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solenopsin
Sign in to saveAlso known as solenopsin A, solenopsine A, (2R,6R)-2-methyl-6-undecylpiperidine
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.
Chemical data
- Formula
- C17H35N
- Molecular weight
- 253.5 g/mol
- IUPAC name
- (2R,6R)-2-methyl-6-undecylpiperidine
via PubChem
Wikidata facts
- Has part
- carbon
- Mass
- 253.27695011999998
Show 4 more facts
- chemical formula
- C₁₇H₃₅N
- canonical SMILES
- CCCCCCCCCCCC1CCCC(N1)C
- isomeric SMILES
- CCCCCCCCCCC[C@@H]1CCC[C@H](N1)C
- Commons category
- Solenopsin
via Wikidata · CC0
~4 min read
Encyclopedic overview
4 sectionsContents
- Total synthesis
- Biological activities
- References
- Further reading
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.
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.
Excerpted from Wikipedia’s “solenopsin” article, available under the CC BY-SA 4.0 licence.