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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
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
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
^ 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