82111-06-6

Usage

Uses

Used in Pest Control Industry:
5-METHYLNICOTINE is used as an insecticide for controlling and eliminating various types of insects. As a nicotine analog, it effectively targets and disrupts the nervous systems of insects, leading to their paralysis and eventual death. This makes it a valuable tool in agriculture and other industries where insect control is crucial for protecting crops and maintaining a healthy ecosystem.

Upstream product

• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 29681-45-6 5-methylnicotinic acid methyl ester 
• 1253523-00-0 tert-butyl 2-(5-methylpyridin-3-yl)pyrrolidine-1-carboxylate 
• 42885-14-3 5-cyano-3-methylpyridine 
• 50-00-0 formaldehyd 
• 102780-52-9 5-methylmyosmine 

Relevant academic research and scientific papers

One-pot formation of piperidine- and pyrrolidine-substituted pyridinium salts via addition of 5-alkylaminopenta-2,4-dienals to N-acyliminium ions: Application to the synthesis of (±)-nicotine and analogs

Addition of 5-alkylaminopenta-2,4-dienals onto N-acyliminium ions, generated in situ from α-hydroxycarbamates derived from pyrrolidine or piperidine, in the presence of zinc triflate, followed by dehydrative cyclization, allowed the formation of pyridinium salts substituted at their 3-position by a five- or six-membered nitrogen heterocycle. Subsequent N-dealkylation of the pyridinium moiety and deprotection of the secondary amine or reduction of the carbamate function led to (±)-nicotine and analogs.

Determination of Nicotine N-Oxide by Gas Chromatography following Thermal Conversion to 2-Methyl-6-(3-pyridyl)tetrahydro-1,2-oxazine

Nicotine N-oxide is extracted from urine by use of silica gel columns and eluted with methanolic ammonia.The eluate is evaporated and then heated at 150-160 deg C in anisole, which results in conversion to the ring-expansion product 2-methyl-6-(3-pyridyl)tetrahydro-1,2-oxazine.The oxazine derivative is readily extracted from aqueous solution with organic solvents and has good chromatographic properties.A method for determination of nicotine N-oxide in smoker's urine, using 5-methylnicotine N-oxide as an internal standard, is described.

Steric and Conformational Effects in Nicotine Chemistry

The stereoselectivity of iodomethylation of nicotine and seven nicotine analogues having pyridine alkyl groups was determined by using 13C NMR.Alkylation at the pyridine (N) and at the pyrrolidine (N') nitrogens was observed.Two modes of N'-iodomethylation occur, cis and trans to the pyridine ring.N'-Iodomethylation occurs regioselectively cis to the pyridine ring for all compounds examined.The N/N' and N'cis/N'trans ratios for the nicotinoids were evaluated with regard to (1) the orientation of the N'-methyl group in the free base, (2) conformational properties of the pyridine ring with respect to the pyrrolidine ring, and (3) steric hindrance and buttressing effects on the pyridine nitrogen.The Curtin-Hammett principle and the Winstein-Holness equation are used to analyse reactions.