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HCID 8271Erstellt: 4. November 2026

Mephobarbital

METHYLPHENOBARBITAL · Metyna · Mebaral · Meberal · Mephytal · Morbusan · Phemiton · Prominal

https://huagongshe.com/de/chemical/8271

Molekülstruktur von Mephobarbital

Identifikatoren & physikalische Daten

CAS No.115-38-8
SummenformelC13H14N2O3
Durchschnittliche Molmasse246,26 g/mol
Monoisotopische Masse246,10044231 g/mol
SMILESCCC1(c2ccccc2)C(=O)NC(=O)N(C)C1=O
InChIKeyALARQZQTBTVLJV-UHFFFAOYSA-N
PubChem CID8271
ChEMBLCHEMBL45029
ChEBICHEBI:6758
EC No.204-085-7
DTXSIDDTXSID4023258

Chemische & physikalische Eigenschaften

XLogP1,8
Polarare Oberfläche (TPSA)66,5
H-Brücken-Donoren1
H-Brücken-Akzeptoren3
Frei drehbare Bindungen2
Schwere Atome18
Formalladung0
Komplexität388
ArzneimittelDEA NFLIS-Drug Category -> Depressants and TranquilizersDEA Schedule IV Controlled Substance -> DepressantsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive CompoundsPharmaceuticals -> Barbiturates
SpringerMaterials PropertiesCrystal structure
LogP (Verteilungskoeffizient)log Kow = 1.84
GeschmackTasteless
Color/FormWhite crystals from water
LöslichkeitSlightly solubleSlightly soluble in cold water, freely soluble in hot water or in alcohol.Slightly soluble in water, ethyl ether, chloroform, very soluble in ethanol7.10e-01 g/LPractically insoluble in water, very slightly soluble in ethanol (96 per cent).0.15g/L(20 ºC)
DecompositionWhen heated to decomposition it emits toxic /nitrogen oxide/.
Schmelzpunkt176 °C1760C
Physical DescriptionSolid
Stability/Shelf LifeMephobarbital tablets should be store in well-closed containers at a temperature less than 40 °C, preferably between 15-30 °C. Commercially available mephobarbital tablets have an expiration date of 5 years following the date of manufacture.
Dissociation Constants7.8
Siedepunkt389.26°C (rough estimate)
Dichte1.1855 (rough estimate)
Brechungsindex1.6450 (estimate)
Flammpunkt11 °C
LagerbedingungenControlled Substance, -20°C Freezer
pKa (Säurekonstante)7.99±0.10(Predicted)
AggregatzustandSolid
FarbeWhite to Off-White
CAS Datenbank115-38-8
EPA chemische Informationen2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl- (115-38-8)

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 4.5% (2 of 44) of reports.DangerH301 (88.6%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 44 reports by companies from 5 notifications to the ECHA C&L Inventory.
Regulatorische InformationenDEA schedule IV controlled substance
Weitere SicherheitsinformationenIMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-1-methyl-5-phenyl-: Human health tier I assessment
FDA-AnforderungenSchedule IV shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Each drug or substance has been assigned the DEA Controlled Substances Code Number set forth opposite it. Depressants. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation which contains any quantity of the following substances, including its salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation: Methylphenobarbital (DEA Code Number: 2250) is included on this list.
Hazard Classes and CategoriesAcute Tox. 3 (88.6%)
Skin, Eye, and Respiratory IrritationsMay cause irritation. Remove to fresh air. Flush with copious quantities of water.
BrandbekämpfungsverfahrenWater spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials.As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.
LagerbedingungenStore in tight container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.Store below 40 °C (104 °F), preferably between 15 and 30 °C (59 and 86 °F), unless otherwise specified by manufacturer. Store in a well-closed container. /Mephobarbital Tablets USP/

