Product Name

  • Name

    NORNICOTINE, DL-(RG)

  • EINECS
  • CAS No. 494-97-3
  • Article Data26
  • CAS DataBase
  • Density 1.043g/cm3
  • Solubility
  • Melting Point
  • Formula C9H12N2
  • Boiling Point 269.999°C at 760 mmHg
  • Molecular Weight 148.208
  • Flash Point 111.291°C
  • Transport Information
  • Appearance
  • 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.
  • Risk Codes
  • Molecular Structure Molecular Structure of 494-97-3 (NORNICOTINE, DL-(RG))
  • Hazard Symbols
  • 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;
  • PSA 24.92000
  • LogP 1.83490

Synthetic route

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

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

A

2,3,4,6-Tetra-O-pivaloyl-α/β-D-galactopyranose
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

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
In hydrogenchloride; methanol Hydrolysis;A n/a
B 95%
(S)-3-(1-azido-but-3-enyl)pyridine
314280-29-0

(S)-3-(1-azido-but-3-enyl)pyridine

nornicotine
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

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

nornicotine
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%
rac-nornicotine
5746-86-1

rac-nornicotine

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
nicotin
54-11-5

nicotin

nornicotine
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

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

nornicotine
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%
rac-nornicotine
5746-86-1

rac-nornicotine

A

nornicotine
494-97-3

nornicotine

B

(+)-nornicotine
7076-23-5

(+)-nornicotine

Conditions
ConditionsYield
With Chiralpak AD-H In methanol; N,N-dimethyl-ethanamine Resolution of racemate;A 30%
B 25%
nicotin
54-11-5

nicotin

A

nornicotine
494-97-3

nornicotine

B

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

S-(-)-Norcotinine

C

cotinine
486-56-6

cotinine

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

(S)-5-bromo-3-(1H-2-pyrrolidinyl)pyridine

nornicotine
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
nicotin
54-11-5

nicotin

A

N-methylmyosmine
525-74-6

N-methylmyosmine

B

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
In water at 28℃; for 120h; Product distribution; Cunninghamella echinulata IFO-4444; other times, other fungi;
nicotin
54-11-5

nicotin

A

N-formyl-2-(3-pyridyl)pyrrolidine
38840-03-8

N-formyl-2-(3-pyridyl)pyrrolidine

B

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
at 25℃; Nicotiana tabacum L. cv Wisconsin-38;
1-(N-methyl)-1,5-pentanediamine
32752-52-6

1-(N-methyl)-1,5-pentanediamine

A

N-methylanabasine
24380-92-5

N-methylanabasine

B

nornicotine
494-97-3

nornicotine

C

nicotin
54-11-5

nicotin

D

anatabine
581-49-7

anatabine

Conditions
ConditionsYield
With Nicotiana rustica Condensation; Enzymatic reaction; Further byproducts given;
N-ethylcadaverine
258818-11-0

N-ethylcadaverine

A

N-ethylanabasine
68245-76-1

N-ethylanabasine

B

nornicotine
494-97-3

nornicotine

C

nicotin
54-11-5

nicotin

D

anatabine
581-49-7

anatabine

Conditions
ConditionsYield
With Nicotiana rustica Condensation; Enzymatic reaction; Further byproducts given;
N-(4-aminobutyl)propylamine
70862-18-9

N-(4-aminobutyl)propylamine

A

nornicotine
494-97-3

nornicotine

B

nicotin
54-11-5

nicotin

C

anatabine
581-49-7

anatabine

D

N'-Propylnornicotine

N'-Propylnornicotine

Conditions
ConditionsYield
With Nicotiana rustica Condensation; Enzymatic reaction; Further byproducts given;
N-(4-aminobutyl)butylamine
70862-19-0

N-(4-aminobutyl)butylamine

A

nornicotine
494-97-3

nornicotine

B

nicotin
54-11-5

nicotin

C

anatabine
581-49-7

anatabine

D

N-n-butylnornicotine

N-n-butylnornicotine

Conditions
ConditionsYield
With Nicotiana rustica Condensation; Enzymatic reaction; Further byproducts given;
N-propylcadaverine

