5-(2-methylpropyl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

• ChemBase编号: 126
• 分子式: C11H16N2O3
• 平均质量: 224.25634
• 单一同位素质量: 224.11609238
• SMILES: O=C1NC(=O)NC(=O)C1(CC(C)C)CC=C
• Canonical SMILES: C=CCC1(CC(C)C)C(=O)NC(=O)NC1=O
• InChI: InChI=1S/C11H16N2O3/c1-4-5-11(6-7(2)3)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16)
• InChIKey: UZVHFVZFNXBMQJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-(2-methylpropyl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
• IUPAC传统名: butalbital
• 别名: 5-烯丙基-5-异丁基巴比妥酸; 布他比妥; Butalbital; 5-(2-Methylpropyl)-5-(2-propen-1-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-Allyl-5-isobutylbarbituric Acid; 5-Allyl-5-(2-methylpropyl)barbituric Acid; 5-Allyl-5-(2'-methyl-n-propyl)barbituric Acid; Alisobumal; Allylbarbitone; Allylisobutylbarbital; Allylisobutylbarbituric acid; Butalbarbital; Fioricet; Isobutylallylbarbituric Acid; Isobutylallylbarturic Acid; Itobarbital; Sandoptal; Tetrallobarbital; Butalbital M (OH); Allylbarbital; Butalbital

登记号

• CAS号: 77-26-9
• EC号: 201-017-8
• MDL号: MFCD00056089
• Beilstein号: 202119
• PubChem SID: 160963589; 24891925; 46505876
• PubChem CID: 2481

理论计算性质

JChem

• Acid pKa: 8.481398
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 1.5888153
• LogD (pH = 7.4): 1.5550811
• Log P: 1.5892632
• 摩尔折射率: 58.047 cm^3
• 极化性: 22.561075 Å^3
• 极化表面积: 75.27 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.47
• LOG S: -2.0
• 溶解度: 2.23e+00 g/l

分子性质

理化性质

• 溶解度: 1700 mg/L
• 疏水性(logP): 1.7

安全信息

• RTECS编号: CP8750000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-43
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H317
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• 毒品管制信息: USDEA Schedule III; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

详细说明

DrugBank - DB00241

• Drug Groups: illicit; approved
• Description: Butalbital, 5-allyl-5-isobutylbarbituric acid, is a barbiturate with an intermediate duration of action. It has the same chemical formula as talbutal but a different structure. Butalbital is often combined with other medications, such as acetaminophen or aspirin, and is commonly prescribed for the treatment of pain and headache. [Wikipedia]
• Indication: Used in combination with acetaminophen or aspirin and caffeine for its sedative and relaxant effects in the treatment of tension headaches, migraines, and pain.
• Pharmacology: Butalbital is a short to intermediate-acting barbiturate. Barbiturates act as nonselective depressants of the central nervous system (CNS), capable of producing all levels of CNS mood alteration from excitation to mild sedation, hypnosis, and deep coma. In sufficiently high therapeutic doses, barbiturates induce anesthesia.
• Toxicity: Symptoms of acute barbiturate poisoning include drowsiness, confusion, coma, respiratory depression, hypotension, and shock.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, although most of the dose is eliminated via the kidney (59 to 88%). Urinary excretion products included parent drug (about 3.6% of the dose), 5-isobutyl-5-(2,3-dihydroxypropyl) barbituric acid (about 24% of the dose), 5-allyl-5(3-hydroxy-2-methyl-1-propyl) barbituric acid (about 4.8%).
• Absorption: Well absorbed from the gastrointestinal tract and is expected to distribute to most tissues in the body.
• Half Life: 35 hours
• Protein Binding: 45%
• External Links: Wikipedia; RxList

Sigma Aldrich - B6638

Biochem/physiol Actions
镇静/催眠

Toronto Research Chemicals - B690100

Controlled substance (depressant). Sedative, hypnotic.

参考文献

• Inaba, T., et al.: Clin. Pharmacol. Ther., 18, 558 (1975)
• Fritch, D., et al.: J. Anal. Toxicol., 33, 569 (1975)
• Wille, S., et al.: Ther. Drug Monit., 31, 511 (1975)