Anabaseine

Anabaseine
Chemical Structure of anabaseine
Names
Preferred IUPAC name
3,4,5,6-Tetrahydro-2,3′-bipyridine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C10H12N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8H,1-2,5,7H2 checkY
    Key: AUBPMADJYNSPOA-UHFFFAOYSA-N checkY
  • C1CCC(=NC1)c1cccnc1
Properties
C10H12N2
Molar mass 160.220 g·mol−1
Appearance Oil
Odor Odorless
Boiling point 110-120°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Anabaseine (3,4,5,6-tetrahydro-2,3′-bipyridine) is an alkaloid toxin produced by Nemertines worms and Aphaenogaster ants.[1] It is structurally similar to nicotine and anabasine.[2] Similarly, it has been shown to act as an agonist on most nicotinic acetylcholine receptors in the central nervous system and peripheral nervous system.[2]

  1. ^ Wheeler, JW; Olubajo, O; Storm, CB; Duffield, RM (6 March 1981). "Anabaseine: venom alkaloid of aphaenogaster ants". Science. 211 (4486): 1051–2. Bibcode:1981Sci...211.1051W. doi:10.1126/science.211.4486.1051. PMID 17744933.
  2. ^ a b Kem, William; Soti, Ferenc; Wildeboer, Kristin; LeFrancois, Susan; MacDougall, Kelly; Wei, Dong-Qing; Chou, Kuo-Chen; Arias, Hugo R. (2006-04-06). "The Nemertine Toxin Anabaseine and Its Derivative DMXBA (GTS-21): Chemical and Pharmacological Properties". Marine Drugs. 4 (3): 255–273. doi:10.3390/md403255. PMC 3663414.