Anwendungen & Verwendung

Verwenden

Controlled substance (depressant). Anticonvulsant; sedative; hypnotic

ReinigungsverfahrenWipe up spillage or collect spillage using a high- efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.
EntsorgungsverfahrenSRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
Preventive MeasuresThis material is assumed to be combustible. As with all dry powders, it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling./Use/ safety glasses or goggles /and/ protect exposed skin.
Personal Protective Equipment (PPE)Engineering controls such as exhaust ventilation are recommended.Use a NIOSH-approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used.
WechselwirkungenPhenobarbital may decrease the half-life of doxycycline by inducing hepatic microsomal enzymes that metabolize the antibiotic. Concomitant administration of doxycycline and "barbiturates" should be avoided if possible. If concomitant therapy is necessary, doxycycline may be administered at 12-hour intervals and/or doxycycline concentrations should be closely monitored. /Barbiturates General Statement/Pretreatment with or concurrent administration of phenobarbital in patients receiving oral contraceptives may decrease the effectiveness of oral contraceptives. There have been reports of women receiving anticonvulsants (eg, phenobarbital) who became pregnant while receiving oral contraceptives. Phenobarbital may enhance the metabolism of both the estrogenic and progestinic components of oral contraceptives, presumably by induction of hepatic microsomal enzymes. Because of the risk of contraceptive failure during concomitant use of oral contraceptives and phenobarbital (or mephobarbital), it has been suggested that alternate methods of contraception be considered in patients receiving phenobarbital. /Barbiturates General Statement/"Barbiturates" may potentiate adverse effects (e.g., respiratory depression) induced by toxic doses of tricyclic antidepressants (e.g., amitriptyline, imipramine). With therapeutic doses of tricyclic antidepressants, "barbiturates" appear to stimulate metabolism and decrease blood concentrations of the antidepressantshowever, the clinical importance of this effect has not been established. /Barbiturates General Statement/"Barbiturates", especially phenobarbital, may decrease absorption of dicumarol from the GI tract. In addition, phenobarbital and possibly other "barbiturates" may induce hepatic microsomal enzymes resulting in increased metabolism of coumarin anticoagulants and decreased anticoagulant response. Patients maintained on both "barbiturates" and a coumarin anticoagulant have a risk of hemorrhage if the barbiturate is discontinued and the dosage of the anticoagulant is not adjusted. Barbiturate therapy should not be initiated or discontinued in patients receiving oral anticoagulants without careful attention to the possible need for adjusting anticoagulant dosage.For more Interactions (Complete) data for Methylphenobarbital (37 total), please visit the HSDB record page.
Milk ConcentrationsThe drugs are distributed into milk in concentrations much lower than those in plasma. /Barbiturates General Statement/
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Neonates born to women who receive barbiturates throughout the last trimester of pregnancy may show withdrawal symptoms from 1-14 days after birth. Withdrawal symptoms, which resemble congenital opiate withdrawal symptoms, include hyperactivity, restlessness, disturbed sleep, tremor, and hyperreflexia. /Barbiturates General Statement//SIGNS AND SYMPTOMS/ Symptoms of barbiturate dependence are similar to those of chronic alcoholism, but can be more severe than those associated with alcohol or opiate abstinence syndrome and may result in fatalities. Withdrawal symptoms (which usually appear after 8-12 hours of abstinence) may vary from mild, consisting only of weakness, anxiety, muscle twitches, insomnia, nausea, vomiting, postural hypotension, and/or weight loss, to more severe hallucinations, delirium, and seizures. Seizures, clinically indistinguishable from tonic-clonic (grand mal) seizures, may occur as early as 16 hours after the last dose of barbiturate or may be delayed for as long as 5 days. Some fatalities resulting from cardiovascular collapse have occurred. /Barbiturates General Statement//SIGNS AND SYMPTOMS/ Overdosage of barbiturates produces CNS depression ranging from sleep to profound coma to deathrespiratory depression which may progress to Cheyne-Stokes respiration, central hypoventilation, and cyanosiscold, clammy skin and/or hypothermia or later fever, areflexia, tachycardia, hypotension, loss of peripheral vascular resistance, muscular hyperactivity (twitching to convulsive-like movements) seizures, allergic reactions, and decreased urine formation. Pupils usually are slightly constricted but may be dilated in severe poisoning. Patients with severe overdosage often experience typical shock syndromeapnea, circulatory collapse with loss of peripheral vascular tone, cardiac arrest, respiratory arrest, and death may occur. Complications such as pneumonia, pulmonary edema, or renal failure may also prove fatal. Other complications which may occur are congestive heart failure, cardiac arrhythmias, and urinary tract infections. Some patients have bullous cutaneous lesions which heal slowly. Sweat gland necrosis may also occur. /Barbiturates General Statement//CASE REPORTS/ The authors report the case of a 32-year-old man who had been treated for anxiety and obsessive-compulsive disorder and had received 800 mg methylphenobarbital (MPB). After switching to a barbiturate-free schedule, his condition continued to be unstable for more than 21 MPB half-lives (approx. 