7206-76-0

Usage

Chemical Properties

White Crystalline Solid

Uses

A metabolite of Primidone

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Ethyl-2-phenylmalonamide is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Health Hazard

SYMPTOMS: Symptoms of exposure to a related compound through ingestion may include sedation, vertigo, dizziness, nausea, vomiting, ataxia, diplopia, nystagmus, an acute feeling of intoxication and, rarely, maculopapular and morbilliform rash, leukopenia, thrombocytopenia, systemic lupus erythematosus, lymphadenopathy, acute psychotic reactions, hemorrhagic disease in the neonate, megaloblastic anemia and osteomalacia.

Fire Hazard

Flash point data for 2-Ethyl-2-phenylmalonamide are not available. 2-Ethyl-2-phenylmalonamide is probably combustible.

InChI:InChI=1/C11H14N2O2.H2O/c1-2-11(9(12)14,10(13)15)8-6-4-3-5-7-8;/h3-7H,2H2,1H3,(H2,12,14)(H2,13,15);1H2

Upstream product

• 42282-82-6 3-ethyl-3-phenyl-azetidine-2,4-dione 
• 50-06-6 phenobarbital 
• 80544-75-8 (rac)-2-Cyan-2-phenylbutanamid 
• 76-67-5 diethyl ethyl(phenyl)malonate 
• 125-33-7 pirimidone 
• 75524-08-2 2-hydroxyprimidone 
• 24130-91-4 2-Aethyl-2-phenylmalonsaeuremonoamid 

Downstream Products

• 26739-88-8 2-ethyl-2-phenylmalononitrile 
• 125-33-7 pirimidone 
• 80278-08-6 5-ethyl-2-methoxy-5-phenyl-dihydro-pyrimidine-4,6-dione 
• 121429-24-1 2-(2,4-Diamino-1,3,5-triazin-6-yl)-2-phenylbarbituronitrile 
• 80544-75-8 (rac)-2-Cyan-2-phenylbutanamid 
• 58061-80-6 5-ethyl-5-(3-nitro-phenyl)-dihydro-pyrimidine-4,6-dione 
• 104396-69-2 5-ethyl-5-(3-amino-phenyl)-dihydro-pyrimidine-4,6-dione 

Relevant academic research and scientific papers

New chemical aspects of primidone metabolism

Primidone is metabolized either into phenylethylmalondiamide or phenobarbital. 2-Hydroxyprimidone was synthesized and tested as a potential intermediate common to these two biodegradation pathways in dogs as well as in vitro. On the other hand, the mechanism of the formation of α-phenyl-γ-butyrolactone during intoxication was investigated and the role of precursor played by the phenobarbital generated in vivo was shown.

Anticonvulsants in epileptic fowl

The high seizure susceptibility in epileptic fowl is an autosomal recessive trait characterized in homozygotes by seizures that occur spontaneously and in response to photic stimulation or hyperthermia. Both of the latter stimuli can be used to evoke seizures in drug studies. Epileptic fowl have abnormal inter-ictal EEG activity. When exposed to photic stimulation spiking is apparent on the EEG at seizure onset. Phenobarbital, primidone, phenytoin, and valproic acid reduce seizure susceptibility at plasma concentrations approximating those used to control generalized and focal cortical tonic-clonic seizures in humans. Carbamazepine and the benzodiazepines also reduce seizure susceptibility. These data include that epileptic fowl provide a useful model for generalized and focal cortical tonic-clonic epilepsies. Ethosuximide was inactive in epileptic fowl. However, trimethadione had anticonvulsant activity indicating that this model is only relatively specific for the above seizure types. When seizures were evoked by hyperthermia phenobarbital but not phenytoin or valproate reduced seizure susceptibility. GABA (γ-aminobutyric acid), AOAA (amino-oxyacetic acid) and THPO (4,5,6,7-tetrahydroisoxazolo[4,5-c] pyridin-3-ole, a glial specific inhibitor of GABA uptake) all have anticonvulsant activity against seizures evoked by photic stimulation in young chicks. These data indicate that this model may be particularly useful for studies of the anticonvulsant activity of compounds designed to enhance GABAergic transmission.