Corymine

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 mass 382.460 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Corymine, also known as NSC381080, is a natural alkaloid found in Hunteria zeylanica.

This compound acts as a glycine antagonist and could therefore, be classed as a neurotoxin.

Occurrence

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Corymine and many other indole alkaloids can be isolated from parts of the Hunteria zeylanica plant.

The plant also contains other similar alkaloids, such as[1]

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

Toxicity

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Corymine and related alkaloids can act as convulsants.[2]

Tests on Xenopus occyte species have shown that corymine can decrease glycine's action at the inhibitory glycine receptors.[3] These same tests have revealed that Corymine can reduce the response of receptors to GABA,[3] the primary inhibitory neurotransmitter.

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

References

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  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. Retrieved 2024-02-01.
  3. ^ a b Leewanich 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.
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