Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:27:14 UTC |
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Update Date | 2014-12-24 20:25:52 UTC |
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Accession Number | T3D2835 |
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Identification |
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Common Name | Thiopental |
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Class | Small Molecule |
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Description | Thiopental is 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) |
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Compound Type | - Amide
- Amine
- Anesthetic, Intravenous
- Anticonvulsant
- Drug
- GABA Modulator
- Hypnotic and Sedative
- Metabolite
- Organic Compound
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | (+-)-Thiopental | 2-Thio-5-ethyl-5-sec-pentylbarbituric acid | 5-Ethyl-5-(1-methyl-butyl)-2-thioxo-dihydro-pyrimidine-4,6-dione | Anestho | Bensulf | Bitaryl | Bitol Sodium | Ekipental | Farmotal | Intraval Sodium | Omexolon | Pental Sodyum | Pentazol | Penthal | Penthiobarbital | Penthotal Sodium | Pentotan | Pentotex | Pentothal | Pentothiobarbital | Ravonal | Sodium Pentothal | Thiomebumal | Thiomebumalum | Thionembutal | Thiopen | Thiopentobarbital | Thiopentobarbitone | Thiopentobarbituric acid | Thiopentone | Tiopental | Tiopentale | Trapanal |
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Chemical Formula | C11H18N2O2S |
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Average Molecular Mass | 242.338 g/mol |
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Monoisotopic Mass | 242.109 g/mol |
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CAS Registry Number | 76-75-5 |
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IUPAC Name | 5-ethyl-5-(pentan-2-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione |
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Traditional Name | thiopental |
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SMILES | CCCC(C)C1(CC)C(O)=NC(=S)N=C1O |
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InChI Identifier | InChI=1/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) |
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InChI Key | InChIKey=IUJDSEJGGMCXSG-UHFFFAOYNA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as thiobarbituric acid derivatives. These are organic compounds containing a 2-thioxodihydropyrimidine-4,6(1H,5H)-dione skeleton. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazines |
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Sub Class | Pyrimidines and pyrimidine derivatives |
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Direct Parent | Thiobarbituric acid derivatives |
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Alternative Parents | |
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Substituents | - Thiobarbiturate
- 1,3-diazinane
- Thiourea
- Azacycle
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | 3.98e-02 g/L | LogP | 2.85 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00bc-9240000000-1417d556dd6b075ba8eb | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0udi-0900000000-2256e1984e122af286e5 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0006-0090000000-c8a2b96397abdac51af0 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0006-4090000000-3397f51adf5ac5e26757 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-9010000000-2049e423160775847315 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-9000000000-e858eafc5134f3cf550e | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-9000000000-aed0d4351672086bb8bf | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-9000000000-aed0d4351672086bb8bf | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0006-0090000000-0da49458314b6213fc56 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0006-4090000000-5e98b0adc2fa68ac83f3 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-9000000000-35496d92c575e3289c20 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-9000000000-aed0d4351672086bb8bf | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-9000000000-e858eafc5134f3cf550e | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-9000000000-e858eafc5134f3cf550e | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0udi-0900000000-2f4595765496ded39eec | 2017-09-14 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-1290000000-56a5ebd429075bcf94ed | 2016-08-02 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01ox-1960000000-7b820ca9f1a89eb04af1 | 2016-08-02 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01bc-9100000000-fd47f0d49141ce724db7 | 2016-08-02 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0007-3980000000-015294919b010d958051 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9000000000-5046a8c65e5598a59005 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9200000000-b61e997b758e9e8e7bde | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0930000000-6c582f8c06229e7e804c | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-1930000000-f883235e554c70bfee48 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fs-4900000000-a6d44c5fa216c05bbc32 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0190000000-1e7490fbe84a7fcb8ef8 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052f-9000000000-ad244fddfe2755e5d199 | 2021-10-11 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0596-9600000000-1b2c7562818b87a3dce1 | 2014-09-20 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Parenteral (intravenous). Rapidly absorbed. |
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Mechanism of Toxicity | Thiopental binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. |
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Metabolism | Primarily hepatic. Biotransformation products of thiopental are pharmacologically inactive and mostly excreted in the urine.
Half Life: 3-8 hours |
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Toxicity Values | LD50: 50.6 mg kg −1(95% CI, 50.0–54.9) (i.v, mice) (5) |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | 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. Used commonly in the induction phase of general anesthesia. (Sodium-)thiopental is a depressant and is sometimes used during interrogations - not to cause pain (in fact, it may have just the opposite effect), but to weaken the resolve of the subject and make him or her more compliant to pressure. [Wikipedia] |
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Minimum Risk Level | Not Available |
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Health Effects | They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease. |
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Symptoms | 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. |
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Treatment | It is generally agreed that respiratory depression or arrest due to unusual sensitivity to thiopental sodium or overdosage is easily managed if there is no concomitant respiratory obstruction. If the airway is patent, any method of ventilating the lungs (that prevents hypoxia) should be successful in maintaining other vital functions. Since depression of respiratory activity is one of the characteristic actions of the drug, it is important to observe respiration closely. Should laryngeal spasm occur, it may be relieved by one of the usual methods, such as the use of a relaxant drug or positive pressure oxygen. Endotracheal intubation may be indicated in difficult cases. (7) |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00599 |
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HMDB ID | HMDB14737 |
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PubChem Compound ID | 3000715 |
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ChEMBL ID | CHEMBL441 |
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ChemSpider ID | 2272258 |
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KEGG ID | C07521 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 102166 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Thiopental |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Thiopental |
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References |
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Synthesis Reference | Not Available |
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MSDS | T3D2835.pdf |
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General 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. [7235275 ]
- 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. [15756405 ]
- 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. [13243246 ]
- 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. [3093002 ]
- Ben-Shlomo I, Rosenbaum A, Hadash O, Katz Y: Intravenous midazolam significantly enhances the lethal effect of thiopental but not that of ketamine in mice. Pharmacol Res. 2001 Dec;44(6):509-12. [11735358 ]
- Drugs.com [Link]
- RxList: The Internet Drug Index (2009). [Link]
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Gene Regulation |
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Up-Regulated Genes | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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Down-Regulated Genes | Not Available |
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