Solenopsin is a lipophilicalkaloid 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]
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.
^Stereochemistry per: Leclercq S, Thirionet I, Broeders F, Daloze D, Vander Meer R, Braekman J (1994). "Absolute configuration of the solenopsins, venom alkaloids of the fire ants". Tetrahedron. 50 (28): 8465–8478. doi:10.1016/S0040-4020(01)85567-8.
^Gopalakrishnakone P, Calvete JJ (2021-01-14). Venom genomics and proteomics. Gopalakrishnakone, P.,, Calvete, Juan J. (Living Reference Work ed.). Dordrecht. ISBN9789400766495. OCLC968345667.{{cite book}}: CS1 maint: location missing publisher (link)
^Fox EG, Xu M, Wang L, Chen L, Lu YY (May 2018). "Speedy milking of fresh venom from aculeate hymenopterans". Toxicon. 146: 120–123. doi:10.1016/j.toxicon.2018.02.050. PMID29510162.