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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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Product Name

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol, analytical standard

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

Analysis Note

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

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.

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.

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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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
S G Carmella et al.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 4(6), 635-642 (1995-09-01)
This study describes quantitation in smokers' urine of two metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). The metabolites are 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL), which is also a lung carcinogen, and its O-glucuronide (NNAL-Gluc), a presumed detoxification product of NNK. Using updated
G M Lackmann et al.
Journal of the National Cancer Institute, 91(5), 459-465 (1999-03-10)
Cigarette smoking during pregnancy can result in fetal exposure to carcinogens that are transferred from the mother via the placenta, but little information is available on fetal uptake of such compounds. We analyzed samples of the first urine from newborns
Transport of the ?-O-Glucuronide Conjugate of the Tobacco-specific Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by the Multidrug Resistance Protein 1 (MRP1) REQUIREMENT FOR GLUTATHIONE OR A NON-SULFUR-CONTAINING ANALOG
Leslie.ME, et al.
The Journal of Biological Chemistry, 276(30), 27846-27854 (2001)
Yuya Kawasaki et al.
Genes and environment : the official journal of the Japanese Environmental Mutagen Society, 42, 26-26 (2020-09-19)
Urinary nicotine and cotinine levels are often measured as biomarkers for tobacco smoke exposure. However, these biomarkers are not appropriate to evaluate the effects of quitting smoking for several days, because of their short half-lives. In this study, we focused
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