N3876
Sigma

(−)-Nicotine

≥99% (GC), liquid

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Synonym

(−)-1-Methyl-2-(3-pyridyl)pyrrolidine

Molecular Formula

C₁₀H₁₄N₂

Molecular Weight

162.23

CAS Number

54-11-5

Beilstein Registry Number

82109

MDL number

MFCD00006369

PubChem Substance ID

24897663

EG/EC Number

200-193-3

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Descriptions

Frequently Asked Questions

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Biochem/physiol Actions

Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.

Properties

assay

≥99% (GC)

form

liquid

optical activity

[α]20/D −169°(lit.)

color

yellow

refractive index

n20/D 1.5265(lit.)

solubility

ethanol: 50 mg/mL

density

1.010 g/mL at 20 °C(lit.)

Gene Information

human ... CHRNA2(1135)

References

Reference

Sihver, W., et al., Autoradiographic comparison of [³H](-)nicotine, [³H]cytisine and [³H]epibatidine binding in relation to vesicular acetylcholine transport sites in the temporal cortex in Alzheimer's disease. Neuroscience 94, 685-696, (1999)

Girod, R., et al., Heteromeric complexes of α5 and/or α7 subunits. Effects of calcium and potential role in nicotine-induced presynaptic facilitation. Ann. N.Y. Acad. Sci. 868, 578-590, (1999) abstract

Lena, C., and Changeux, J.P., Pathological mutations of nicotinic receptors and nicotine-based therapies for brain disorders. Curr. Opin. Neurobiol. 7, 674-682, (1997) abstract

Brioni, J.D., et al., The pharmacology of (−)-nicotine and novel cholinergic channel modulators. Adv. Pharmacol. 37, 153-214, (1997) abstract

Haass, M., and Kubler, W., Nicotine and sympathetic neurotransmission. Cardiovasc. Drugs Ther. 10, 657-665, (1997)

Merck

Merck 13,6551

Beilstein

Beil. 23,V,6,64

reference

Aldrich MSDS 1, 1349:A / Corp MSDS 1 (2), 2541:A / FT-IR 2 (3), 3756:D / FT-IR 1 (2), 768:B / FT-NMR 1 (3), 294:B / IR-Spectra (3), 1328:G / NMR-Reference 2 (2), 647:B / RegBook 1 (2), 2525:K / Sax 6, 1997 / Sigma FT-IR 1 (1), 596:D / Structure Index 1, 398:E:6 / Vapor Phase 3, 1537:B

Safety

Hazard Codes

T+,N

Risk Statements

25-27-51/53

Safety Statements

36/37-45-61

RIDADR

UN 1654 6.1/PG 2

WGK Germany

RTECS

QS5250000