2-[(carbamoyloxy)methyl]-2-methylpentyl carbamate

• ChemBase ID: 255
• Molecular Formular: C9H18N2O4
• Molecular Mass: 218.25022
• Monoisotopic Mass: 218.12665707
• SMILES: O(CC(CCC)(COC(=O)N)C)C(=O)N
• Canonical SMILES: CCCC(COC(=O)N)(COC(=O)N)C
• 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-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(carbamoyloxy)methyl]-2-methylpentyl carbamate
• IUPAC Traditional name: sowell
• Brand Name: 3P bamate; Amepromat; Amosene; Anastress; Anathylmon; Anatimon; Andaksin; Andaxin; Aneural; Aneurol; Aneusral; Aneuxal; Aneuxral; Ansiatan; Ansietan; Ansil; Ansiowas; Anural; Anxietil; Anzil; Apascil; Apasil; Apo-Meprobamate; Appetrol; Appetrol-Sr; Arcoban; Arpon; Artolon; Ataraxine; Atraxin; Auxietil; Ayeramate; Ayermate; Bamate; Bamd 400; Bamo 400; Biobamat; Biobamate; Brobamate; Calmadin; Calmax; Calmiren; Canquil 400; Canquil-400; Carbaxin; Cirpon; Cirponyl; Coprobate; Crestanil; Cypron; Cyrpon; Dapaz; Deprol; Despasmol; Dicandiol; Diron; Diurnal; Diveron; Dormabrol; Ecuanil; Edenal; Enorden; Epicur; Epikur; Equagesic; Equanil; Equatrate; Equazine-M; Equilium; Equinil; Equitar; Erina; Estasil; Fas-Cile; Fas-Cile 200; Gadexyl; Gagexyl; Harmonin; Hartol; Holbamate; Ipsotian; Kesso-Bamate; Kessobamate; Klort; Larten; Lepenil; Lepetown; Letyl; Libiolan; Madiol; Mar-Bate; Margonil; Mendel; Mepamtin; Mepantin; Mepavlon; Mepiosine; Meposed; Mepranil; Mepriam; Meprin; Meprindon; Mepro-Aspirin; Mepro-analgesic; Meprobam; Meprobamat; Meproban; Meprocompren; Meprocon; Meprocon CMC; Meprodil; Meprodiol; Meprol; Meproleaf; Mepron; Mepronil; Meprosa; Meprosan; Meprosin; Meprospan; Meprotabs; Meprotan; Meprotanum; Meproten; Meprotil; Meprovan; Meprozine; Meptran; Mesmar; Metractyl; Metranquil; Micrainin; Milpath; Milprem; Miltamato; Miltann; Miltaun; Miltown; Miltrate; Miltuan; Miltwon; Misedant; Morbam; Multaun; My-trans; Neo-Tran; Nephentine; Nervonus; Neuramate; Oasil; Optarket; Orlevol; Orolevol; Pan-tranquil; Pancalma; Panediol; Pankalma; Pathibamate; Paxin; Pensive; Perequietil; Perequil; Perquietil; Pertranquil; Pimal; Placidon; Placitate; Prequil; Probamato; Probamyl; Probate; Procalmadiol; Procalmadol; Procalmidol; Promate; Promato; Proquanil; Protran; Q-Gesic; Quaname; Quanane; Quanil; Quietidon; Quivet; Rastenil; Reostral; Restenil; Restenyl; Restinal; Restinil; Restran; Robamate; SK-Bamate; Sadanyl; Scolazil; Sedabamate; Sedanil; Sedanyl; Sedazil; Sedoquil; Sedoselecta; Selene; Seril; Setran; Shalvaton; Solevione anastress; Sowell; Spantran; Stensolo; Tamate; Tensol; Tensonal; Trancot; Trankvilan; Tranlisant; Tranmep; Tranquil; Tranquilan; Tranquilate; Tranquilax; Tranquiline; Tranquillin; Tranquilsan; Tranquinol; Tranquisan; Trelmar; Urbil; Urbilat; Vio-Bamate; Vistabamate; Wardamate; Wyseals; Zirpon
• Synonyms: Bamo 400; Biobamat; Quaname; 2-Methyl-2-propyl-1,3-propanediol Dicarbamate; NSC 30418; Pertranquil; Placidon; Placitate; Probamyl; Procalmadiol; Procalmidol; Promate; Protran-d3; Amosene-d3; Anastress; Anatimon; Andaxin; Aneural; Ansiatan; Anzil; Apascil; Appetrol; Arcoban; Artolon Atraxin; Ayeramate; MPB; Meprobamate; Meprobamat [German]; Meprobamatum [INN-Latin]; Meprobamato [Italian]; Meprobamato [INN-Spanish]; Meprobamic acid; DEA No. 2820; Procarbamide; Meprobamate; 2-甲基-2-丙基-1,3-丙二醇二氨基甲酸酯; 甲丙氨酯

Database IDs

• CAS Number: 57-53-4
• EC Number: 200-337-5
• MDL Number: MFCD00063428
• PubChem SID: 160963718; 46508142; 24896728
• PubChem CID: 4064

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.171697
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.9272529
• LogD (pH = 7.4): 0.9272529
• Log P: 0.9272529
• Molar Refractivity: 53.0367 cm^3
• Polarizability: 21.21696 Å^3
• Polar Surface Area: 104.64 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.06
• LOG S: -1.95
• Solubility (Water): 2.47e+00 g/l

PROPERTIES

Physical Property

• Solubility: 4700 mg/L; Chloroform
• Apperance: White Solid
• Melting Point: 97-100°C
• Hydrophobicity(logP): 0.7

Safety Information

• Storage Condition: Refrigerator
• RTECS: TZ0175000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule IV; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Product Information

• Grade: analytical standard, for drug analysis

DETAILS

DrugBank - DB00371

• Drug Groups: illicit; approved
• Description: 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) Meprobamate is a controlled substance in the U.S.
• Indication: For the management of anxiety disorders or for the short-term relief of the symptoms of anxiety.
• Pharmacology: Meprobamate is an anxiolytic drug. It was the best selling minor tranquilizer for a time but has largely been replaced by benzodiazepines. Meprobamate has most of the pharmacological effects and dangers of the barbiturates (though it was marketed as being safer). However, it is less sedating at effective doses. It is reported to have some anticonvulsant properties against absence seizures, but can exacerbate generalized tonic-clonic seizures. It has also been used as a hypnotic (sleeping pill). However, its is currently only licensed as an anxiolytic and it is a third or fourth-order choice.
• Toxicity: Symptoms of overdose include coma, drowsiness, loss of muscle control, severely impaired breathing, shock, sluggishness, and unresponsiveness. Death has been reported with ingestion of as little as 12 g meprobamate and survival with as much as 40 g.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Well absorbed from the gastrointestinal tract.
• Half Life: Plasma half-life is about 10 hours.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - M2392

Biochem/physiol Actions
通过增加 Cl- 流来增强 GABAA 受体活性。高浓度时，阻断 NMDA 谷氨酸受体电。

Toronto Research Chemicals - M227750

An anxiolytic.This is a controlled substance.

REFERENCES

• Summerfield, S., et al.: J. Pharmacol. Exp. Ther., 322, 205 (2007)
• Ma, C., et al.: J. Pharm. Biomed. Anal., 47, 677 (2007)
• Cone, E., et al.: J. Anal. Toxicol., 33, 1 (2007)