Nornicotine

• 2 - (3 -pyridyl ) pyrrolidine
• 3 - (2 -pyrrolidinyl ) pyridine
• 1'- Demethylnicotin

• 494-97-3 [( S)- nornicotine ]
• 7076-23-5 [(R) - nornicotine ]
• 5746-86-1 [( RS)- nornicotine ]

Yellow liquid

Liquid

1.0737 (19 ° C)

• 270 ° C
• 116-120 ° C ( 0.67 hPa)

Soluble in water (50 mg · ml -1)

1.5378 ( 18 ° C)

Attention

Template: Infobox chemical / molecular formula search available

Nornicotine is a chemical compound from the group of alkaloids. Their structure is derived from that of the nicotinic, which additionally has a methyl group on the nitrogen atom of the pyrrolidine ring.

Occurrence

Nornicotine occurs naturally in some types of tobacco. Here it is formed by the enzymatic degradation of nicotine.

Production

For the synthesis of nornicotine several avenues to explore. This includes the demethylation of nicotine. The cleavage of the methyl group can be accomplished for example by reaction with silver oxide.

The reduction of 3- myosmine example, with molecular hydrogen on a palladium - charcoal catalyst or with sodium borohydride yields ( ±)- nornicotine in moderate to good yields.

Properties

In nornicotine is a yellow liquid. It is a chiral compound which is composed of a pyridine and a pyrrolidine ring. Thus, there are two stereoisomers, (R)- nornicotine and (S) - nornicotine. By far the most important stereoisomer ( S)- nornicotine, which is often just called nornicotine. (S)- nornicotine has the same configuration as natural nicotine. (R ) - nornicotine and ( RS)- nornicotine [ synonym: rac- nornicotine ] have only minor importance.

Reactions

Nornicotine can be used for the synthesis of nicotine. The reaction can be carried out under the action of a base with methyl iodide or in a Leuckart -Wallach reaction with formaldehyde and formic acid.