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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
Identifiers
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
C 22 H 26 N 2 O 4
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).
Chemical compound
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 [ edit ]
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 [ edit ]
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 [ edit ]
^ 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 .
^ PubChem. "Corymine - Associated Disorders and Diseases" . pubchem.ncbi.nlm.nih.gov . Retrieved 2024-02-01 .
^ a b Leewanich, P.; Tohda, M.; Matsumoto, K.; Subhadhirasakul, S.; Takayama, H.; Aimi, N.; Watanabe, H. (1997-08-13). "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 . ISSN 0014-2999 . PMID 9300267 .
^ Leewanich, P.; Tohda, M.; Matsumoto, K.; Subhadhirasakul, S.; Takayama, H.; Aimi, N.; Watanabe, H. (1998-05-08). "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 . ISSN 0014-2999 . PMID 9652343 .
^ Leewanich, P.; Tohda, M.; Matsumoto, K.; Subhadhirasakul, S.; Takayama, H.; Aimi, N.; Watanabe, H. (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 . ISSN 0918-6158 . PMID 8924908 .
Receptor (ligands )
GlyR Tooltip Glycine receptor
Positive modulators: Alcohols (e.g., brometone , chlorobutanol (chloretone) , ethanol (alcohol) , tert -butanol (2M2P) , tribromoethanol , trichloroethanol , trifluoroethanol )
Alkylbenzene sulfonate
Anandamide
Barbiturates (e.g., pentobarbital , sodium thiopental )
Chlormethiazole
D12-116
Dihydropyridines (e.g., nicardipine )
Etomidate
Ginseng constituents (e.g., ginsenosides (e.g., ginsenoside-Rf ))
Glutamic acid (glutamate)
Ivermectin
Ketamine
Neuroactive steroids (e.g., alfaxolone , pregnenolone (eltanolone) , pregnenolone acetate , minaxolone , ORG-20599 )
Nitrous oxide
Penicillin G
Propofol
Tamoxifen
Tetrahydrocannabinol
Triclofos
Tropeines (e.g., atropine , bemesetron , cocaine , LY-278584 , tropisetron , zatosetron )
Volatiles /gases (e.g., chloral hydrate , chloroform , desflurane , diethyl ether (ether) , enflurane , halothane , isoflurane , methoxyflurane , sevoflurane , toluene , trichloroethane (methyl chloroform) , trichloroethylene )
Xenon
Zinc
Antagonists: 2-Aminostrychnine
2-Nitrostrychnine
4-Phenyl-4-formyl-N-methylpiperidine
αEMBTL
Bicuculline
Brucine
Cacotheline
Caffeine
Colchicine
Colubrine
Cyanotriphenylborate
Dendrobine
Diaboline
Endocannabinoids (e.g., 2-AG , anandamide (AEA) )
Gaboxadol (THIP)
Gelsemine
iso-THAZ
Isobutyric acid
Isonipecotic acid
Isostrychnine
Laudanosine
N-Methylbicuculline
N-Methylstrychnine
N,N-Dimethylmuscimol
Nipecotic acid
Pitrazepin
Pseudostrychnine
Quinolines (e.g., 4-hydroxyquinoline , 4-hydroxyquinoline-3-carboxylic acid , 5,7-CIQA , 7-CIQ , 7-TFQ , 7-TFQA )
RU-5135
Sinomenine
Strychnine
Thiocolchicoside
Tutin
Negative modulators: Amiloride
Benzodiazepines (e.g., bromazepam , clonazepam , diazepam , flunitrazepam , flurazepam )
Corymine
Cyanotriphenylborate
Daidzein
Dihydropyridines (e.g., nicardipine , nifedipine , nitrendipine )
Furosemide
Genistein
Ginkgo constituents (e.g., bilobalide , ginkgolides (e.g., ginkgolide A , ginkgolide B , ginkgolide C , ginkgolide J , ginkgolide M ))
Imipramine
NBQX
Neuroactive steroids (e.g., 3α-androsterone sulfate , 3β-androsterone sulfate , deoxycorticosterone , DHEA sulfate , pregnenolone sulfate , progesterone )
Opioids (e.g., codeine , dextromethorphan , dextrorphan , levomethadone , levorphanol , morphine , oripavine , pethidine , thebaine )
Picrotoxin (i.e., picrotin and picrotoxinin )
PMBA
Riluzole
Tropeines (e.g., bemesetron , LY-278584 , tropisetron , zatosetron )
Verapamil
Zinc
NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2