N-propylcadaverine

A

N-propylanabasine
68245-77-2

N-propylanabasine

B

nornicotine
494-97-3

nornicotine

C

nicotin
54-11-5

nicotin

D

anatabine
581-49-7

anatabine

Conditions
ConditionsYield
With Nicotiana rustica Condensation; Enzymatic reaction; Further byproducts given;
5-bromopyridine-3-carbaldehyde
113118-81-3

5-bromopyridine-3-carbaldehyde

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 97 percent / Zn / tetrahydrofuran / 1 h / 20 °C
2: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C
3: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C
4: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
5: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C
6: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
7: H2
View Scheme
Multi-step reaction with 6 steps
1.1: DMP / CH2Cl2
1.2: tetrahydrofuran
2.1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C
3.1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
4.1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C
5.1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
6.1: H2
View Scheme
Multi-step reaction with 5 steps
1: diethyl ether / 1 h / -100 °C
2: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
3: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C
4: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
5: H2
View Scheme
5-bromo-3-pyridinecarboxylic acid
20826-04-4

5-bromo-3-pyridinecarboxylic acid

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: DMF; oxalyl chloride / acetonitrile; tetrahydrofuran; pyridine / 1.5 h / -30 °C
1.2: 63 percent / CuI; tri-tert-butoxyaluminium hydride / acetonitrile; tetrahydrofuran; pyridine / 0.25 h / -78 °C
2.1: 97 percent / Zn / tetrahydrofuran / 1 h / 20 °C
3.1: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C
4.1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C
5.1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
6.1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C
7.1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
8.1: H2
View Scheme
Multi-step reaction with 7 steps
1.1: DMF; oxalyl chloride / acetonitrile; tetrahydrofuran; pyridine / 1.5 h / -30 °C
1.2: 63 percent / CuI; tri-tert-butoxyaluminium hydride / acetonitrile; tetrahydrofuran; pyridine / 0.25 h / -78 °C
2.1: DMP / CH2Cl2
2.2: tetrahydrofuran
3.1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C
4.1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
5.1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C
6.1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
7.1: H2
View Scheme
Multi-step reaction with 6 steps
1.1: DMF; oxalyl chloride / acetonitrile; tetrahydrofuran; pyridine / 1.5 h / -30 °C
1.2: 63 percent / CuI; tri-tert-butoxyaluminium hydride / acetonitrile; tetrahydrofuran; pyridine / 0.25 h / -78 °C
2.1: diethyl ether / 1 h / -100 °C
3.1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
4.1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C
5.1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
6.1: H2
View Scheme
1-(5-bromopyridin-3-yl)but-3-en-1-ol
360767-43-7

1-(5-bromopyridin-3-yl)but-3-en-1-ol

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C
2: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C
3: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
4: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C
5: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
6: H2
View Scheme
1-(5-bromopyridin-3-yl)but-3-en-1-one
360767-46-0

1-(5-bromopyridin-3-yl)but-3-en-1-one

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C
2: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
3: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C
4: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
5: H2
View Scheme
(R)-1-(5-bromopyridin-3-yl)but-3-en-1-ol
360767-40-4

(R)-1-(5-bromopyridin-3-yl)but-3-en-1-ol

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
2: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C
3: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
4: H2
View Scheme
(S)-3-(1-azidobut-3-enyl)-5-bromopyridine
360767-36-8

(S)-3-(1-azidobut-3-enyl)-5-bromopyridine

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
2: H2
View Scheme
(R)-methanesulfonic acid 1-(5-bromopyridin-3-yl)but-3-enyl ester
360767-38-0

