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Cas Database

Name	Nornicotine	EINECS	N/A
CAS No.	494-97-3	Density	1.043g/cm³
PSA	24.92000	LogP	1.83490
Solubility	N/A	Melting Point	N/A
Formula	C₉H₁₂N₂	Boiling Point	269.999°C at 760 mmHg
Molecular Weight	148.208	Flash Point	111.291°C
Transport Information	N/A	Appearance	N/A
Safety	Poison by intraperitoneal and intravenous routes. About 1/3 the toxicity of nicotine. Causes faintness, prostration, muscular weakness, severe nausea, vomiting, diarrhea, and collapse without convulsions. An insecticide. When heated to decomposition it emits highly toxic fumes of NO_x.	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	(S)-Nornicotine;Pyridine, 3-(2-pyrrolidinyl)-, (S)-;3-(2S)-2-pyrrolidinylpyridine;3-(2-Pyrrolidinyl)pyridine;3-[(2S)-pyrrolidin-2-yl]pyridine;(S)-3-(Pyrrolidin-2-yl)pyridine;	Article Data	26

Nornicotine Synthetic route

: 252005-64-4
(S)-1-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(3-pyridyl)pyrrolidine

A: 135865-76-8, 135865-81-5, 144102-44-3, 148968-87-0, 150737-36-3
2,3,4,6-Tetra-O-pivaloyl-α/β-D-galactopyranose

B: 494-97-3
nornicotine

Conditions

Conditions	Yield
In hydrogenchloride; methanol Hydrolysis;	A n/a B 95%

: 314280-29-0
(S)-3-(1-azido-but-3-enyl)pyridine

: 494-97-3
nornicotine

Conditions

Conditions	Yield
With bis(cyclohexanyl)borane In tetrahydrofuran at -15 - 20℃; for 12h;	85%

: (S)-5-bromonornicotine (R)-(+)-α-methoxy-α-trifluoromethylphenyl acetic acid salt

: 494-97-3
nornicotine

Conditions

Conditions	Yield
Stage #1: (S)-5-bromonornicotine (R)-(+)-α-methoxy-α-trifluoromethylphenyl acetic acid salt With potassium hydroxide In water for 1h; Stage #2: With palladium 10% on activated carbon; hydrogen; triethylamine In ethanol at 20℃;	69%

: 5746-86-1
rac-nornicotine

: 494-97-3
nornicotine

Conditions

Conditions	Yield
With borane-ammonia complex; 6-hydroxy-D-nicotine oxidase E350L/E352D mutant for 28h; Kinetics; Enzymatic reaction; enantioselective reaction;	60%
With 6,6′-dinitro[1,1′-biphenyl]-2,2′-dicarboxylic acid

: 54-11-5
nicotin

: 494-97-3
nornicotine

Conditions

Conditions	Yield
bioconversion, by cell suspension of Nicotiana plumbaginifolia;	53.2%
With potassium permanganate
With water; silver(l) oxide

: (S)-5-bromonornicotine (+)-MTPA

: 494-97-3
nornicotine

Conditions

Conditions	Yield
Stage #1: (S)-5-bromonornicotine (+)-MTPA With potassium hydroxide In diethyl ether Stage #2: With palladium 10% on activated carbon; hydrogen; triethylamine In ethanol for 1h;	53%

: 5746-86-1
rac-nornicotine

A: 494-97-3
nornicotine

B: 7076-23-5
(+)-nornicotine

Conditions

Conditions	Yield
With Chiralpak AD-H In methanol; N,N-dimethyl-ethanamine Resolution of racemate;	A 30% B 25%

: 54-11-5
nicotin

A: 494-97-3
nornicotine

B: 5980-06-3
S-(-)-Norcotinine

C: 486-56-6
cotinine

D: 491-26-9, 29419-54-3, 29419-55-4, 51020-67-8, 51095-86-4, 63551-14-4
Nicotine-N-oxide

Conditions

Conditions	Yield
With air; cofactor solution; phenobarbitone-induced rabbit hepatic homogenate In phosphate buffer at 37℃; for 1h; pH=7.4; Oxidation; demethylation; Further byproducts given;	A 15.9% B n/a C 27.5% D n/a

: 83023-58-9
(S)-5-bromo-3-(1H-2-pyrrolidinyl)pyridine

: 494-97-3
nornicotine

Conditions

Conditions	Yield
With triethylamine; palladium on activated charcoal In ethanol under 760 Torr; for 1h; Yield given;
With hydrogen
With hydrogen; triethylamine; palladium on activated charcoal In ethanol under 760.051 Torr; for 1h;	621 mg

: 54-11-5
nicotin

A: 525-74-6
N-methylmyosmine

B: 494-97-3
nornicotine

Conditions

Conditions	Yield
In water at 28℃; for 120h; Product distribution; Cunninghamella echinulata IFO-4444; other times, other fungi;

Nornicotine Chemical Properties

Empirical Formula: C₉H₁₂N₂
Molecular Weight: 148.205 g/mol
Index of Refraction: 1.536
Density: 1.042 g/cm³
Flash Point: 111.3 °C
Enthalpy of Vaporization: 50.82 kJ/mol
Boiling Point: 270 °C at 760 mmHg
Vapour Pressure: 0.00702 mmHg at 25 °C
Structure of Nornicotine (CAS NO.494-97-3):

IUPAC Name of Nornicotine (CAS NO.494-97-3): 3-Pyrrolidin-2-ylpyridine
Product Categories of Nornicotine (CAS NO.494-97-3): Pharmacetical

Nornicotine Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intraperitoneal	14660ug/kg (14.66mg/kg)	Nara Igaku Zasshi. Journal of the Nara Medical Association. Vol. 8, Pg. 69, 1957.
mouse	LD50	intravenous	3409ug/kg (3.409mg/kg)	Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 82, 1946.
rabbit	LD50	intraperitoneal	> 13700ug/kg (13.7mg/kg)	Proceedings of the Society for Experimental Biology and Medicine. Vol. 58, Pg. 231, 1945.
rabbit	LD50	intravenous	3mg/kg (3mg/kg)	Proceedings of the Society for Experimental Biology and Medicine. Vol. 58, Pg. 231, 1945.
rat	LDLo	intraperitoneal	23500ug/kg (23.5mg/kg)	"Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 1061, 1989.

Nornicotine Safety Profile

Poison by intraperitoneal and intravenous routes. About 1/3 the toxicity of nicotine. Causes faintness, prostration, muscular weakness, severe nausea, vomiting, diarrhea, and collapse without convulsions. An insecticide. When heated to decomposition it emits highly toxic fumes of NO_x.

Nornicotine Specification

Nornicotine ,its cas register number is 494-97-3. It also can be called 3-(2-Pyrrolidinyl)pyridine ; Pyridine, 3-(2-pyrrolidinyl)- ;and 3-(Pyrrolidin-2-yl)pyridine .

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