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Substance Name: Meprobamate [USP:INN:BAN:JAN]
RN: 57-53-4
UNII: 9I7LNY769Q
InChIKey: NPPQSCRMBWNHMW-UHFFFAOYSA-N

Note

  • A carbamate with hypnotic, sedative, and some muscle relaxant properties, although in therapeutic doses reduction of anxiety rather than a direct effect may be responsible for muscle relaxation. Meprobamate has been reported to have anticonvulsant actions against petit mal seizures, but not against grand mal seizures (which may be exacerbated). It is used in the treatment of ANXIETY DISORDERS, and also for the short-term management of INSOMNIA but has largely been superseded by the BENZODIAZEPINES. (From Martindale, The Extra Pharmacopoeia, 30th ed, p603)

Molecular Formula

  • C9-H18-N2-O4

Molecular Weight

  • 218.2512
 

Classification Codes

Classification Codes

  • Anti-Anxiety Agents
  • Anticonvulsants
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Hypnotics and Sedatives
  • Muscle Relaxants, Central
  • Mutation Data
  • Neuromuscular Agents
  • Peripheral Nervous System Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Sedative-Hypnotic
  • Tranquilizing Agents

Superlist Classification Code

  • DEA Schedule IV

Names and Synonyms

Name of Substance

  • Meprobamate
  • Meprobamate [USP:INN:BAN:JAN]

MeSH Heading

  • Meprobamate

Synonyms

  • 2,2-Di(carbamoyloxymethyl)pentane
  • 2-Methyl-2-n-propyl-1,3-propanediol dicarbamate
  • 2-Methyl-2-propyl-1,3-propanediol dicarbamate
  • 2-Methyl-2-propyltrimethylene carbamate
  • 2-Metil-2-n-propil-1,3-propanediol dicarbamato
  • 2-Metil-2-n-propil-1,3-propanediol dicarbamato [Spanish]
  • 3P Bamate
  • 4-03-00-00073 (Beilstein Handbook Reference)
  • Amepromat
  • Amosene
  • Anastress
  • Anathylmon
  • Anatimon
  • Andaksin
  • Andaxin
  • Aneural
  • Ansiatan
  • Ansil
  • Ansiowas
  • Anural
  • Anxietil
  • Anzil
  • Apascil
  • Appetrol-Sr
  • Arcoban
  • Arpon
  • Artolon
  • Atraxin
  • Auxietil
  • Ayeramate
  • Bamate
  • Bamo 400
  • Biobamat
  • Biobamate
  • BRN 1788882
  • Calmadin
  • Calmax
  • Calmiren
  • Canquil-400
  • Cap-O-Tran
  • Carbamic acid, 2-methyl-2-propyltrimethylene ester
  • Carbaxin
  • Cirpon
  • Cirponyl
  • Crestanil
  • Cyrpon
  • Dapaz
  • Deprol
  • Despasmol
  • Dicandiol
  • Diron
  • Diurnal
  • Diurnaldiverondormabrol
  • Diveron
  • Dormabrol
  • Ecuanil
  • Edenal
  • EINECS 200-337-5
  • Enorden
  • Epicur
  • Epikur
  • Equanil
  • Equanil suspension
  • Equatrate
  • Equazine-M
  • Equilium
  • Equitar
  • Erina
  • Estasil
  • Fas-Cile 200
  • Gadexyl
  • Harmonin
  • Hartol
  • Holbamate
  • HSDB 3117
  • Ipsotian
  • Kesso-Bamate
  • Klort
  • Larten
  • Lepenil
  • Lepetown
  • Letyl
  • Libiolan
  • Mar-Bate
  • Margonil
  • Mendel
  • Mepantin
  • Mepavlon
  • Mepiosine
  • Meposed
  • Mepranil
  • Mepriam
  • Meprin
  • Meprin (VAN)
  • Meprindon
  • Mepro-analgesic
  • Meprobam
  • Meprobamat
  • Meprobamat [German]
  • Meprobamate
  • Meprobamate and Aspirin Tablets
  • Meprobamato
  • Meprobamato [INN-Spanish]
  • Meprobamato [Italian]
  • Meprobamatum
  • Meprobamatum [INN-Latin]
  • Meproban
  • Meprocompren
  • Meprocon
  • Meprocon CMC
  • Meprodil
  • Meprodiol
  • Meprol
  • Meproleaf
  • Meprosa
  • Meprosan
  • Meprosin
  • Meprospan
  • Meprospan-200
  • Meprospan-400
  • Meprotabs
  • Meprotan
  • Meprotanum
  • Meprotil
  • Meprovanmeprozine
  • Meptran
  • Meptranactylmilprem
  • Metractyl
  • Metranquil
  • Micrainin
  • Milpath
  • Milprem
  • Milprem-400
  • Miltamato
  • Miltaun
  • Miltown
  • Miltown 600
  • Neuramate
  • Tranmep
  • UNII-9I7LNY769Q

