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

• ChemBase编号: 255
• 分子式: C9H18N2O4
• 平均质量: 218.25022
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-[(carbamoyloxy)methyl]-2-methylpentyl carbamate
• IUPAC传统名: sowell
• 商标名: 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
• 别名: 2-甲基-2-丙基-1,3-丙二醇二氨基甲酸酯; 甲丙氨酯; 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

登记号

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

理论计算性质

JChem

• Acid pKa: 15.171697
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 0.9272529
• LogD (pH = 7.4): 0.9272529
• Log P: 0.9272529
• 摩尔折射率: 53.0367 cm^3
• 极化性: 21.21696 Å^3
• 极化表面积: 104.64 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.06
• LOG S: -1.95
• 溶解度: 2.47e+00 g/l

分子性质

理化性质

• 溶解度: 4700 mg/L; Chloroform
• 外观: White Solid
• 熔点: 97-100°C
• 疏水性(logP): 0.7

安全信息

• 保存条件: Refrigerator
• RTECS编号: TZ0175000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 毒品管制信息: USDEA Schedule IV; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

产品相关信息

• 级别: analytical standard, for drug analysis

详细说明

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.

参考文献

• 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)