Conhydrine

• ( )- α - Conhydrin
• (2S, 2 ' R) -2 - (2' -hydroxypropyl ) piperidine (IUPAC)
• Oxyconin

White crystals

Fixed

121 ° C.

224-226 ° C

0.4 mg · kg -1 ( LDLO, guinea pigs, s.c )

Template: Infobox chemical / molecular formula search available

Conhydrin is a Pseudoalkaloid, which was discovered in 1856 by Theodor Wertheim. It is a secondary amine, an α - substituted derivative of piperidine and contains an alcoholic hydroxyl group. In nature, it comes as ( )- Conhydrin in the spotted hemlock before ( Conium maculatum ), and is thus referred to in the literature as one of the Hemlock or Conium alkaloids.

Occurrence and biosynthesis

Conhydrin and its isomer Pseudoconhydrin occur almost exclusively in the spotted hemlock and mainly in the flowers. Conhydrin, Pseudoconhydrin and similar coniine and Methylconiin be synthesized in the plant by first tetramerized four C2 units to a 3,5,7 - Trioxo - octanoic acid, reduced and cyclized by a transamination of γ - coniceine. From the source material, the plant can manufacture any Conium alkaloids. A previously discussed biosynthetic pathway through lysine has now been disproved.

Toxicology

The toxicity of Conhydrin and Pseudoconhydrin are comparable. When symptoms appear spastic cramps and a drop in body temperature. The lowest known lethal dose is 400 micrograms per kg body weight in animal experiments. For humans Conhydrin and Pseudoconhydrin are less toxic than coniine. In the industrial production of coniine Conhydrin may arise as a byproduct.