619. Anabasine

Nomenclature

CAS number: 494-52-0
3-(2-Piperidinyl)pyridine; 2-(3-pyridyl)piperidine; neonicotine.
C10H14N2; mol wt 162.23.
C 74.04%, H 8.70%, N 17.27%.

Description and references

In Anabasis aphylla L., Chenopodiaceae: Orechoff, Menschikoff, Ber. 64, 266 (1931); in Nicotiana glauca Graham, Solanaceae: Smith, J. Am. Chem. Soc. 57, 959 (1935); Pyriki, Oehler, Pharmazie 9, 685 (1954). Synthesis: Spth, Ber. 70B, 70 (1937). Extracted on a large scale in Russia. Industrial extraction processes: Sadykov, Timbekov, J. Appl. Chem. USSR 29, 148 (1956). Abs config: Lukes et al., Collect. Czech. Chem. Commun. 27, 751 (1962).

Chemical structure

Properties

Liquid, bp 270-272°; bp14 145-147°; bp2 105°. Freezes at 9°. d420 1.0455. nD20 1.5430. [α]D20 83.1°. Sol in water and in most organic solvents.

Derivative

Hydrochloride.

Properties

[α]D +16.5° (c = 10 in water).

Caution

Acute and subacute toxicity: increased salivation, vertigo, confusion, disturbed vision and hearing, photophobia, cold extremities, nausea, vomiting, diarrhea, syncope, clonic spasms.

Use

Insecticide.