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76-75-5 molecular structure
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5-ethyl-5-(pentan-2-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione

ChemBase ID: 481
Molecular Formular: C11H18N2O2S
Molecular Mass: 242.33782
Monoisotopic Mass: 242.10889883
SMILES and InChIs

SMILES:
S=C1NC(=O)C(C(CCC)C)(CC)C(=O)N1
Canonical SMILES:
CCCC(C1(CC)C(=O)NC(=S)NC1=O)C
InChI:
InChI=1S/C11H18N2O2S/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)
InChIKey:
IUJDSEJGGMCXSG-UHFFFAOYSA-N

Cite this record

CBID:481 http://www.chembase.cn/molecule-481.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-ethyl-5-(pentan-2-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione
IUPAC Traditional name
thiopental
Brand Name
Farmotal
Intraval
Nesdonal
Thiothal
Trapanal
Synonyms
Thiomebumal
Pentothiobarbital
Pentothal
Penthiobarbital
Thiopentone
Thiopentobarbituric acid
Thiopentobarbitone
Thiopentobarbital
Thionembutal
Tiopentale [Italian]
Thiopental
(±)Thiopental solution
5-Ethyldihydro-5-(1-methylbutyl)-2-thioxo-4,6(1H,5H)-pyrimidinedione
Intraval
5-Ethyl-5-(1-methylbutyl)-2-thiobarbituric acid
(±)-Thiopental
(±)戊硫代巴比妥 溶液
CAS Number
76-75-5
EC Number
200-659-6
200-984-3
MDL Number
MFCD00057564
PubChem SID
46504621
24899925
160963944
24899928
PubChem CID
3000715

