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Merck
CN

N3018

(±)-Nornicotine

≥98% (TLC), Nicotinic acetylcholine receptor agonist, 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
UNSPSC Code:
12352210
eCl@ss:
39151701
PubChem Substance ID:
24897615
NACRES:
NA.77
Beilstein/REAXYS Number:
81968
MDL number:
MFCD00016913

Key Documents

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Product Name

(±)-Nornicotine, ≥98% (TLC), liquid

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

assay

≥98% (TLC)

form

liquid

color

yellow

solubility

H2O: 20 mg/mL

storage temp.

2-8°C

Quality Level

200

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000492567
0000492567
0000465982
0000465982
0000404007

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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
Bingfang Yue et al.
Methods in molecular biology (Clifton, N.J.), 603, 389-398 (2010-01-16)
We describe a method for the quantitative analysis of nicotine, cotinine, trans-3'-hydroxy cotinine, nornicotine, and anabasine in urine, serum, and plasma using liquid chromatography-tandem mass spectrometry. A mix of deuterium-labeled internal standards (IS) is added to a specimen aliquot. The
Chiu-Yueh Hung et al.
Plant physiology, 161(2), 1049-1060 (2012-12-12)
Methylenetetrahydrofolate reductase (MTHFR) is a key enzyme of the tetrahydrofolate (THF)-mediated one-carbon (C1) metabolic network. This enzyme catalyzes the reduction of 5,10-methylene-THF to 5-methyl-THF. The latter donates its methyl group to homocysteine, forming methionine, which is then used for the
Phattharaporn Pakdeechanuan et al.
Plant & cell physiology, 53(12), 2038-2046 (2012-10-05)
Nornicotine is formed from nicotine by nicotine N-demethylase, a CYP82E family monooxygenase, and accumulates to high levels in some tobacco (Nicotiana tabacum) cultivars and many wild Nicotiana species. Nicotiana langsdorffii does not form nornicotine, whereas the closely related species N.
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