Solenopsin

Solenopsin is a lipophilic alkaloid with the molecular formula C17H35N found in the venom of fire ants (Solenopsis). It is considered the primary toxin in the venom and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings.

Solenopsin
Names
Preferred IUPAC name
(2R,6R)-2-Methyl-6-undecylpiperidine
Other names
Solenopsin A
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C17H35N/c1-3-4-5-6-7-8-9-10-11-14-17-15-12-13-16(2)18-17/h16-18H,3-15H2,1-2H3/t16-,17-/m1/s1 Y
    Key: AYJGABFBAYKWDX-IAGOWNOFSA-N Y
  • CCCCCCCCCCC[C@@H]1CCC[C@H](N1)C
Properties
C17H35N
Molar mass 253.474 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Structurally solenopsins are a piperidine ring with a methyl group substitution at position 2 and a long hydrophobic chain at position 6. They are typically oily at room temperature, water-insoluble, and present an absorbance peak at 232 nanometers. Fire ant venom contains other chemically related piperidines which make purification of solenopsin from ants difficult. Therefore, solenopsin and related compounds have been the target of organic synthesis from which pure compounds can be produced for individual study. Originally synthesized in 1993, several groups have designed novel and creative methods of synthesizing enantiopure solenopsin and other alkaloidal components of ant venom.

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