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N3018

Sigma-Aldrich

(±)-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
Beilstein/REAXYS Number:
81968
MDL number:
MFCD00016913
UNSPSC Code:
12352210
eCl@ss:
39151701
PubChem Substance ID:
24897615
NACRES:
NA.77

Key Documents

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Product Name

(±)-Nornicotine, ≥98% (TLC), liquid

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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This Item
N3876SML1236N1019
(±)-Nornicotine ≥98% (TLC), liquid

Sigma-Aldrich

N3018

(±)-Nornicotine

(−)-Nicotine ≥99% (GC), liquid

Sigma-Aldrich

N3876

(−)-Nicotine

(−)-Nicotine hydrogen tartrate salt ≥98% (HPLC)

Sigma-Aldrich

SML1236

(−)-Nicotine hydrogen tartrate salt

(−)-Nicotine hemisulfate salt ≥95% (TLC), ~35 % (w/v) in H2O (based on free base)

Sigma-Aldrich

N1019

(−)-Nicotine hemisulfate salt

form

liquid

form

liquid

form

powder

form

liquid

assay

≥98% (TLC)

assay

≥99% (GC)

assay

≥98% (HPLC)

assay

≥95% (TLC)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

-

storage temp.

room temp

storage temp.

-

solubility

H2O: 20 mg/mL

solubility

ethanol: 50 mg/mL

solubility

H2O: 20 mg/mL, clear

solubility

-

color

yellow

color

yellow

color

white to beige

color

dark brown

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000465982
0000465982
0000404007
0000410716
0000410716

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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
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
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
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