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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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25 MG
$211.50
50 MG
$405.00

$211.50

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Estimated to ship onApril 11, 2025


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25 MG
$211.50
50 MG
$405.00

About This Item

Empirical Formula (Hill Notation):
C9H12N2
CAS Number:
Molecular Weight:
148.20
Beilstein/REAXYS Number:
81968
MDL number:
UNSPSC Code:
12352210
eCl@ss:
39151701
PubChem Substance ID:
NACRES:
NA.77

$211.50

List Price$235.00Save 10%

Estimated to ship onApril 11, 2025


Request a Bulk Order

Quality Level

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

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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.

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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


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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
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
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

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