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N′-Nitrosonornicotine

analytical standard

Synonym(s):

1-Nitroso-2-(3-pyridyl)pyrrolidine, 3-(1-Nitroso-2-pyrrolidinyl)pyridine, NNN

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About This Item

Empirical Formula (Hill Notation):
C9H11N3O
CAS Number:
80508-23-2
Molecular Weight:
177.20
MDL number:
MFCD00274581
UNSPSC Code:
41116107
PubChem Substance ID:
329766318
NACRES:
NA.24

grade

analytical standard

Quality Level

100

assay

≥99.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

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

SMILES string

O=NN1CCCC1c2cccnc2

InChI

1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2

InChI key

XKABJYQDMJTNGQ-UHFFFAOYSA-N

Related Categories

General description

N′-Nitrosonornicotine is a tobacco specific nitrosamine, which is found to be carcinogenic in nature. It is produced via nitrosation of nicotine during the process of curing, aging, processing and smoking of tobacco.

Application

N′-Nitrosonornicotine may be used as an analytical reference standard for the quantification of the analyte in biological samples using liquid chromatography coupled with tandem mass spectrometry.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK5634
BCCK1178
BCCG5567
BCCG5217
BCCC9591

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≥98% (TLC), liquid

Sigma-Aldrich

N3018

(±)-Nornicotine

USP

USP

1463337

Nicotine Related Compound B

97%

Sigma-Aldrich

139505

2-(2-Aminoethyl)-1-methylpyrrolidine

98 atom % D

Sigma-Aldrich

451797

Benzo[a]pyrene-d12

Supelco

Supelco

47537-U

52 Component Indoor Air Standard

Benzene-d6 "100%", 99.96 atom % D

Sigma-Aldrich

175870

Benzene-d6

≥99% (GC), liquid

Sigma-Aldrich

N3876

(−)-Nicotine

Evidence for cytochrome P450 2A6 and 3A4 as major catalysts for N'-nitrosonornicotine alpha-hydroxylation by human liver microsomes
Patten JC, et al.
Carcinogenesis, 18(8), 1623-1630 (1997)
Simultaneous determination of four tobacco-specific N-nitrosamines (TSNA) in human urine
Kavvadias D, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 877(11-12), 1185-1192 (2009)
Sultana Shahana Banu et al.
International journal for parasitology, 49(7), 555-567 (2019-05-21)
In the Indian subcontinent, infection with Leishmania donovani can cause fatal visceral leishmaniasis. Genetic variation in L. donovani is believed to occur rapidly from environmental changes and through selective drug pressures, thereby allowing continued disease occurrence in this region. All
Huda Mahmoud et al.
Frontiers in microbiology, 8, 2063-2063 (2017-11-09)
Corals that naturally thrive under extreme conditions are gaining increasing attention due to their importance as living models to understand the impact of global warming on world corals. Here, we present the first metagenomic study of viral communities in corals
Julia Heger-Stevic et al.
PLoS pathogens, 14(12), e1007488-e1007488 (2018-12-20)
Hepatitis B virus (HBV) replicates its 3 kb DNA genome through capsid-internal reverse transcription, initiated by assembly of 120 core protein (HBc) dimers around a complex of viral pregenomic (pg) RNA and polymerase. Following synthesis of relaxed circular (RC) DNA
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