Systematic Names

  • 1,3-Propanediol, 2-methyl-2-propyl-, 1,3-dicarbamate
  • 1,3-Propanediol, 2-methyl-2-propyl-, dicarbamate
  • Meprobamate

Superlist Names

  • DEA No. 2820
  • Meprobamate

Mixture Names

  • Appetrol
  • Deprol
  • Equagesic
  • Micrainin
  • Milpath
  • Milprem
  • Miltrate
  • Pathibamate
  • PMB-200
  • PMB-400

Registry Numbers

CAS Registry Number

  • 57-53-4

FDA UNII

  • 9I7LNY769Q

System Generated Number

  • 0000057534

Structure Descriptors

InChI

1S/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13)

InChIKey

NPPQSCRMBWNHMW-UHFFFAOYSA-N

Smiles

C(COC(=O)N)(COC(=O)N)(CCC)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 80mg/kg (80mg/kg) BEHAVIORAL: COMA Human Toxicology. Vol. 4, Pg. 215, 1985.
guinea pig LD50 subcutaneous 380mg/kg (380mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 375, 1962.
hamster LD50 intraperitoneal 625mg/kg (625mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
hamster LD50 oral 1410mg/kg (1410mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
human TDLo oral 280mg/kg (280mg/kg) BEHAVIORAL: COMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Ohio State Medical Journal. Vol. 52, Pg. 1304, 1956.
man LDLo unreported 441mg/kg (441mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo oral 5700ug/kg (5.7mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: NAUSEA OR VOMITING

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
Journal of the Irish Medical Association. Vol. 41, Pg. 119, 1957.
man TDLo oral 114mg/kg (114mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

BEHAVIORAL: COMA
Clinical Toxicology. Vol. 11, Pg. 501, 1977.
mouse LD50 intraperitoneal 331mg/kg (331mg/kg)   Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 23, Pg. 281, 1971.
mouse LD50 intravenous 230mg/kg (230mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 12, Pg. 447, 1977.
mouse LD50 oral 750mg/kg (750mg/kg)   Journal of Medicinal Chemistry. Vol. 15, Pg. 998, 1972.
mouse LD50 subcutaneous 520mg/kg (520mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 26, Pg. 109, 1974.
rabbit LD50 intravenous 260mg/kg (260mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: REGIDITY

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
International Journal of Neuropharmacology. Vol. 5, Pg. 305, 1966.
rat LD50 intraperitoneal 410mg/kg (410mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
rat LD50 intravenous 350mg/kg (350mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Prensa Medica Argentina. Vol. 44, Pg. 915, 1957.
rat LD50 oral 794mg/kg (794mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 93, 1971.
rat LD50 subcutaneous 525mg/kg (525mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 56, Pg. 377, 1960.
women LDLo oral 760mg/kg (760mg/kg) BEHAVIORAL: COMA JAMA, Journal of the American Medical Association. Vol. 207, Pg. 361, 1969.
women TDLo oral 112mg/kg (112mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: COMA
Clinical Toxicology. Vol. 11, Pg. 501, 1977.
women TDLo oral 120mg/kg (120mg/kg) BEHAVIORAL: COMA

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Clinical Toxicology. Vol. 11, Pg. 501, 1977.
women TDLo oral 240mg/kg (240mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA
Clinical Toxicology. Vol. 11, Pg. 501, 1977.
women TDLo oral 360mg/kg (360mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: COMA
Clinical Toxicology. Vol. 11, Pg. 501, 1977.
women TDLo oral 384mg/kg (384mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

VASCULAR: REGIONAL OR GENERAL ARTERIOLAR CONSTRICTION
Northwest Medicine. Vol. 56, Pg. 321, 1957.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 105 deg C   EXP
log P (octanol-water) 0.7 (none)   EXP
Water Solubility 4700 mg/L 25 EXP
Vapor Pressure 3.05E-03 mm Hg 25 EST
Henry's Law Constant 1.85E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.93E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.