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59773

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

analytical standard

Synonym(s):

NNAL

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10 MG

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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

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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

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

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

4-(Methylnitrosoamino)-1-(3-pyridinyl)-1-butanone analytical standard

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78013

4-(Methylnitrosoamino)-1-(3-pyridinyl)-1-butanone

4-(Methyl-d3-nitrosamino)-1-(3-pyridyl)-1-butanol analytical standard

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94454

4-(Methyl-d3-nitrosamino)-1-(3-pyridyl)-1-butanol

N′-Nitrosonornicotine analytical standard

Supelco

75285

N′-Nitrosonornicotine

technique(s)

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

technique(s)

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

technique(s)

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

technique(s)

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

format

neat

format

neat

format

neat

format

neat

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

grade

analytical standard

grade

analytical standard

grade

analytical standard

grade

analytical standard

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

assay

≥92.0% (TLC)

assay

≥98.0% (GC)

assay

≥97.0% (HPLC)

assay

≥99.0% (HPLC)

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. [1]

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)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCM3174
BCCK6481
BCCG9820
BCCG1059
BCCF4339

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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
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
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 M Leslie et al.
The Journal of biological chemistry, 276(30), 27846-27854 (2001-05-29)
Nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and its metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) play a crucial role in the induction of lung cancer, and NNAL-O-glucuronide formation and elimination are important steps in detoxification of these compounds. In the present study, we investigated the ATP-binding cassette
S S Hecht et al.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 4(8), 877-884 (1995-12-01)
Epidemiological studies indicate that vegetable consumption protects against lung cancer in humans, but the protective constituents have not been identified. Phenethyl isothiocyanate (PEITC), which is release upon chewing of watercress (nasturtium officinale), is a chemopreventive agent against lung cancer induced
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