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HCID 4064생성일: 2026년 11월 4일

메프로바메이트

메프로바메이트 · Diron · Mendel · Erina · Klort · Letyl · CaMHA · Oasil

https://huagongshe.com/ko/chemical/4064

메프로바메이트 분자 구조식

식별자 및 물리적 특성

CAS No.57-53-4
분자식C9H18N2O4
평균 분자량218.25 g/mol
단동위원소 질량218.12665706 g/mol
SMILESCCCC(C)(COC(N)=O)COC(N)=O
InChIKeyNPPQSCRMBWNHMW-UHFFFAOYSA-N
PubChem CID4064
ChEMBLCHEMBL979
ChEBICHEBI:6761
EC No.200-337-5
DTXSIDDTXSID3023261
현지명메프로바메이트

화학 및 물리적 성질

XLogP0.7
극성 표면적105
수소 결합 공여자 수2
수소 결합 수용자 수4
회전 가능 결합 수8
무거운 원자 수15
형식 전하0
복잡도212
물질 분류Pharmaceutical
의약품DEA NFLIS-Drug Category -> Depressants and TranquilizersDEA Schedule IV Controlled Substance -> DepressantsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> HypnoticsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
pHAqueous solutions are neutral
SpringerMaterials PropertiesFusion temperature
LogP(분배 계수)log Kow = 0.701.12
냄새Characteristic odor
맛Characteristic bitter taste
Color/FormCrystals from hot waterWhite powder
용해도less than 1 mg/mL at 68 °F (NTP, 1992)Very soluble in benzene, ethyl ether, ethanolEasily forms supersaturated solution with hot waterfreely soluble in most org solventsSolubility in water: 0.34% (w/w) at 20 °C0.79% at 37 °C (w/w)Slightly sol in ethersol in alcohol and acetone.DMF: 50 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 30 mg/mlEthanol: 25 mg/ml
Human DrugsBreast FeedingLactationMilk, HumanAnti-Anxiety AgentsHypnotics and SedativesMuscle Relaxants, CentralFDA approved drugs -> Active ingredient
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
DecompositionWhen heated to decomp it emits toxic fumes of /nitrogen oxides./
녹는점97-100°C
끓는 점358.93°C (rough estimate)
밀도1.2004 (rough estimate)
굴절률1.4480 (estimate)
인화점11 °C
저장 조건2-8°C
pKa(산도 계수)13.09±0.50(Predicted)
용해도6.2g/L(25℃)
헨리 상수5.5×104 mol/(m3Pa) at 25℃, HSDB (2015)
안정성안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다.
NIST1,3-Propanediol, 2-methyl-2-propyl-, dicarbamate(57-53-4)
EPAMeprobamate (57-53-4)

화학적 성질

white crystalline powder

안전 및 규제

GHS 분류WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 1 notifications to the ECHA C&L Inventory.
규제 정보Hazard Traits - Developmental ToxicityDEA schedule IV controlled substance1,3-Propanediol, 2-methyl-2-propyl-, dicarbamate: Does not have an individual approval but may be used under an appropriate group standard
기타 안전 정보IMAP assessments - 1,3-Propanediol, 2-methyl-2-propyl-, dicarbamate: Environment tier I assessment
화재 위험Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)
건강 유해성SYMPTOMS: Symptoms of exposure upon ingestion of this compound may include coma, blood pressure decrease, regional or general arteriolar constriction, dyspnea, cyanosis, respiratory depression, nausea, vomiting and allergic skin dermatitis. Other symptoms may include slight alterations of binocular vision and slight tendency to euphoria. Exposure to this compound may also cause drowsiness, diarrhea, paresthesia, weakness, headache, excitement, dizziness, ataxia, disturbances of vision, tachycardia, erythema multiform and, occasionally, skin rashes, angioneurotic edema, bronchospasm, anuria, agranulocytosis, eosinophilia, leucopenia and aplastic anemia. Other symptoms may include purpura, hypotension, cardiac arrhythmias and, occasionally, urticaria and thrombocytopenia. Exposure to this compound may result in acute intermittent porphyria, allergic or idiosyncratic reactions, slurred speech, vertigo, overstimulation, fast EEG activity, palpitations, arrhythmia, transient ECG changes, syncope, hypotensive crises, petechiae, ecchymoses, peripheral edema, adenopathy, fever, lethargy, stupor, shock, vasomotor and respiratory collapse, death, increased risk of congenital malformations and, rarely, hyperpyrexia, chills, oliguria, exfoliative dermatitis, anaphylaxis, stomatitis, proctitis, Stevens-Johnson syndrome and bullous dermatitis. Central nervous system depression may also occur. Other symptoms may include blood dyscrasias and hypothermia. Exposure to this compound also causes sleepiness, unsteadiness, mental confusion, slow and shallow respiration, flaccid muscles, hyperthermia, aspiration pneumonia, signs of lung consolidation, cerebral edema, laryngospasm, hangover emotional lability or depression, irritability, poor judgment, behavioral disturbances, vascular collapse, cardiac arrest and nonthrombocytopenic purpura. Other symptoms may include erythematous rash, angioedema, impaired stance and heart failure. In addition, areflexia, lack of response to sensory stimuli, excess oronasal secretions, relaxation of the pharyngeal wall muscular relaxation, pruritic eruptions, anaphylactoid reaction, fatal allergic collapse, fixed and unresponsive pupils, atelectasis and epileptiform seizures may occur.

