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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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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
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
François Marclay et al.
Forensic science international, 213(1-3), 73-84 (2011-07-02)
Tobacco consumption is a global epidemic responsible for a vast burden of disease. With pharmacological properties sought-after by consumers and responsible for addiction issues, nicotine is the main reason of this phenomenon. Accordingly, smokeless tobacco products are of growing popularity
Delphine Calas-List et al.
Neuroscience letters, 518(1), 64-68 (2012-05-15)
The goal of the present study is to examine the agonist action of nornicotine on insect nicotinic acetylcholine receptors. Using patch-clamp techniques on cockroach dorsal unpaired median neurons, we demonstrated that nornicotine induced two distinct ionic currents named types 1
Snehal Jadey et al.
The Journal of general physiology, 141(1), 95-104 (2013-01-02)
A primary target for nicotine is the acetylcholine receptor channel (AChR). Some of the ability of nicotine to activate differentially AChR subtypes has been traced to a transmitter-binding site amino acid that is glycine in lower affinity and lysine in
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