Coriamyrtin
Convulsant toxin
Coriamyrtin[ 1]
Names
IUPAC name
(1S ,2R ,3S ,5R ,6R ,7R ,9S ,12R )-2-Hydroxy-7-methyl-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one
Other names
Coriamyrtine
Identifiers
InChI=1S/C15H18O5/c1-6(2)8-7-4-13(3)14(5-18-14)10-11(20-10)15(13,17)9(8)12(16)19-7/h7-11,17H,1,4-5H2,2-3H3/t7-,8+,9+,10+,11-,13-,14+,15-/m0/s1
Key: BWWDLKVKPVKBGJ-TWMZOSGRSA-N
CC(=C)C1C2CC3(C4(CO4)C5C(C3(C1C(=O)O2)O)O5)C
Properties
C 15 H 18 O 5
Molar mass
278.304 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
Coriamyrtin is a toxic γ-lactone naturally present in a multitude of plants.
Natural occurrence
Coriamyrtin can be found in Scurrula parasitica ,[ 2] Coriaria microphylla ,[ 3] and certain other plants.
Toxicity
Coriamyrtin is a convulsant .[ 4] It appears to act via antagonism of GABAA receptors .[ 5] Poisoning is usually from ingestion of parts of the plants containing it. A case of poisoning was able to be treated with repeated administration of diazepam , an anticonvulsant .[ 6]
References
^ "Coriamyrtin" .
^ PubChem. "Scurrula parasitica" . pubchem.ncbi.nlm.nih.gov . Retrieved 2024-02-11 .
^ PubChem. "Coriaria microphylla" . pubchem.ncbi.nlm.nih.gov . Retrieved 2024-02-11 .
^ "T3DB: Coriamyrtin" . www.t3db.ca . Retrieved 2024-02-11 .
^ Pérez, Claudia; Becerra, José; Manríquez-Navarro, Paula; Aguayo, Luis Gerardo; Fuentealba, Jorge; Guzmán, José Leonardo; Joseph-Nathan, Pedro; Jiménez, Verónica; Muñoz, Marcelo Andrés; Silva, Mario (2011). "Inhibitory activities on mammalian central nervous system receptors and computational studies of three sesquiterpene lactones from Coriaria ruscifolia subsp. ruscifolia" . Chemical & Pharmaceutical Bulletin . 59 (2): 161–165. doi :10.1248/cpb.59.161 . ISSN 1347-5223 . PMID 21297293 .
^ de Haro, Luc; Pommier, Philip; Tichadou, Lucia; Hayek-Lanthois, Maryvonne; Arditti, Jocelyne (November 2005). "Poisoning by Coriaria myrtifolia Linnaeus: a new case report and review of the literature" . Toxicon . 46 (6): 600–603. Bibcode :2005Txcn...46..600D . doi :10.1016/j.toxicon.2005.06.026 . ISSN 0041-0101 . PMID 16165183 .
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see here for a full list): α-EMTBL
Alcohols (e.g., drinking alcohol , 2M2B )
Anabolic steroids
Avermectins (e.g., ivermectin )
Barbiturates (e.g., phenobarbital )
Benzodiazepines (e.g., diazepam )
Bromide compounds (e.g., potassium bromide )
Carbamates (e.g., meprobamate )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g., ergoloid (dihydroergotoxine) )
Etazepine
Etifoxine
Fenamates (e.g., mefenamic acid )
Flavonoids (e.g., apigenin , hispidulin )
Fluoxetine
Flupirtine
Imidazoles (e.g., etomidate )
Kava constituents (e.g., kavain )
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g., allopregnanolone , cholesterol , THDOC )
Niacin
Niacinamide
Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil ), cyclopyrrolones (e.g., zopiclone ), imidazopyridines (e.g., zolpidem ), pyrazolopyrimidines (e.g., zaleplon ))
Norfluoxetine
Petrichloral
Phenols (e.g., propofol )
Phenytoin
Piperidinediones (e.g., glutethimide )
Propanidid
Pyrazolopyridines (e.g., etazolate )
Quinazolinones (e.g., methaqualone )
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g., baicalin )
Stiripentol
Sulfonylalkanes (e.g., sulfonmethane (sulfonal) )
Topiramate
Valerian constituents (e.g., valerenic acid )
Volatiles /gases (e.g., chloral hydrate , chloroform , diethyl ether , paraldehyde , sevoflurane )
Negative modulators: 1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α3IA
α5IA (LS-193,268)
β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids
Amiloride
Anisatin
β-Lactams (e.g., penicillins , cephalosporins , carbapenems )
Basmisanil
Bemegride
Bicyclic phosphates (TBPS , TBPO , IPTBO )
BIDN
Bilobalide
Bupropion
CHEB
Chlorophenylsilatrane
Cicutoxin
Cloflubicyne
Cyclothiazide
DHEA
DHEA-S
Dieldrin
(+)-DMBB
DMCM
DMPC
EBOB
Etbicyphat
FG-7142 (ZK-31906)
Fiproles (e.g., fipronil )
Flavonoids (e.g., amentoflavone , oroxylin A )
Flumazenil
Fluoroquinolones (e.g., ciprofloxacin )
Flurothyl
Furosemide
Golexanolone
Iomazenil (123 I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g., apalutamide , bicalutamide , enzalutamide , flutamide , nilutamide )
Oenanthotoxin
Pentylenetetrazol (pentetrazol)
Phenylsilatrane
Picrotoxin (i.e., picrotin , picrotoxinin and dihydropicrotoxinin )
Pregnenolone sulfate
Propybicyphat
PWZ-029
Radequinil
Ro 15-4513
Ro 19-4603
RO4882224
RO4938581
Sarmazenil
SCS
Suritozole
TB-21007
TBOB
TBPS
TCS-1105
Terbequinil
TETS
Thujone
U-93631
Zinc
ZK-93426
GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor