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Merck
CN

N1019

(−)-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
NACRES:
NA.77
PubChem Substance ID:
24897454
UNSPSC Code:
12352210
MDL number:
MFCD00148918

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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

SMILES string

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

InChI key

IECQULMJVNSKDB-RCWTXCDDSA-N

assay

≥95% (TLC)

form

liquid

concentration

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

color

dark brown

Quality Level

100

Gene Information

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

Related Categories

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.

Analysis Note

Mixture of nicotine base and nicotine sulfate.

Disclaimer

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

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk

WGK 3

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3801
MKCS5785
MKCR4926
MKCR5458
MKCL3355

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Explorations of Plant?s Chemodiversity: Role of Nitrogen-Containing Secondary Metabolites in Plant Defense
Molecular Aspects of Plant-Pathogen Interaction, 309-332 (2018)
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
Behavioural evidence for self-medication in bumblebees
Baracchi D, et al.
F1000Research, 4(1) (2015)
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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