines in chemical, pharmaceutical, and environmental matrices.

Application

It may be used as an analytical reference standard for the determination of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol in urine of nonsmokers and smokers using liquid chromatography/tandem mass spectrometry.

Analysis Note

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3174
BCCK6481
BCCG9820
BCCG1059
BCCF4339

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M E Staretz et al.
Drug metabolism and disposition: the biological fate of chemicals, 25(2), 154-162 (1997-02-01)
We compared the metabolism in human hepatic microsomes of three tobacco smoke carcinogens believed to be involved in the induction of cancer in humans: benzo[a]pyrene (BaP),4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), and N'-nitrosonomicotine (NNN). The metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL), a major metabolite of NNK
Steven G Carmella et al.
Chemical research in toxicology, 15(4), 545-550 (2002-04-16)
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is a tobacco-specific lung carcinogen which may play an important role as a cause of lung cancer in smokers. NNK is extensively metabolized to 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL), which like NNK is a potent pulmonary carcinogen. NNAL in turn is
Sung Hoon Jeong et al.
Scientific reports, 11(1), 4536-4536 (2021-02-27)
Children are at risk of exposure to secondhand smoke. We aimed to evaluate the extent of their exposure to it in relation to their parents' smoking status by using biomarkers relevant to smoking. We evaluated 847 school-age children (6-12 years) who
Yi Wang et al.
Cancer prevention research (Philadelphia, Pa.), 13(5), 483-492 (2020-02-28)
Tobacco smoking is the primary risk factor for lung cancer, driven by the addictive nature of nicotine and the indisputable carcinogenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) as well as other compounds. The integration of lung cancer chemoprevention with smoking cessation is one
E Richter et al.
Toxicology, 144(1-3), 83-91 (2000-04-27)
The pharmacokinetics of in vitro metabolism of the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK; concentration range 0.03-250 microM) and its proximal metabolite, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL; 0.04-250 microM), were determined in Syrian golden hamster liver, lung, and kidney tissue slices in organ culture under
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