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77-26-9 molecular structure
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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 and InChIs

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

Cite this record

CBID:126 http://www.chembase.cn/molecule-126.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-(2-methylpropyl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
IUPAC Traditional name
butalbital
Synonyms
Butalbital M (OH)
Allylbarbital
Butalbital
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
5-烯丙基-5-异丁基巴比妥酸
布他比妥
CAS Number
77-26-9
EC Number
201-017-8
MDL Number
MFCD00056089
Beilstein Number
202119
PubChem SID
46505876
24891925
160963589
PubChem CID
2481

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.481398  H Acceptors
H Donor LogD (pH = 5.5) 1.5888153 
LogD (pH = 7.4) 1.5550811  Log P 1.5892632 
Molar Refractivity 58.047 cm3 Polarizability 22.561075 Å3
Polar Surface Area 75.27 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.47  LOG S -2.0 
Solubility (Water) 2.23e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1700 mg/L expand Show data source
Hydrophobicity(logP)
1.7 expand Show data source
RTECS
CP8750000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-43 expand Show data source
Safety Statements
36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H317 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Drug Control
USDEA Schedule III; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00241 external link
Item Information
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 external link
Biochem/physiol Actions
镇静/催眠
Toronto Research Chemicals - B690100 external link
Controlled substance (depressant). Sedative, hypnotic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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