용도

용도

An anxiolytic. This is a controlled substance.

일반 설명

Meprobamate,2-methyl-2-propyltrimethylene dicarbamate, 2-methyl-2-propyl-1,3-propanediol dicarbamate (Equanil, Miltown), is officiallyindicated as an antianxiety agent. It is also a sedative–hypnotic agent. It has several overall pharmacological properties resembling those of benzodiazepines and barbiturates.The mechanism of action underlying anxiolytic effectsis unknown but may involve effects on conductivity inspecific brain areas.It does not appear to act through effectson GABAergic systems.The drug is effective againstabsence seizures and may worsen generalized tonic–clonicseizures.

FDA 요건Schedule 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: Meprobamate (DEA Code Number: 2820) is included on this list.The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl meprobamate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
반응성 그룹Carbamates
Special ReportsCarson JMeprobamate revisited2 (2): 45-46 (1989). The history, clinical efficacy and adverse effects of meprobamate, a nonbenzodiazepine anxiolytic agent, are discussed. Meprobamate is found to have questionable efficacy and be more dangerous in overdose than benzodiazepines. Although potential for abuse is hard to quantify, it appears that meprobamate has equivalent, if not greater, potential for abuse when compared with benzodiazepines. It is concluded that an increase in meprobamate use would not be in the best interest of patients.
Reactivity ProfileMEPROBAMATE is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
소화Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
응급 처치EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital.
보관 조건Meprobamate preparations generally should be stored in tight containers at a temperature less than 40 °C, preferably at 15-30 °C. However, USP states that the tablets can be stored in well-closed containers. The fixed-combination tablets of meprobamate and aspirin should be stored in tight, light-resistant containers at 20-25 °C and protected from moisture.
비화재 누출 대응SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
처리 방법SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Personal Protective Equipment (PPE)RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
체내 부담Meprobamate crosses the placentathe maternal blood meprobamate levels approximate those of the fetus. Meprobamate is excreted in breast milk and should not be given to lactating mothers. An epidemiologic study of the use of meprobamate in pregnancy (1,870 offspring) did not reveal any increased evidence of fetal demise or abnormalities when these children were studied until 4 years of age.Meprobamate is distributed into the milk of lactating women in a concentration 2-4 times that in plasma.
상호 작용Excretion of meprobamate may be incr to point of net tubular secretion by addn of furosemide to saline diuresis. This resulted in excretion of 35% of admin dose of meprobamate over 4 hr period.Although animal studies indicated that meprobamate shortened the half-life of warfarin, subsequent human studies have shown the meprobamate does not have any clinically important effect on warfarin-induced hypoprothrombinemia.Although imipramine enhances the CNS effects of meprobamate in animals, no clinically important effect of this interaction has been documented in humans.Additive CNS depression may occur when meprobamate is administered concomitantly with other CNS depressants, including alcohol. If meprobamate is used concomitantly with other depressant drugs, including alcohol, caution should be used to avoid overdosage.For more Interactions (Complete) data for MEPROBAMATE (6 total), please visit the HSDB record page.
HepatotoxicityRates of serum enzyme elevations during meprobamate therapy have not been reported. While instances of clinically apparent liver injury due to meprobamate have been mentioned in review articles, no cases with specific information on clinical features have appeared in the published literature. Thus, meprobamate may be capable of causing clinically apparent liver injury, but it must be rare. Meprobamate is metabolized in the liver via the cytochrome P450 system and has major potential for drug-drug interactions. Meprobamate can exacerbate symptoms of porphyria. Serious allergic reactions to meprobamate have been reported including Stevens Johnson syndrome. In cases of meprobamate overdose, the cause of death has been respiratory suppression and not liver failure, although liver histology was not well defined.