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 7.2006354  H Acceptors
H Donor LogD (pH = 5.5) 2.7746518 
LogD (pH = 7.4) 2.3787088  Log P 2.7831209 
Molar Refractivity 65.9938 cm3 Polarizability 26.123722 Å3
Polar Surface Area 58.2 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.05  LOG S -3.78 
Solubility (Water) 3.98e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Acetone expand Show data source
Dichloromethane expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
Off-White Solid expand Show data source
Melting Point
158-160°C expand Show data source
Flash Point
11 °C expand Show data source
51.8 °F expand Show data source
Hydrophobicity(logP)
2.3 expand Show data source
Storage Condition
Controlled substance Refrigerator expand Show data source
RTECS
CQ6300000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Toxic Toxic (T) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
1230 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
3 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
11-23/24/25-39/23/24/25 expand Show data source
22 expand Show data source
Safety Statements
36/37/39 expand Show data source
7-16-36/37-45 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
Warning expand Show data source
GHS Hazard statements
H225-H301-H311-H331-H370 expand Show data source
H302 expand Show data source
GHS Precautionary statements
P210-P260-P280-P301 + P310-P311 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 1230 3/PG 2 expand Show data source
Drug Control
USDEA Schedule III; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98% expand Show data source
Concentration
1.0 mg/mL in methanol expand Show data source
1.0 mg/mL±5% in methanol expand Show data source
Grade
analytical standard, for drug analysis expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00599 external link
Item Information
Drug Groups approved
Description A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration. It is also used for hypnosis and for the control of convulsive states. It has been used in neurosurgical patients to reduce increased intracranial pressure. It does not produce any excitation but has poor analgesic and muscle relaxant properties. Small doses have been shown to be anti-analgesic and lower the pain threshold. (From Martindale, The Extra Pharmacopoeia, 30th ed, p920)
Indication For use as the sole anesthetic agent for brief (15 minute) procedures, for induction of anesthesia prior to administration of other anesthetic agents, to supplement regional anesthesia, to provide hypnosis during balanced anesthesia with other agents for analgesia or muscle relaxation, for the control of convulsive states during or following inhalation anesthesia or local anesthesia, in neurosurgical patients with increased intracranial pressure, and for narcoanalysis and narcosynthesis in psychiatric disorders.
Pharmacology Thiopental, a barbiturate, is used for the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli. Thiopental is an ultrashort-acting depressant of the central nervous system which induces hypnosis and anesthesia, but not analgesia. It produces hypnosis within 30 to 40 seconds of intravenous injection. Recovery after a small dose is rapid, with some somnolence and retrograde amnesia. Repeated intravenous doses lead to prolonged anesthesia because fatty tissues act as a reservoir; they accumulate Pentothal in concentrations 6 to 12 times greater than the plasma concentration, and then release the drug slowly to cause prolonged anesthesia
Toxicity Overdosage may occur from too rapid or repeated injections. Too rapid injection may be followed by an alarming fall in blood pressure even to shock levels. Apnea, occasional laryngospasm, coughing and other respiratory difficulties with excessive or too rapid injections may occur. Lethal blood levels may be as low as 1 mg/100 mL for short-acting barbiturates; less if other depressant drugs or alcohol are also present.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic. Biotransformation products of thiopental are pharmacologically inactive and mostly excreted in the urine.
Absorption Rapidly absorbed.
Half Life 3-8 hours
Protein Binding Approximately 80% of the drug in the blood is bound to plasma protein.
References
Morgan DJ, Blackman GL, Paull JD, Wolf LJ: Pharmacokinetics and plasma binding of thiopental. II: Studies at cesarean section. Anesthesiology. 1981 Jun;54(6):474-80. [Pubmed]
Perez-Barcena J, Barcelo B, Homar J, Abadal JM, Molina FJ, de la Pena A, Sahuquillo J, Ibanez J: [Comparison of the effectiveness of pentobarbital and thiopental in patients with refractory intracranial hypertension. Preliminary report of 20 patients] Neurocirugia (Astur). 2005 Feb;16(1):5-12; discussion 12-3. [Pubmed]
WINTERS WD, SPECTOR E, WALLACH DP, SHIDEMAN FE: Metabolism of thiopental-S35 and thiopental-2-C14 by a rat liver mince and identification of pentobarbital as a major metabolite. J Pharmacol Exp Ther. 1955 Jul;114(3):343-57. [Pubmed]
Bory C, Chantin C, Boulieu R, Cotte J, Berthier JC, Fraisse D, Bobenrieth MJ: [Use of thiopental in man. Determination of this drug and its metabolites in plasma and urine by liquid phase chromatography and mass spectrometry] C R Acad Sci III. 1986;303(1):7-12. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - T344800 external link
A thio-derivative of Barbituric acid. Controlled substance (depressant). Anesthetic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Bory C, Chantin C, Boulieu R, Cotte J, Berthier JC, Fraisse D, Bobenrieth MJ: [Use of thiopental in man. Determination of this drug and its metabolites in plasma and urine by liquid phase chromatography and mass spectrometry] C R Acad Sci III. 1986;303(1):7-12. Pubmed
  • • Morgan DJ, Blackman GL, Paull JD, Wolf LJ: Pharmacokinetics and plasma binding of thiopental. II: Studies at cesarean section. Anesthesiology. 1981 Jun;54(6):474-80. Pubmed
  • • Perez-Barcena J, Barcelo B, Homar J, Abadal JM, Molina FJ, de la Pena A, Sahuquillo J, Ibanez J: [Comparison of the effectiveness of pentobarbital and thiopental in patients with refractory intracranial hypertension. Preliminary report of 20 patients] Neurocirugia (Astur). 2005 Feb;16(1):5-12; discussion 12-3. Pubmed
  • • WINTERS WD, SPECTOR E, WALLACH DP, SHIDEMAN FE: Metabolism of thiopental-S35 and thiopental-2-C14 by a rat liver mince and identification of pentobarbital as a major metabolite. J Pharmacol Exp Ther. 1955 Jul;114(3):343-57. Pubmed
  • • Christensen, L., et al.: Toxicol. Appl. Pharmacol., 26, 495 (1973)
  • • McLeish, M. J., Anal. Profiles Drug Subs. Excip., 21, 535 (1973)
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PATENTS

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