(R)-methanesulfonic acid 1-(5-bromopyridin-3-yl)but-3-enyl ester

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C
2: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C
3: H2
View Scheme
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrahydrofuran / 1 h / -100 °C
2: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
3: 97 percent / NaN3 / dimethylformamide / 4 h / 60 °C
4: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: tetrahydrofuran / 1 h / -100 °C
2: 88 percent / diphenylphosphorylazide; DBU / toluene / 72 h / 20 °C
3: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C
View Scheme
(R)-1-(pyridin-3-yl)but-3-en-1-ol
314280-28-9

(R)-1-(pyridin-3-yl)but-3-en-1-ol

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C
2: 97 percent / NaN3 / dimethylformamide / 4 h / 60 °C
3: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 88 percent / diphenylphosphorylazide; DBU / toluene / 72 h / 20 °C
2: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C
View Scheme
(R)-methanesulfonic acid 1-pyridin-3-yl-but-3-enyl ester
372519-16-9

(R)-methanesulfonic acid 1-pyridin-3-yl-but-3-enyl ester

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 97 percent / NaN3 / dimethylformamide / 4 h / 60 °C
2: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C
View Scheme
4-(3-pyridyl)-4-oxobutanol
59578-62-0

4-(3-pyridyl)-4-oxobutanol

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 82 percent / (COCl)2; NEt3 / dimethylsulfoxide
2.1: molecular sieves 4 Angstroem / CH2Cl2 / 16 h / 20 °C
2.2: 45 percent / NaCNBH3 / methanol; acetic acid / 16 h / 0 - 20 °C
3.1: 95 percent / aq. HCl; methanol
View Scheme
4-Oxo-1-(3-pyridyl)-1-butanone
76014-80-7

4-Oxo-1-(3-pyridyl)-1-butanone

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: molecular sieves 4 Angstroem / CH2Cl2 / 16 h / 20 °C
1.2: 45 percent / NaCNBH3 / methanol; acetic acid / 16 h / 0 - 20 °C
2.1: 95 percent / aq. HCl; methanol
View Scheme
ethyl 5-bromo-3-pyridinecarboxylate
20986-40-7

ethyl 5-bromo-3-pyridinecarboxylate

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
2: 79 percent / NaBH4 / methanol; acetic acid / -40 - -20 °C
4: Et3N / 10percent Pd/C / ethanol / 1 h / 760 Torr
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydride / tetrahydrofuran
2.1: sodium tetrahydroborate; acetic acid; methanol
2.2: Resolution of racemate
3.1: potassium hydroxide / diethyl ether
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydride / mineral oil; hexane; tetrahydrofuran / 1 h / Reflux; Inert atmosphere
1.2: Reflux
2.1: acetic acid; sodium tetrahydroborate / methanol; acetonitrile / 0.17 h / -40 - 20 °C
3.1: ethyl acetate / 0.25 h
4.1: potassium hydroxide / diethyl ether
4.2: 1 h
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / Reflux; Inert atmosphere
1.2: Reflux; Inert atmosphere
2.1: acetic acid; sodium tetrahydroborate / methanol / 0.5 h / -40 - 20 °C
3.1: ethyl acetate / 0.25 h / 20 °C
4.1: potassium hydroxide / water / 1 h
4.2: 20 °C
View Scheme
5-Bromo-3-(2-pyrrolidinyl)pyridine
71719-06-7

5-Bromo-3-(2-pyrrolidinyl)pyridine

nornicotine
494-97-3

nornicotine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: Et3N / 10percent Pd/C / ethanol / 1 h / 760 Torr
View Scheme
Multi-step reaction with 2 steps
1.1: ethyl acetate / 0.25 h
2.1: potassium hydroxide / diethyl ether
2.2: 1 h
View Scheme
Multi-step reaction with 2 steps
1.1: ethyl acetate / 0.25 h / 20 °C
2.1: potassium hydroxide / water / 1 h
2.2: 20 °C
View Scheme
methyl 4-iodobutanoate
14273-85-9