30 days) and did not stabilize until MPB-metabolites dropped below their urinary detection limit. Considering that this article provides findings from a single patient, the authors use this experience to discuss and emphasize the importance of clinical control of barbiturates in psychiatry.For more Human Toxicity Excerpts (Complete) data for Methylphenobarbital (10 total), please visit the HSDB record page.
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)methylphenobarbitalDILI PositiveDOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ The authors examined the capability of N-substituted morpholinoalkyl derivated of phenobarbiral methylphenobarbital and glutetimide to induce drug-dissimilated enzymes in liver microsomes as those newly syntesized compounds were compared with the initial substances, which were enzyme inductors. They examined the following indices: duration of hexobarbital narcosis after a six day treatment of male white rats with one of the substances liver weight, related to the percentage of the whole body weight, protein content in liver homogenates and in microsomal fraction of liver, the activity of N-demetilase in liver. There was a considerable shortening of the duration of hexobarbital sleep due to barbiturates, more manifested in animals, treated with methylphenobarbital. Glutetimide shortened the /CNS depression/ statisticaly insignificant. The respective morpholonoalkylic derivatives not only did not shortened the /CNS depression/ sleep, but even slightly prolonged. it. The liver weight of the rats, treated with barbiturates, was increased with 25-30% while that of the rats treated with morpholinoalkylic derivatives did not differ from the liver weight of the control animals. The protein content in liver homogenates did not show statistically significant differences in the single groups. The protein content of the microsomal liver fraciton was increased in the animals, treated with barbiturates and glutetimide, while in the rats, treated with morphoalkylic derivatives the protein content did not differ from that of the controls, but it was even reduced after treatment with a derivative of glutetimide. Phenobarbital and methylphenobarbital increased significantly the activity of pyrimidone N-demetilase, while their N-substituted morpholinc-alkyli derivatives inhibited it./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The authors carried out histologic and electrone microscopic studies of liver in rats, treated with phenobarbital, methylphenobarbital, with their N-substituted morpholinoethye derivatives as well as in rats from the control group of animals. It was established that phenobarbital and methylphenobarbital caused hypertrophy and vacuolization of endoplasmatic reticulum, but the first preparation of the myelin degeneration of mitochindria as well. Morpholinethyl derivatives of the mentioned two compounds induced above all activation of lysosomes as well as reaction of Goldgi apparatus in the parenchymatous cells of liver. The observed ultrastructural changes were connected with differences in the induced drug-metabolizing enzymic properties of the two groups of compounds .../LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Phenobarbital sodium is carcinogenic in mice and rats following lifetime administrationin mice, the drug produced benign and malignant liver cell tumors and, in rats, benign liver cell tumors very late in life. /Barbiturates General Statement/
Populations at Special RiskGeriatric patients may react to usual doses of barbiturates with excitement, confusion, or depression. Many patients experience increased dreaming, nightmares, or increased insomnia when hypnotic doses of barbiturates are discontinued. /Barbiturates General Statement/Phenobarbital frequently produces paradoxical excitement and hyperactivity in children or exacerbates existing hyperactivity. Geriatric patients may react to usual doses of barbiturates with excitement, confusion, or depression, probably as a result of the drugs' depressant effects on inhibitory centers of the cerebral cortex. /Barbiturates General Statement/Barbiturates lower serum bilirubin concentrations in neonates and patients with congenital nonhemolytic unconjugated hyperbilirubinemia, presumably by induction of glucuronyl transferase, the enzyme that conjugates bilirubin. /Barbiturates General Statement//Investigators/ sequenced all nine exons and exon-intron junctions of the cytochrome P450 2C19 (CYP2C19) gene from a Japanese subject with a lowered capacity of CYP2C19-mediated 4'-hydroxylation after an oral administration of mephobarbital. /Investigators/ found a novel single nucleotide polymorphism (SNP) of CYP2C19 gene as follows: SNP, 040110MoritaJ001GENENAME: CYP2C19ACCESSION NUMBER: NT_030059.8LENGTH25 bases5'-GAGGGCCTGGCCC/TGCATGGAGCTGT-3'. The SNP (168946C>T) induced an amino acid alteration (Arg442Cys) located in exon 9 close to the heme-binding region of CYP2C19, which may result in the decrease in the catalytic properties of CYP2C19. A new allele having this SNP was designated as CYP2C19*16.
