Solenopsin
Chemical compound / From Wikipedia, the free encyclopedia
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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[2] and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings.[3]
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Preferred IUPAC name
(2R,6R)-2-Methyl-6-undecylpiperidine[1] | |
Other names
Solenopsin A | |
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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).
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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.[4] Fire ant venom contains other chemically related piperidines which make purification of solenopsin from ants difficult.[5][6] 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,[7] several groups have designed novel and creative methods of synthesizing enantiopure solenopsin and other alkaloidal components of ant venom.