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N5260

Sigma-Aldrich

(−)-Nicotine hydrogen tartrate salt

≥98% (TLC), powder

Synonym(s):

(−)-1-Methyl-2-(3-pyridyl)pyrrolidine (+)-bitartrate salt

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About This Item

Empirical Formula (Hill Notation):
C10H14N2 · 2C4H6O6
CAS Number:
65-31-6
Molecular Weight:
462.41
EC Number:
200-607-2
UNSPSC Code:
12352200
PubChem Substance ID:
24278591

Assay

≥98% (TLC)

form

powder

color

white to off-white

solubility

H2O: 50 mg/mL

SMILES string

CN1CCC[C@H]1C2=CC=CN=C2.C

InChI

1S/C10H14N2.CH4/c1-12-7-3-5-10(12)9-4-2-6-11-8-9;/h2,4,6,8,10H,3,5,7H2,1H3;1H4/t10-;/m0./s1

InChI key

RYYKFQGHMYGLEL-PPHPATTJSA-N

Gene Information

human ... CHRNA1(1134) , CHRNA10(57053) , CHRNA2(1135) , CHRNA3(1136) , CHRNA4(1137) , CHRNA5(1138) , CHRNA6(8973) , CHRNA7(1139) , CHRNA9(55584) , CHRNB1(1140) , CHRNB2(1141) , CHRNB3(1142) , CHRNB4(1143)

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Biochem/physiol Actions

Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.

Signal Word

Danger

Hazard Statements

H301,H319,H330,H361d,H411

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 2

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

289.8 °F

Flash Point(C)

143.2 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nicotine for system suitability European Pharmacopoeia (EP) Reference Standard

Y0001023

Nicotine for system suitability

(−)-Nicotine PESTANAL®, analytical standard

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36733

(−)-Nicotine

Jhodie R Duncan et al.
Journal of applied physiology (Bethesda, Md. : 1985), 107(5), 1579-1590 (2009-09-05)
During pregnancy, exposure to nicotine and other compounds in cigarette smoke increases the risk of the sudden infant death syndrome (SIDS) two- to fivefold. Serotonergic (5-HT) abnormalities are found, in infants who die of SIDS, in regions of the medulla
Adam J Prus et al.
Pharmacology, biochemistry, and behavior, 91(1), 150-154 (2008-07-23)
The Lewis (LEW) strain of rat appears more sensitive to nicotine than other strains in self-administration, conditioned place preference, and drug discrimination behavioral studies. The present study sought to further evaluate the behavioral effects of chronic nicotine treatment in the
Anthony Renda et al.
BMC neuroscience, 15, 89-89 (2014-07-21)
Understanding the underlying causes of nicotine addiction will require a multidisciplinary approach examining the key molecular, cellular and neuronal circuit functional changes that drive escalating levels of nicotine self-administration. In this study, we examined whether mice pretreated with chronic nicotine
Song Xue et al.
Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco, 22(2), 172-179 (2018-11-20)
Tobacco is highly addictive, and after the development of dependence, it is difficult to quit smoking. Therefore, it is important to understand the factors that play a role in the initiation of smoking. The rewarding effects of nicotine play a
Jonathan D Raybuck et al.
Behavioral neuroscience, 122(5), 1166-1171 (2008-10-01)
Varenicline, a partial agonist for a4ss2 nicotinic acetylcholine receptors (nAChRs) and full agonist for a7 nAChRs, has been approved for the treatment of smoking cessation. Although recent clinical trials support the efficacy of varenicline for managing global nicotine withdrawal symptoms
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