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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is used in the treatment of ANXIETY DISORDERS, and also for the short-term management of INSOMNIA but has largely been superseded by the BENZODIAZEPINES.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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
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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 (meprobamate)
- 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
- NSC 30418
- 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
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-NSmiles
CCCC(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.