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Corymine

From Wikipedia, the free encyclopedia
Chemical compound, neurotoxin

Corymine
Names
IUPAC name
Methyl (15E)-15-ethylidene-18-hydroxy-3-methyl-19-oxa-3,13-diazahexacyclo[14.3.1.02,10.02,13.04,9.010,17]icosa-4,6,8-triene-17-carboxylate
Other names
  • NSC381080
  • Corymin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • Key: KRTMWLRPHKYUJX-PQMHYQBVSA-N
  • InChI=1S/C22H26N2O4/c1-4-13-12-24-10-9-20-14-7-5-6-8-16(14)23(2)22(20,24)17-11-15(13)21(20,18(25)27-3)19(26)28-17/h4-8,15,17,19,26H,9-12H2,1-3H3/b13-4-
  • CC=C1CN2CCC34C2(C5CC1C3(C(O5)O)C(=O)OC)N(C6=CC=CC=C46)C
Properties
C22H26N2O4
Molar mass382.460 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Corymine, also known asNSC381080, is a naturalalkaloid found inHunteria zeylanica.

This compound acts as aglycine antagonist and could therefore, be classed as aneurotoxin.

Occurrence

[edit]

Corymine and many otherindole alkaloids can be isolated from parts of theHunteria zeylanica plant.

The plant also contains other similaralkaloids, such as[1]

  • 3-epi-dihydrocorymine
  • 3-epi-dihydrocorymine 3-acetate
  • 3-epi-dihydrocorymine 17-acetate
  • norisocorymine

Toxicity

[edit]

Corymine and related alkaloids can act asconvulsants.[2]

Tests onXenopus occyte species have shown that corymine can decreaseglycine's action at the inhibitoryglycine receptors.[3] These same tests have revealed that Corymine can reduce the response ofreceptors toGABA,[3] the primary inhibitory neurotransmitter.

Other experiments have shown that corymine can potentiate convulsions induced bystrychnine, a potentglycine antagonist.[4] This was also observed in mice.[5]

References

[edit]
  1. ^Lavaud C, Massiot G, Vercauteren J, Le Men-Olivier L (1982-01-01). "Alkaloids of Hunteria zeylanica".Phytochemistry.21 (2):445–447.Bibcode:1982PChem..21..445L.doi:10.1016/S0031-9422(00)95285-3.ISSN 0031-9422.
  2. ^"Corymine - Associated Disorders and Diseases".PubChem. U.S. National Library of Medicine. Retrieved2024-02-01.
  3. ^abLeewanich P, Tohda M, Matsumoto K, Subhadhirasakul S, Takayama H, Aimi N, et al. (August 1997). "Inhibitory effects of corymine, an alkaloidal component from the leaves of Hunteria zeylanica, on glycine receptors expressed in Xenopus oocytes".European Journal of Pharmacology.332 (3):321–326.doi:10.1016/s0014-2999(97)01097-2.PMID 9300267.
  4. ^Leewanich P, Tohda M, Matsumoto K, Subhadhirasakul S, Takayama H, Aimi N, et al. (May 1998). "A possible mechanism underlying corymine inhibition of glycine-induced Cl- current in Xenopus oocytes".European Journal of Pharmacology.348 (2–3):271–277.doi:10.1016/s0014-2999(98)00147-2.PMID 9652343.
  5. ^Leewanich P, Tohda M, Matsumoto K, Subhadhirasakul S, Takayama H, Aimi N, et al. (March 1996). "Behavioral studies on alkaloids extracted from the leaves of Hunteria zeylanica".Biological & Pharmaceutical Bulletin.19 (3):394–399.doi:10.1248/bpb.19.394.PMID 8924908.
Receptor
(ligands)
GlyRTooltip Glycine receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Transporter
(blockers)
GlyT1Tooltip Glycine transporter 1
GlyT2Tooltip Glycine transporter 2
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