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N-075

Supelco

(±)-N′-Nitrosonornicotine (NNN) solution

1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®

Synonym(s):

NNN, NNN solution

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About This Item

Empirical Formula (Hill Notation):
C9H11N3O
CAS Number:
80508-23-2
Molecular Weight:
177.20
UNSPSC Code:
41116107
NACRES:
NA.24

grade

certified reference material

Quality Level

300

form

liquid

feature

Snap-N-Spike®/Snap-N-Shoot®

packaging

ampule of 1 mL

manufacturer/tradename

Cerilliant®

concentration

1.0 mg/mL in methanol

technique(s)

gas chromatography (GC): suitable
liquid chromatography (LC): suitable

application(s)

forensics and toxicology

format

single component solution

storage temp.

−20°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, also known as NNN, is a nitrosamine and potential carcinogen found in a variety of tobacco products including snuff, cigarettes, chewing tobacco, and cigars. Certified Spiking Solutions® are suitable for use in nicotine testing or environmental monitoring by LC-MS/MS or GC/MS.

Legal Information

CERILLIANT is a registered trademark of Merck KGaA, Darmstadt, Germany
CERTIFIED SPIKING SOLUTIONS is a registered trademark of Merck KGaA, Darmstadt, Germany
Snap-N-Shoot is a registered trademark of Cerilliant Corporation
Snap-N-Spike is a registered trademark of Merck KGaA, Darmstadt, Germany

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signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

target_organs

Eyes

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

51.8 °F - closed cup

flash_point_c

11.0 °C - closed cup

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Ariane Nunes-Alves et al.
Journal of molecular neuroscience : MN, 49(1), 52-61 (2012-08-01)
Nitrosamines are well known for their carcinogenic potential. Recently, it was found that some of them may also interact with human nicotinic acetylcholine receptor (nAChR) subtypes. This work studied the effects of N-nitrosonornicotine (NNN) on recombinant rat α3β4 nAChR in
Irina Stepanov et al.
Cancer research, 69(21), 8236-8240 (2009-10-22)
N'-nitrosonornicotine (NNN) is a strong carcinogen present in unburned tobacco and cigarette smoke. We here analyze data obtained in two studies, in which a biomarker of exposure to NNN--the sum of NNN and its pyridine-N-glucuronide, called total NNN--was quantified in
Li Li et al.
Chemical research in toxicology, 22(8), 1464-1472 (2009-07-16)
Tobacco-specific nitrosamines, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N'-nitrosonornicotine, are considered to be human carcinogens. Both compounds are metabolized to pyridyloxobutylating intermediates that react with DNA to form adducts such as 7-[4-(3-pyridyl)-4-oxobut-1-yl]guanine, O(2)-[4-(3-pyridyl)-4-oxobut-1-yl]cytosine, O(2)-[4-(3-pyridyl)-4-oxobut-1-yl]-2'-deoxythymidine (O(2)-pobdT), O(6)-[4-(3-pyridyl)-4-oxobut-1-yl]-2'-deoxyguanosine (O(6)-pobdG), and 4-hydroxy-1-(3-pyridyl)-1-butanone-releasing adducts. The role of specific
Major tobacco companies have technology to reduce carcinogen levels but do not apply it to popular smokeless tobacco products.
Stephen S Hecht et al.
Tobacco control, 20(6), 443-443 (2010-10-12)
John M Prins et al.
Journal of proteome research, 12(3), 1282-1288 (2013-01-12)
The association of tobacco smoke with decreased cell motility and wound healing is well documented; however, the cellular mechanisms and specific toxic tobacco constituents responsible for this effect are not well understood. Tobacco-specific N-nitrosamines (TSNAs) are among the most important
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