ContaminantDB: Trimethadione

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:40 UTC

Update Date

2026-05-14 16:36:07 UTC

Accession Number

CHEM002179

Identification

Common Name

Trimethadione

Class

Small Molecule

Description

Trimethadione is only found in individuals that have used or taken this drug. It is an anticonvulsant effective in absence seizures, but generally reserved for refractory cases because of its toxicity. (From AMA Drug Evaluations Annual, 1994, p378) Trimethadione reduces T-type calcium currents in thalamic neurons, including thalamic relay neurons. It does so via the inhibition of voltage dependent T-type calcium channels. This raises the threshold for repetitive activity in the thalamus, and inhibits corticothalamic transmission. Thus, the abnormal thalamocortical rhythmicity, which is thought to underlie the 3-Hz spike-and-wave discharge seen on electroencephalogram(EEG) with absence seizures, is dampened.

Contaminant Sources

HMDB Contaminants - Urine
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anticonvulsant
Drug
Ester
Ether
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Tridione	Kegg
Trimetadione	HMDB
Trimethadion	HMDB
Trimethdione	HMDB
Abbott brand OF trimethadione	HMDB
Trimetin	HMDB
Troxidone	HMDB

Chemical Formula

C₆H₉NO₃

Average Molecular Mass

143.141 g/mol

Monoisotopic Mass

143.058 g/mol

CAS Registry Number

127-48-0

IUPAC Name

trimethyl-1,3-oxazolidine-2,4-dione

Traditional Name

trimethadione

SMILES

CN1C(=O)OC(C)(C)C1=O

InChI Identifier

InChI=1S/C6H9NO3/c1-6(2)4(8)7(3)5(9)10-6/h1-3H3

InChI Key

IRYJRGCIQBGHIV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as oxazolidinediones. Oxazolidinediones are compounds containing an oxazolidine ring which bears two ketones.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Oxazolidines

Direct Parent

Oxazolidinediones

Alternative Parents

Substituents

Oxazolidinedione
Dicarboximide
Carbamic acid ester
Carbonic acid derivative
Oxacycle
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	46°C
Boiling Point	Not Available
Solubility	5E+004 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	212 g/L	ALOGPS
logP	0.07	ALOGPS
logP	0.5	ChemAxon
logS	0.17	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.2 m³·mol⁻¹	ChemAxon
Polarizability	13.59 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-8900000000-43db0866b0f6797cbff6	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0006-1900000000-5560efcfc7260e1dcfef	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-8900000000-43db0866b0f6797cbff6	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0006-1900000000-5560efcfc7260e1dcfef	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9100000000-88bba4b2f392389bb2d0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1900000000-cadbfe428b3321b1cc08	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-5ed5d9dd884dba589024	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9000000000-d3d40f4617407850f4a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-2900000000-0d39e71814a5ed15503f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-6900000000-690c1be64c11bb697283	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-79613f1372991c39908a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-bf6efd173e2ec81ec24b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0005-9100000000-7199f0f2792c2c7abbf3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-e010af24e65b7370041d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-4900000000-3e2daa1ffb23c9cf8e6c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-54c03842913d8ee3d521	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-0173eb4fd0e871a137e0	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9200000000-46082deb9c636fb8f625	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Dione anticonvulsants reduce T-type calcium currents in thalamic neurons, including thalamic relay neurons. It does so via the inhibition of voltage dependent T-type calcium channels. This raises the threshold for repetitive activity in the thalamus, and inhibits corticothalamic transmission. Thus, the abnormal thalamocortical rhythmicity, which is thought to underlie the 3-Hz spike-and-wave discharge seen on electroencephalogram(EEG) with absence seizures, is dampened.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used in the control of absence (petit mal) seizures that are refractory to treatment with other medications.

Minimum Risk Level

Not Available

Health Effects

May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Symptoms of overdose include clumsiness or unsteadiness, coma, dizziness (severe), drowsiness (severe), nausea (severe), and problems with vision.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00347

HMDB ID

HMDB0014491

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Trimethadione (CHEM002179)

Structure for CHEM002179: Trimethadione