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Key Documents

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N3018

Sigma-Aldrich

(±)-Nornicotine

≥98% (TLC), liquid

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C9H12N2
Número de CAS:
5746-86-1
Peso molecular:
148.20
Beilstein/REAXYS Number:
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

signalword

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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

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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
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
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
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
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