Nereistoxin

Nereistoxin
Names
Preferred IUPAC name
N,N-Dimethyl-1,2-dithiolan-4-amine
Other names
NTX
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.121.136 Edit this at Wikidata
EC Number
  • Cartap: 239-309-2
KEGG
UNII
  • Nereistoxin: InChI=1S/C5H11NS2/c1-6(2)5-3-7-8-4-5/h5H,3-4H2,1-2H3
    Key: DSOOGBGKEWZRIH-UHFFFAOYSA-N
  • Cartap: InChI=1S/C7H15N3O2S2/c1-10(2)5(3-13-6(8)11)4-14-7(9)12/h5H,3-4H2,1-2H3,(H2,8,11)(H2,9,12)
    Key: IRUJZVNXZWPBMU-UHFFFAOYSA-N
  • Bensultap: Key: YFXPPSKYMBTNAV-UHFFFAOYSA-N
  • Nereistoxin: CN(C)C1CSSC1
  • Cartap: CN(C)C(CSC(=O)N)CSC(=O)N
Properties
C5H11NS2
Molar mass 149.27 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nereistoxin is a natural product identified in 1962 as the toxic organic compound N,N-dimethyl-1,2-dithiolan-4-amine. It had first been isolated in 1934 from the marine annelid Lumbriconereis heteropoda and acts by blocking the nicotinic acetylcholine receptor.[1] Researchers at Takeda in Japan investigated it as a possible insecticide. They subsequently developed a number of derivatives that were commercialised,[2][3] including those with the ISO common names[4] bensultap,[5] cartap,[6] thiocyclam[7] and thiosultap.[8][9]

  1. ^ Teuber, Lene (1990). "Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties". Sulfur Reports. 9 (4): 257–333. doi:10.1080/01961779008048732.
  2. ^ Roberts, Terry R; Hutson, David H, eds. (2007). "Nereistoxin precursors". Metabolic Pathways of Agrochemicals. pp. 127–138. doi:10.1039/9781847551375-00127. ISBN 978-0-85404-499-3.
  3. ^ Lewis, Kathleen A.; Tzilivakis, John; Warner, Douglas J.; Green, Andrew (2016). "An international database for pesticide risk assessments and management". Human and Ecological Risk Assessment. 22 (4): 1050–1064. Bibcode:2016HERA...22.1050L. doi:10.1080/10807039.2015.1133242. hdl:2299/17565. S2CID 87599872.
  4. ^ "Compendium of Pesticide Common Names". BCPC.
  5. ^ Pesticide Properties Database. "Bensultap". University of Hertfordshire.
  6. ^ Pesticide Properties Database. "Cartap". University of Hertfordshire.
  7. ^ Pesticide Properties Database. "Thiocyclam". University of Hertfordshire.
  8. ^ Pesticide Properties Database. "Thiosultap". University of Hertfordshire.
  9. ^ Konishi, Kazuo (1968). "New Insecticidally Active Derivatives of Nereistoxin". Agricultural and Biological Chemistry. 32 (5): 678–679. doi:10.1271/bbb1961.32.678.