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SML1236

Sigma-Aldrich

(−)-Nicotine hydrogen tartrate salt

≥98% (HPLC)

Synonym(s):

(−)-Nicotine ditartrate, (−)-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:
12352210
PubChem Substance ID:
329825736
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +20 to +26°, c = 1.0 in water

storage condition

desiccated

color

white to beige

solubility

H2O: 20 mg/mL, clear

storage temp.

room temp

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

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Application

(−)-Nicotine hydrogen tartrate salt has been used as an agonist for acetylcholine receptor (AChr).
(−)-Nicotine hydrogen tartrate salt has been used in intracellular calcium imaging.

Biochem/physiol Actions

NHT is considered to be more stable than nicotine. Nicotine is highly addictive drug and is indirectly but strongly associated with tobacco related diseases. It helps to discontinue smoking. Nicotine might serve as a therapeutic agent in treating Alzheimer’s disease, Parkinson’s disease and ulcerative colitis.
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

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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Mahmoud M Farag et al.
European journal of pharmacology, 720(1-3), 1-6 (2013-11-12)
The aim of this study was to evaluate the effects of chronic nicotine administration on bone mineral homeostasis in rapidly growing young rats in comparison to effects in adult male rats. Two doses of nicotine (3 and 4.5mg/kg/day, as nicotine
Metabolism and disposition kinetics of nicotine.
Hukkanen J, et al.
Pharmacological Reviews, 57(1), 79-115 (2005)
Nicotine hydrogen tartrate loaded chitosan nanoparticles: Formulation, characterization and in vitro delivery from dry powder inhaler formulation.
Wang H, et al.
European Journal of Pharmaceutics and Biopharmaceutics, 113, 118-131 (2017)
All muscarinic acetylcholine receptors (M 1-M 5) are expressed in murine brain microvascular endothelium.
Radu B M, et al.
Scientific Reports, 7(1), 5083-5083 (2017)
Ozra Dehkordi et al.
Journal of neuroscience research, 93(2), 230-243 (2014-09-17)
Direct actions of nicotine in the CNS appear to be essential for its reinforcing properties. However, activation of nicotinic acetylcholine receptors (nAChRs) on afferent sensory nerve fibers is an important component of addiction to, and withdrawal from, cigarette smoking. The
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