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(+/-)-NICOTINE

CAS No.
22083-74-5
Chemical Name:
(+/-)-NICOTINE
Synonyms
NICOTINE;(r,s)-nicotine;rac-Nicotine;1-METHYL-2-(3-PYRIDYL)PYRROLIDINE;Nicotine for system suitability CRS;dl-nicotine;(+-)-pyridin;(+-)-nicotin;BLACK LEAF 40;(+/-)-NICOTINE
CBNumber:
CB2459639
Molecular Formula:
C10H14N2
Molecular Weight:
162.23
MDL Number:
MFCD00065370
MOL File:
22083-74-5.mol
Last updated:2023-05-18 11:31:03

(+/-)-NICOTINE Properties

Melting point -79 °C
Boiling point 67°C/0.5 mm
Density 1.02 g/mL at 25 °C(lit.)
Flash point 101 °C
storage temp. Refrigerator
solubility ethanol: 50 mg/mL
pka 8.02(at 25℃)
form liquid
color yellow
optical activity [α]25/D 0°(lit.)
BRN 82108
Stability Air Sensitive
CAS DataBase Reference 22083-74-5(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS09
Signal word  Danger
Hazard statements  H301-H310-H411
Precautionary statements  P262-P264-P273-P280-P301+P310-P302+P352+P310
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  3
RTECS  QS5257500
NFPA 704
1
3 0

(+/-)-NICOTINE Chemical Properties,Uses,Production

Chemical Properties

(+/-)-NICOTINE is Colourless Liquid

Uses

This is the unnatural isomer of Nicotine

Uses

(+/-)-NICOTINE is an alkaloid isolated from plants. It is an active stimulant, having both addictive and carcinogenic properties.

Uses

Nicotine is an alkaloid isolated from plants. Nicotine is an active stimulant, having both addictive and carcinogenic properties. Nicotine can be absorbed through the alimentary canal, respiratory tra ct and intact skin. Nicotine is used in the treatment of smoking withdrawal syndrome. Nicotine has been used as an anthelmintic.

Definition

ChEBI: 3-(1-methylpyrrolidin-2-yl)pyridine is an N-alkylpyrrolidine that consists of N-methylpyrrolidine bearing a pyridin-3-yl substituent at position 2. It is a N-alkylpyrrolidine, a pyridine alkaloid and a pyrrolidine alkaloid.

Biochem/physiol Actions

Prototype nicotinic acetylcholine receptor agonist.

Purification Methods

(+/-)-NICOTINE is purified by fractional distillation. Its solubility in EtOH is ~5%. The picrate forms yellow needles from hot H2O and has m 219o. The methiodide has m 219o (from MeOH). [Craig J Am Chem Soc 55 2854 1933, Nakane & Hutchinson J Org Chem 43 3922 1978, Beilstein 23/6 V 64.] POISONOUS.

50-00-0
64-18-6
5746-86-1
22083-74-5
Synthesis of (+/-)-NICOTINE from Formaldehyde and Formic acid and 3-(2-Pyrrolidinyl)pyridine
BLACK LEAF 40 (+/-)-NICOTINE 3-(1-methyl-2-pyrrolidinyl)-pyridin 3-(1-methyl-pyrrolidin-2-yl)-pyridine (±)-Nicotine-d7 (+-)-nicotin (+-)-pyridin (+)-3-[(2R)-1-Methyl-2-pyrrolidinyl]pyridine (2R)-1-Methyl-2-(3-pyridyl)pyrrolidine 3-[(2R)-1-Methyl-2-pyrrolidinyl]pyridine dl-beta-nicotine dl-nicotine (-)-1-Methyl-2-[3-pyridyl]pyrrolidine, free base R-(+)-Nicotine, [+]-1-Methyl-2-[3-pyridyl]pyrrolidine, Free Base NICOTINE ALKALOID 95% NICOTINE ALKALOID USP DL-Nicotine-d3 (N-methyl-d3) Nicotine salts: (d1-beta-Nicotine: DL-Nicotine) (+/-)-NICOTINE USP/EP/BP (+/-)-NICOTINE Nicotine for system suitability CRS rac-Nicotine (r,s)-nicotine NICOTINE 1-METHYL-2-(3-PYRIDYL)PYRROLIDINE Acrylamide Impurity 19 22083-74-5 Ligand-Gated Ion Channels BioChemical Cell Biology Cell Signaling and Neuroscience Nicotinic Acetylcholine Receptor Modulators Ion Channels AgonistsIon Channels Cholinergics Ligand-Gated Ion Channels Neurotransmitters Nicotinic Acetylcholine Receptor Modulators Nicotine Derivatives Neurochemicals