환경 거동TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a log Kow of 0.70(2) and a regression-derived equation(3), indicates that meprobamate is expected to have high mobility in soil(SRC). Volatilization of meprobamate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Meprobamate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Meprobamate has been classified as non-biodegradable(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a log Kow of 0.70(2) and a regression-derived equation(3), indicates that meprobamate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.8X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Meprobamate has been classified as non-biodegradable(7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), meprobamate, which has an estimated vapor pressure of 3.0X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase meprobamate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 20 hours(SRC), calculated from its rate constant of 1.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Meprobamate does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Milk ConcentrationsEXPERIMENTAL: Meprobamate is excreted in /human/ breast milk and should not be given to lactating mothers.EXPERIMENTAL: Meprobamate is distributed into the milk of lactating women in a concentration 2-4 times that in plasma.
Soil Adsorption/MobilityThe Koc of meprobamate is estimated as 60(SRC), using a log Kow of 0.70(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that meprobamate is expected to have high mobility in soil.
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Sudden withdrawal of the drug after prolonged and excessive use may precipitate recurrence of pre-existing symptoms such as anxiety, anorexia, insomnia, or withdrawal reactions such as vomiting, ataxia, tremors, muscle twitching, confusional states, hallucinosis, and rarely, convulsive seizures. Such seizures are more likely to occur in persons with central nervous system damage or pre-existent or latent convulsive disorders. Onset of withdrawal symptoms occurs usually within 12 to 48 hours after discontinuation of meprobamatesymptoms usually cease within the next 12 to 48 hours./SIGNS AND SYMPTOMS/ Physical dependence, psychological dependence, and abuse have occurred. When chronic intoxication from prolonged use occurs, it usually involves ingestion of greater than recommended doses and is manifested by ataxia, slurred speech, and vertigo. Therefore, careful supervision of dose and amounts prescribed is advised, as well as avoidance of prolonged administration, especially for alcoholics and other patients with a known propensity for taking excessive quantities of drugs./SIGNS AND SYMPTOMS/ Tolerance and psychologic and physical dependence may occur following prolonged use of high doses of meprobamate. Daily ingestion of 3.2 g of meprobamate for weeks or months has produced physical dependence and withdrawal symptoms when the drug was suddenly discontinued. Because of the drug's potential for inducing dependence, prolonged administration of meprobamate is not recommended./SIGNS AND SYMPTOMS/ Symptoms of meprobamate dependence are similar to those of barbiturate dependence or chronic alcoholism and may include drowsiness, ataxia, slurred speech, and vertigo. Sudden discontinuance of the drug in physically dependent patients may produce severe withdrawal symptoms within 12-48 hours including anxiety, anorexia, insomnia, vomiting, ataxia, tremors, muscle twitching, confusion, hallucinations, and seizures clinically indistinguishable from generalized tonic-clinic (grand mal) seizures. Seizures are most likely to occur in patients ingesting large amounts of the drug or patients who have CNS damage or a history of seizure disorders. Some fatalities have occurred following abrupt withdrawal of meprobamate. Withdrawal symptoms usually cease within 12-48 hours they appear.For more Human Toxicity Excerpts (Complete) data for MEPROBAMATE (18 total), please visit the HSDB record page.
Artificial Pollution SourcesMeprobamate's production and use as an antianxiety agent(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationAEROBIC: Meprobamate has been classified as non-biodegradable(1).
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)MeprobamatevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015
Environmental BioconcentrationAn estimated BCF of 3 was calculated in fish for meprobamate(SRC), using a log Kow of 0.70(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/SoilThe Henry's Law constant for meprobamate is estimated as 1.8X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that meprobamate is expected to be essentially nonvolatile from water surfaces(2). Meprobamate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-3 mm Hg(SRC), determined from a fragment constant method(3).
수질 위해 등급(WGK)3
TSCA 등재 상태TSCA listed
RTECS 번호TZ0175000
운송 번호(UN)UN 1230 3/PG 2
독성LD50 i.p. in mice: 800 mg/kg (Berger)
관세 코드2924110000
위험 문구(R)22-39/23/24/25-23/24/25-11
위험 표시Xn,T,F
안전 문구(S)7-16-36/37-45
유해 물질 데이터57-53-4(Hazardous Substances Data)