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

• ChemBase ID: 126
• Molecular Formular: C11H16N2O3
• Molecular Mass: 224.25634
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-methylpropyl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: butalbital
• Synonyms: 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; 5-烯丙基-5-异丁基巴比妥酸; 布他比妥

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.481398
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.5888153
• LogD (pH = 7.4): 1.5550811
• Log P: 1.5892632
• Molar Refractivity: 58.047 cm^3
• Polarizability: 22.561075 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.47
• LOG S: -2.0
• Solubility (Water): 2.23e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1700 mg/L
• Hydrophobicity(logP): 1.7

Safety Information

• RTECS: CP8750000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-43
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Drug Control: USDEA Schedule III; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

DETAILS

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.

REFERENCES

• 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)