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N3018

Sigma-Aldrich

(±)-Nornicotine

≥98% (TLC), liquid

Synonym(s):

2-(3-Pyridyl)pyrrolidine, 3-(2-Pyrrolidinyl)pyridine

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About This Item

Empirical Formula (Hill Notation):
C9H12N2
CAS Number:
5746-86-1
Molecular Weight:
148.20
Beilstein:
81968
MDL number:
MFCD00016913
UNSPSC Code:
12352210
eCl@ss:
39151701
PubChem Substance ID:
24897615
NACRES:
NA.77

Quality Level

200

Assay

≥98% (TLC)

form

liquid

color

yellow

solubility

H2O: 20 mg/mL

storage temp.

2-8°C

SMILES string

C1CNC(C1)c2cccnc2

InChI

1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2

InChI key

MYKUKUCHPMASKF-UHFFFAOYSA-N

Gene Information

mouse ... Chrna1(11435) , Chrna7(11441)
rat ... Chrna4(25590)

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Application

(±)-Nornicotine has been used as a neat alkaloid standard to demonstrate the mechanistic role that oxides of nitrogen have in tobacco-specific nitrosamines formation.

Biochem/physiol Actions

Nornicotine, an active metabolite of nicotine, is a nicotinic acetylcholine receptor agonist. Nornicotine is a minor alkaloid of tobacco leaves that serves as a precursor of a carcinogen, N-nitrosonornicotine. N-Demethylation of nicotine gives nornicotine, which occurs especially during tobacco leaf senescence and curing.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M T Bardo et al.
Psychopharmacology, 146(3), 290-296 (1999-12-14)
Nicotine is a tobacco alkaloid known to be important in the acquisition and maintenance of tobacco smoking. However, other constituents in tobacco may contribute to the dependence liability. The present report sought to determine whether nornicotine, a tobacco alkaloid and
L Teng et al.
The Journal of pharmacology and experimental therapeutics, 283(2), 778-787 (1997-11-14)
Previous results from our laboratory demonstrated that S(-)nornicotine, a major tobacco alkaloid and an active nicotine metabolite present in the CNS, increases dopamine release from rat striatal slices in a concentration-dependent and calcium-dependent manner. The present study determined if S(-)nornicotine-evoked
Wojciech Piekoszewski et al.
Przeglad lekarski, 66(10), 593-597 (2009-01-01)
The assay of biomarkers in biological material is the most popular and reliable method in estimate exposure to tobacco smoke. Nicotine and its metabolites qualify to the most specific biomarkers for tobacco smoke. Currently the most often used are cotinine
Joseph R Holtman et al.
Pharmacology, biochemistry, and behavior, 94(3), 352-362 (2009-10-06)
Neuronal nicotinic acetylcholinic receptors (nAChR) are promising targets for the development of novel analgesics. Nicotine and other nAChR-agonists produce profound analgesia in rodent models of acute and persistent pain. However, significant side-effects are of concern. Nornicotine (N-desmethyl-nicotine) appears to activate
Jennifer B Treweek et al.
Accounts of chemical research, 42(5), 659-669 (2009-03-12)
Nicotine and methamphetamine are frequently abused in modern society, despite the increasing evidence of their addictive, neuropharmacological, and toxic effects. Tobacco, the most widely abused substance, is the leading cause of preventable death in the United States, killing nearly half
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