CAS 16543-55-8

N-Nitrosonornicotine

Description:

N-Nitrosonornicotine (CAS 16543-55-8) is a nitrosamine derivative of the tobacco alkaloid nornicotine. It is characterized by its molecular structure, which includes a nitroso group (-N=O) attached to the nornicotine backbone. This compound is of significant interest in toxicology and cancer research due to its potential carcinogenic properties, particularly in relation to tobacco use. N-Nitrosonornicotine is known to exhibit mutagenic effects, which can lead to DNA damage and contribute to the development of various cancers. It is typically found in tobacco products and is formed during the curing and processing of tobacco leaves. The substance is a colorless to pale yellow liquid and is soluble in organic solvents. Its stability can be influenced by environmental factors such as temperature and pH. Due to its toxicological implications, N-nitrosonornicotine is subject to regulatory scrutiny, and research continues to explore its mechanisms of action and effects on human health.

Formula: C₉H₁₁N₃O

InChI: 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/t9-/m0/s1

InChI key: InChIKey=XKABJYQDMJTNGQ-VIFPVBQESA-N

SMILES: N(=O)N1[C@@H](CCC1)C=2C=CC=NC2

Synonyms:

• (S)-N′-Nitrosonornicotine
• 1-Nitroso-2-(3-Pyridyl)Pyrrolidine
• 1’-Demethyl-1’-Nitroso-Nicotin
• 1’-Desmethyl-1’-Nitrosonicotine
• 1’-Nitroso-1’-Demethyl-Nicotin
• 1’-Nitroso-1’-Demethylnicotine
• 1’-Nitrosonornicotine
• 3-(1-Nitrosopyrrolidin-2-Yl)Pyridine
• 3-[(2S)-1-Nitroso-2-pyrrolidinyl]pyridine
• 3-[(2S)-1-Nitrosopyrrolidin-2-yl]pyridine
• NNN
• Nicotine, 1′-demethyl-1′-nitroso-
• Nitrosonornicotine
• Nornicotine, N-nitroso-
• Pyridine, 3-(1-nitroso-2-pyrrolidinyl)-, (S)-
• Pyridine, 3-[(2S)-1-nitroso-2-pyrrolidinyl]-
• anti-N′-Nitrosonornicotine

N'-Nitrosonornicotine

CAS: 16543-55-8

Color and Shape: Neat

Ref: 86-MM0517.27

(2S)-N'-Nitrosonornicotine

CAS: 16543-55-8

Stability Hygroscopic
Applications A tobacco alkaloid as risk factor of human cancer.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Stepanov, I., et al.: Cancer Res., 69, 8236 (2009), Maertens, R., et al.: Chem. Res. Toxicol., 22, 1406 (2009), Gaworski, C., et al.: Toxicol., 269, 54 (2010),

Formula: C₉H₁₁N₃O

Color and Shape: Light Yellow

Molecular weight: 177.20

Ref: TR-N535001

(2S)-N’-Nitrosonornicotine

CAS: 16543-55-8

(2S)-N’-Nitrosonornicotine is a tobacco-specific nitrosamine that has been shown to be carcinogenic in the experimental model. It has been found to inhibit the activity of liver microsomes, which are enzymes that break down drugs in the body. The pharmacokinetic properties of (2S)-N’-Nitrosonornicotine have been studied in rats and mice, but not humans. It has been shown that it is metabolized by methylation and ethylation, with nicotine being its major metabolite.

Formula: C₉H₁₁N₃O

Purity: Min. 95%

Color and Shape: Beige Slightly Yellow Powder

Molecular weight: 177.2 g/mol

Ref: 3D-FN153274

(2S)-N’-Nitrosonornicotine

CAS: 16543-55-8

Formula: C₉H₁₁N₃O

Molecular weight: 177.21

Ref: ST-EA-CP-NIT100

N-Nitrosonornicotine

CAS: 16543-55-8

N-Nitrosonornicotine, a tobacco-specific nitrosamine, exhibits carcinogenic and mutagenic properties, and is capable of inducing micronuclei in C3A cells. Additionally, N-Nitrosonornicotine can form DNA adducts.

Formula: C₉H₁₁N₃O

Color and Shape: Solid

Molecular weight: 177.2

Ref: TM-T201694