B-NICOTYRINE Chemical Properties

Melting point:

168-169 °C

Boiling point:

78-80°C/0/15mm

Density 

1.2410

refractive index 

1.6057 (estimate)

storage temp. 

-20°C Freezer, Under Inert Atmosphere

solubility 

Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly), Met

form 

Oil

pka

pK1:4.76(+1) (25°C)

color 

Pale Yellow to Brown to Dark Orange

Stability:

Light, Air Sensitive

EPA Substance Registry System

Pyridine, 3-(1-methyl-1H-pyrrol-2-yl)- (487-19-4)

Safety Information

HS Code 

2939800000

B-NICOTYRINE Usage And Synthesis

Description

The occurrence of this alkaloid in the cigar type of tobacco has been reported by Wenusch and subsequently confirmed by Spath and Kesztler. It forms a colour_x0002_less oil when pure and yields crystalline salts and derivatives, e.g. the p1atinichloride, m.p. 158°C; picrate, m.p. 170-1 °c and the methiodide, m.p. 2l1-3°e. It may also be prepared from nicotine by oxidation with silver oxide, silver acetate or potassium ferricyanide. With Zn and HCI, the base is reduced to nicotine and 4:5-dihydronicotyrine, b.p. 244-6°C, yielding a dipicrate, m.p. l64°e. In the presence of prepared Pt02, the latter may be further reduced to dihydrometanicotine, the dipicrate of which has m.p. 161-2°C. Nicotyrine may be converted directly into nicotine in one operation by controlled hydrogenation in the presence on Pd-e

Chemical Properties

Clear Light Red-Brown Oil

Uses

Nicotryrine is an alkaloid derived from the dehydrogenation of nicotine and its analog, nornicotine. An alkaloid occurring in cigaret smoke.

Definition

ChEBI: Nicotyrine is a member of pyridines.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 2476, 1989 DOI: 10.1021/jo00271a052

References

Cahours, Etard., Bull. Soc. Chim. Fr., 34, 449 (1880)
Pictet, Crepieux., Ber., 28, 1904 (1895)
Pictet, Crepieux., ibid, 33, 2355 (1900)
Wibaut, Oberhoff., Rec. trav. Chim., 47,935 (1928)
Wenusch., Biochem. Zeit., 275,361 (1935)
Spath, Kesztler., Ber., 70,2450 (1937)
Spath, Wibaut, Kesztler., ibid, 71, 100 (1938)

B-NICOTYRINE(487-19-4)Related Product Information

• BETA-NICOTYRINE DIPICRATE
• 2,2'-Nicotyrine
• BETA-NICOTYRINE = 3-(1-METHYLPYRROL-2-YL)PYRIDINE
• N-BOC-B-NORNICOTRYINE
• 1-[2-(3,4-DIMETHOXY-PHENYL)-ETHYL]-2-METHYL-5-PYRIDIN-3-YL-1H-PYRROLE-3-CARBOXYLIC ACID
• 4-[2-(3-PYRIDINYL)-4,5-DIHYDROPYRROLO[3,2,1-HI]INDOL-1-YL]-1-BUTANAMINE OXALATE
• B-NICOTYRINE
• 3-(1-methyl-1H-pyrrol-2-yl)pyridine, compound with picric acid (1:2)
• AKOS 215-21