Coriamyrtin

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
3D model (JSmol)	Interactive image;
PubChem CID	442189;
CompTox Dashboard (EPA)	DTXSID50948589 ;
	InChI 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;
	SMILES CC(=C)C1C2CC3(C4(CO4)C5C(C3(C1C(=O)O2)O)O5)C;
Properties
Chemical formula	C15H18O5
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). Infobox references

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 GABA_A 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.

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[1] "Coriamyrtin".

[2] PubChem. "Scurrula parasitica". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-02-11.

[3] PubChem. "Coriaria microphylla". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-02-11.

[4] "T3DB: Coriamyrtin". www.t3db.ca. Retrieved 2024-02-11.

[5] 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.

[6] 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.

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v t e Convulsants
GABA receptor antagonists	Bicuculline Bicyclic phosphates (TBPS, TBPO, IPTBO) BIDN Chlorophenylsilatrane Cicutoxin Cloflubicyne Coriamyrtin Dihydropicrotoxinin DMCM EBOB Endosulfan FG-7142 Fipronil Flurothyl Gabazine Oenanthotoxin Pentylenetetrazol Phenylsilatrane Picrotoxin p-CN-TBOB p-NCS-TBOB RDX TBOB Tetramethylenedisulfotetramine Thujone Trimethylolpropane phosphite Tutin
GABA synthesis inhibitors	3-Mercaptopropionic acid 4-Deoxypyridoxine Allylglycine Crimidine Decaborane Ginkgotoxin Isoniazid Pentaborane Thiocarbohydrazide Toxopyrimidine
Glycine receptor antagonists	Coriamyrtin Dendrobine Picrotoxin Strychnine Tutin
Glutamate receptor agonists	AMPA Domoic acid Kainic acid NMDA Quisqualic acid Tetrazolylglycine
Convulsant barbiturates	CHEB Diberal (DMBB) McN-481
Other	2,2,3,3-Tetrafluoropropyl trifluoromethyl ether Bromocamphor Camphor FAZ-4 Fluoroethyl fluoroacetate MC-2973 Methionine sulfoximine Methyl fluoroacetate Nitrocyclohexane Thebaine

v t e Neurotoxins
Animal toxins	Batrachotoxin Bestoxin Birtoxin Bungarotoxin Charybdotoxin Conotoxin Fasciculin Huwentoxin Poneratoxin Saxitoxin Tetrodotoxin Vanillotoxin Spooky toxin (SsTx) Epibatidine Zetekitoxin AB Dendrotoxin
Bacterial	Botulinum toxin Tetanospasmin
Cyanotoxins	Anatoxin-a Guanitoxin BMAA Saxitoxin
Plant toxins	Aconitine Bicuculline Penitrem A Picrotoxin Strychnine Tutin Rotenone Ginkgotoxin Cicutoxin Oenanthotoxin Thujone Volkensin Veratridine
Mycotoxins	Ibotenic acid Muscarine Muscimol
Pesticides	Fenpropathrin Tetramethylenedisulfotetramine Bromethalin Crimidine Methamidophos Endosulfan Fipronil Phenylsilatrane Chlorophenylsilatrane Sulfuryl fluoride Mipafox Schradan Dimefox
Nerve agents	Cyclosarin EA-3148 Novichok agent Sarin Soman Tabun VE VG VM VP VR VX GV EA-3990 EA-4056 T-1123 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) Fluorotabun Chinese VX EA-2192
Bicyclic phosphates	TBPS TBPO IPTBO
Cholinergic neurotoxins	Acetylcholine mustard Catecholine Choline mustard Ethylcholine mustard Hemicholinium mustard
Psychoactive drugs	Alcohol Nitrous oxide
Other	Dimethylcadmium Dimethylmercury Toxopyrimidine IDPN Tetraethyllead

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
3D model (JSmol)	Interactive image
PubChem CID	442189
CompTox Dashboard (EPA)	DTXSID50948589
InChI 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
SMILES CC(=C)C1C2CC3(C4(CO4)C5C(C3(C1C(=O)O2)O)O5)C
Properties
Chemical formula	C₁₅H₁₈O₅
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). Infobox references