Probable Routes of Human ExposureNIOSH (NOES Survey 1981-1983) has statistically estimated that 340 workers (180 of these were female) were potentially exposed to methylphenobarbital in the US(1).
Antidote and Emergency TreatmentA 38-yr-old woman who by history ingested 13 g methylphenobarbital, alcohol, and 6 g acetaminophen became comatose slowly over 4 days. Acute hepatic injury appeared to impair the oxidative N-demethylation of methylphenobarbital to its product, phenobarbital. On the eighth day after ingestion she was treated because of protracted coma with Amberlite XAD-4 resin hemoperfusion. Hemoperfusion, which removed 0.83 g methylphenobarbital and 2.10 g phenobarbital, led to transient clinical improvement. When supportive patient management fails to produce a satisfactory clinical course in a methylphenobarbital-intoxicated patient, hemoperfusion could be a useful adjunct to therapy.Treatment of overdosage is mainly supportive including maintenance of an adequate airway and assisted respiration and oxygen administration if needed. Resuscitative measures should be initiated promptly. Standard treatment for shock should be administered if necessary. Management of hypotension may include administration of iv fluids, elevation of the lower extremities, and/or use of vasopressor or inotropic agents. For seizures, iv diazepam and phenytoin may be usedin case of refractory seizures, general anesthesia and paralysis induced by a neuromuscular blocking agent may be necessary. Activated charcoal is an effective barbiturate adsorbant when administered within 30 minutes following ingestion of the drugs. Gastric lavage or gastric aspiration is not recommended unless there is evidence that the drug has been ingested recently (within 4 hours)care should be taken to prevent pulmonary aspiration of gastric contents. Multiple-dose, nasogastric administration of activated charcoal has been used effectively to treat phenobarbital overdoseactivated charcoal enhances elimination of the drug and shortens the duration of coma. The patient's vital signs, fluid intake, blood gases, and serum electrolytes should be monitored closely. Analeptic drugs should not be administered because they may produce paroxysmal cerebral activity which may result in generalized seizures. In addition, it has been demonstrated that analeptics are incapable of stimulating respiration and exerting an arousal effect in patients with severe barbiturate poisoning and profound CNS depression. If renal function is normal, forced diuresis may be of benefit. In addition, alkalinization of the urine increases renal excretion of phenobarbital, aprobarbital, and mephobarbital which is metabolized to phenobarbital. Peritoneal dialysis or hemodialysis may be useful in severe barbiturate intoxication and/or if the patient is anuric or in shock. /Barbiturates General Statement/Orally administered activated charcoal has been shown to enhance the elimination of phenobarbital. Following iv administration of phenobarbital in healthy adults in one study, orally administered activated charcoal decreased the mean serum half-life of phenobarbital and increased mean total body and nonrenal clearances of the drug. /Barbiturates General Statement/For extravasation into subcutaneous tissues, recommended treatment includes application of moist heat to affected area and injection of a 0.5% procaine solution into the affected area. For accidental intra-arterial injection, recommended treatment includes release of tourniquet or restrictive garments to permit dilution of injected medicationinjection of 10 mL of a 1% procaine solution into the artery and, if necessary, brachial plexus block to relieve spasmanticoagulant therapy may prevent thrombosisand supportive treatment. /Barbiturates/For more Antidote and Emergency Treatment (Complete) data for Methylphenobarbital (10 total), please visit the HSDB record page.
Non-Human Toxicity ValuesLD50 Rat ip 130 mg/kgLD50 Mouse oral 300 mg/kgLD50 Cat oral 230 mg/kgLD50 Rabbit oral 400 mg/kg
UN-Transportnummer3249
Zollcode2933530000
R-Sätze (R)22-39/23/24/25-23/24/25-11
Toxizitätcat,LD50,oral,230mg/kg (230mg/kg),Drugs in Japan Vol. 6, Pg. 851, 1982.
GefahrensymboleXn,T,F
Sicherheitshinweise (S)36/37/39-45-36/37-16-7
Gefahrenklasse6.1(b)
VerpackungsgruppeIII
Gefahrstoffdaten115-38-8(Hazardous Substances Data)