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Key Documents

N1019

Sigma-Aldrich

(−)-Nicotine hemisulfate salt

≥95% (TLC), ~35 % (w/v) in H2O (based on free base)

Synonym(s):

(−)-1-Methyl-2-(3-pyridyl)pyrrolidine

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About This Item

Linear Formula:
(C10H14N2)2 · H2SO4
CAS Number:
65-30-5
Molecular Weight:
422.54
MDL number:
MFCD00148918
UNSPSC Code:
12352210
PubChem Substance ID:
24897454
NACRES:
NA.77

Quality Level

100

Assay

≥95% (TLC)

form

liquid

concentration

~35 % (w/v) in H2O (based on free base)

color

dark brown

SMILES string

OS(O)(=O)=O.CN1CCC[C@H]1c2cccnc2.CN3CCC[C@H]3c4cccnc4

InChI

1S/2C10H14N2.H2O4S/c2*1-12-7-3-5-10(12)9-4-2-6-11-8-9;1-5(2,3)4/h2*2,4,6,8,10H,3,5,7H2,1H3;(H2,1,2,3,4)/t2*10-;/m00./s1

InChI key

IECQULMJVNSKDB-RCWTXCDDSA-N

Gene Information

human ... CHRNA4(1137) , CHRNB2(1141)

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General description

Nicotine is found in the leaves of Nicotiana species. It binds to nicotinic acetylcholine receptors and inhibits endogenous neurotransmitters. Nicotine is associated with lung cancer development and reduces the efficiency of chemotherapeutic agents. It is used to treat Alzheimer′s and Parkinson′s disease.

Application

(−)-Nicotine hemisulfate salt has been used to study the influence of nicotine on the severity of choroidal neovascularization (CNV). It also has been used as a natural nectar alkaloid to study the effect of self-medication in bumblebees.

Biochem/physiol Actions

Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.

Quality

Mixture of nicotine base and nicotine sulfate.

Caution

Shelf-life of the solution as supplied is at least six years when stored at room temperature.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301 - H310 + H330 - H411

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Certificates of Analysis (COA)

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Behavioural evidence for self-medication in bumblebees
Baracchi D, et al.
F1000Research, 4(1) (2015)
Nicotine increases size and severity of experimental choroidal neovascularization
Suner IJ, et al.
Investigative Ophthalmology & Visual Science, 45(1), 311-317 (2004)
Caiqi Zhao et al.
Cell discovery, 3, 17009-17009 (2017-05-23)
Vagal circuits-α7 nAChR (α7 nicotinic acetylcholine receptor, coded by
Explorations of Plant?s Chemodiversity: Role of Nitrogen-Containing Secondary Metabolites in Plant Defense
Molecular Aspects of Plant-Pathogen Interaction, 309-332 (2018)
Nicotine inactivation of the proapoptotic function of Bax through phosphorylation
Xin M and Deng X
The Journal of Biological Chemistry, 280(11), 10781-10789 (2005)
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