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Basic Information
CAS No.: 494-97-3
Name: NORNICOTINE, DL-(RG)
Molecular Structure:
Molecular Structure of 494-97-3 (NORNICOTINE, DL-(RG))
Formula: C9H12N2
Molecular Weight: 148.208
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;
Density: 1.043g/cm3
Boiling Point: 269.999°C at 760 mmHg
Flash Point: 111.291°C
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 NOx.
PSA: 24.92000
LogP: 1.83490
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With Chiralpak AD-H In methanol; N,N-dimethyl-ethanamine Resolution of racemate;A 30%
B 25%
Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In water at 28℃; for 120h; Product distribution; Cunninghamella echinulata IFO-4444; other times, other fungi;
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  • (S)-3-(Pyrrolidin-2-yl)pyridine494-97-3

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    494-97-3

    (S)-3-(Pyrrolidin-2-yl)pyridine494-97-3

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  • NORNICOTINE

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    NORNICOTINE

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    NORNICOTINE, DL-(RG)

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  • Nicotine EP IMP F (nornicotine )

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    494-97-3

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    494-97-3

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  • NORNICOTINE, DL-(RG) CAS No.494-97-3

  • Casno:

    494-97-3

    NORNICOTINE, DL-(RG) CAS No.494-97-3

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Chemistry

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

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect 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.

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 NOx.

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 .