(±)-nicotine

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Names

[ CAS No. ]:
22083-74-5

[ Name ]:
(±)-nicotine

[Synonym ]:
vrzjvuppqwdfac-yhyxmxqvsa
(R,S)-nicotine
(RS)-nicotine
3-(1-Methyl-2-pyrrolidinyl)pyridine
fdhr
3-(1-methyl-2-pyrrolidinyl)-Pyridine
1-Methyl-2-(3-pyridyl)pyrrolidine
MFCD00065370
(+/-)-nicotine
Pyridine, 3-(1-methyl-2-pyrrolidinyl)-
Pyridine, 3-(1-methyl-2-pyrrolidinyl)- (9CI)
(±)-3-(1-Methyl-2-pyrrolidinyl)pyridine
DL-Nicotine
(±)-nicotine
3-(1-Methylpyrrolidin-2-yl)pyridine
Nicotine

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
244.4±28.0 °C at 760 mmHg

[ Melting Point ]:
-79ºC

[ Molecular Formula ]:
C₁₀H₁₄N₂

[ Molecular Weight ]:
162.232

[ Flash Point ]:
101.7±0.0 °C

[ Exact Mass ]:
162.115692

[ PSA ]:
16.13000

[ LogP ]:
0.72

[ Appearance of Characters ]:
liquid | yellow

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.539

[ Storage condition ]:
Refrigerator

[ Water Solubility ]:
ethanol: 50 mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QS5257500

CHEMICAL NAME :: Nicotine, (+-)-

CAS REGISTRY NUMBER :: 22083-74-5

BEILSTEIN REFERENCE NO. :: 0082111

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C10-H14-N2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 31250 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 50,93,1934

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 50,93,1934

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 50,93,1934

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 15 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 50,93,1934

Safety Information

[ Symbol ]:

GHS06, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H310-H411

[ Precautionary Statements ]:
P273-P280-P301 + P310-P302 + P350-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
T+: Very toxic;N: Dangerous for the environment;

[ Risk Phrases ]:
25-27-51/53

[ Safety Phrases ]:
36/37-45-61

[ RIDADR ]:
UN 1654 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
QS5257500

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

Formaldehyde
(±)-Nornicotine
Formic Acid
(+)-Nicotine
(R,S)-1-METHYL-3-NICOTINOYLPYRROLIDONE
methylamine
4-oxo-4-(3-pyridinebutanal)
(RS) 1-methyl-2-(3'-pyridyl)pyrrolidine-2-carbaldehyde

DownStream

methylamine
3-(1-Methyl-1H-pyrrol-2-yl)pyridine
1-Methylpyrrolidine
L-Nicotine
(+)-Nicotine
Myosmine
1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone
Pyridine, 3-(3,4-dihydro-2-methoxy-2H-pyrrol-5-yl)
(±)-Nornicotine

Articles

Effects of environmental enrichment on ERK1/2 phosphorylation in the rat prefrontal cortex following nicotine-induced sensitization or nicotine self-administration.

Eur. J. Neurosci. 41(1) , 109-19, (2015)

Rats raised in an enriched condition (EC) exhibit alterations in the neurobiological and behavioral response to nicotine compared with rats reared in an impoverished condition (IC) or a standard condi...

Effects of maternal nicotine exposure on thyroid hormone metabolism and function in adult rat progeny.

J. Endocrinol. 224(3) , 315-25, (2015)

Postnatal nicotine exposure leads to obesity and hypothyroidism in adulthood. We studied the effects of maternal nicotine exposure during lactation on thyroid hormone (TH) metabolism and function in a...

A critical role for the melanocortin 4 receptor in stress-induced relapse to nicotine seeking in rats.

Addict. Biol. 20(2) , 324-35, (2015)

Tobacco addiction is characterized by a lack of control over smoking and relapse after periods of abstinence. Smoking cessation leads to a dysphoric state that contributes to relapse to smoking. After...