methyl 4-iodobutanoate

nornicotine
494-97-3

nornicotine

(S)-methyl 4-(2-(pyridin-3-yl)pyrrolidin-1-yl)butanoate

(S)-methyl 4-(2-(pyridin-3-yl)pyrrolidin-1-yl)butanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h;78%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h;78%
methyl 6-iodohexanoate
14273-91-7

methyl 6-iodohexanoate

nornicotine
494-97-3

nornicotine

(S)-methyl 6-(2-(pyridin-3-yl)pyrrolidin-1-yl)hexanoate

(S)-methyl 6-(2-(pyridin-3-yl)pyrrolidin-1-yl)hexanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h;75%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h;75%
4-(4-bromo-2-chloro-phenoxy)-benzaldehyde
1040051-31-7

4-(4-bromo-2-chloro-phenoxy)-benzaldehyde

nornicotine
494-97-3

nornicotine

C22H20BrClN2O

C22H20BrClN2O

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 15h; Inert atmosphere;74%
methyl trans-γ-iodocrotonate
65495-78-5

methyl trans-γ-iodocrotonate

nornicotine
494-97-3

nornicotine

methyl (E)-4-((S)-2-(pyridin-3-yl)pyrrolidin-1-yl)but-2-enoate

methyl (E)-4-((S)-2-(pyridin-3-yl)pyrrolidin-1-yl)but-2-enoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h;73%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h;73%
3-chloro-4-(4-formylphenoxy)benzamide
676494-59-0

3-chloro-4-(4-formylphenoxy)benzamide

nornicotine
494-97-3

nornicotine

(S)-3-chloro-4-(4-((2-(pyridin-3-yl)pyrrolidin-1-yl)methyl)phenoxy)benzamide
1346133-08-1

(S)-3-chloro-4-(4-((2-(pyridin-3-yl)pyrrolidin-1-yl)methyl)phenoxy)benzamide

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃;68%
(6-iodohexyl)-carbamic acid 1,1-dimethylethyl ester
172846-36-5

(6-iodohexyl)-carbamic acid 1,1-dimethylethyl ester

nornicotine
494-97-3

nornicotine

[6-[(2S)-2-(3-pyridinyl)-1-pyrrolidinyl]hexyl]-carbamic acid 1,1-dimethylethyl ester
350820-82-5

[6-[(2S)-2-(3-pyridinyl)-1-pyrrolidinyl]hexyl]-carbamic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 15h;59%
benzyl 4-iodobutanoate
118058-69-8

benzyl 4-iodobutanoate

nornicotine
494-97-3

nornicotine

(2S)-2-(3-pyridinyl)-1-pyrrolidinebutanoic acid phenylmethyl ester
350820-86-9

(2S)-2-(3-pyridinyl)-1-pyrrolidinebutanoic acid phenylmethyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;58%
N-(tert-butoxycarbonyl)piperidine-4-carboxylic acid N-(4-iodobutyl)amide

N-(tert-butoxycarbonyl)piperidine-4-carboxylic acid N-(4-iodobutyl)amide

nornicotine
494-97-3

nornicotine

N-(tert-butoxycarbonyl)piperidine-4-carboxylic acid N-(4-((S)-2-(pyridin-3-yl)pyrrolidin-1-yl)butyl)amide

N-(tert-butoxycarbonyl)piperidine-4-carboxylic acid N-(4-((S)-2-(pyridin-3-yl)pyrrolidin-1-yl)butyl)amide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h;51%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h;51%
tert-butyl 4-((5-iodopentyl)carbamoyl)piperidine-1-carboxylate

tert-butyl 4-((5-iodopentyl)carbamoyl)piperidine-1-carboxylate

nornicotine
494-97-3

nornicotine

(S)-tert-butyl 4-((5-(2-(pyridin-3-yl)pyrrolidin-1-yl)pentyl)carbamoyl)piperidine-1-carboxylate

(S)-tert-butyl 4-((5-(2-(pyridin-3-yl)pyrrolidin-1-yl)pentyl)carbamoyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h;49%

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) 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.

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 NOx.

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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