Anisatin

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Anisatin
Stereo skeletal formula of anisatin
Names
Preferred IUPAC name
(1R,4S,5R,6S,6aR,7R,9R,9aS)-1,5,6a,7-Tetrahydroxy-5,9-dimethylhexahydrospiro[[4,9a]methanocyclopenta[d]oxocine-6,3′-oxetane]-2,2′(1H)-dione
Identifiers
3D model (
JSmol
)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.208.646 Edit this at Wikidata
KEGG
MeSH Anisatin
UNII
  • InChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8-,9+,12+,13+,14+,15-/m1/s1 ☒N
    Key: GEVWHIDSUOMVRI-QWNPAUMXSA-N checkY
  • O=C1OC[C@]14[C@@]2(O)[C@H](O)C[C@H]([C@]23C[C@@H](OC(=O)[C@@H]3O)[C@@]4(O)C)C
Properties
C15H20O8
Molar mass 328.317 g·mol−1
log P -1.894
Acidity (pKa) 12.005
Basicity (pKb) 1.992
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Anisatin is an extremely

respiratory paralysis, which is the ultimate cause of death.[4]

Role in the GABA system

The

GABA system is an important site of action by a variety of chemicals, including alcohols, heavy metals, and insecticides.[5][6] A study conducted on frog spinal cords and rat brains indicated that anisatin was a strong non-competitive GABA antagonist.[5] Anisatin was shown to suppress GABA-induced signals, but when anisatin was added without GABA, there was no change in the signal.[5] Anisatin was also found to share the same binding site as picrotoxinin, and did not cause additional suppression of GABA-induced signals in the presence of high concentrations of picrotoxinin.[5]

Anisatin poisoning has been shown to cause epilepsy, hallucinations, nausea, and convulsions.[7][8] Diazepam has been studied as an anti-convulsive on the GABA system, and has been shown to be an effective treatment for anisatin-induced convulsions.[8]

Synthesis

A total synthesis of (-)-anisatin was reported in 1990.[9]

References

  1. ^ "Anisatin". PubChem, National Library of Medicine, US National Institutes of Health. 11 May 2019. Retrieved 17 May 2019.
  2. doi:10.1021/ja01133a002
    .
  3. doi:10.1039/P19880001537
    .
  4. ^ "Naoru.com:シキミ(Japanese)". Archived from the original on 2018-09-09. Retrieved 2009-03-11.
  5. ^
    PMID 10455311
    .
  6. PMID 28606041
    .
  7. PMID 26361344
    .
  8. ^
    PMID 22484123
    .
  9. ISSN 0002-7863
    .

External links

  • Media related to Anisatin at Wikimedia Commons
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