5-(pentan-2-yl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione

• ChemBase ID: 1025
• Molecular Formular: C12H18N2O2S
• Molecular Mass: 254.34852
• Monoisotopic Mass: 254.10889883
• SMILES: S=C1NC(=O)C(C(CCC)C)(CC=C)C(=O)N1
• Canonical SMILES: CCCC(C1(CC=C)C(=O)NC(=S)NC1=O)C
• InChI: InChI=1S/C12H18N2O2S/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)
• InChIKey: XLOMZPUITCYLMJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(pentan-2-yl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione
• IUPAC Traditional name: thioseconal; thiamylal
• Brand Name: Surital; Thioseconal
• Synonyms: Thiamylal; Thiamylal; Thiamylal; Thioseconal; Surital; Dihydro-5-(1-methylbutyl)-5-(2-propen-1-yl)-2-thioxo-4,6(1H,5H)-pyrimidinedione; Dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-4,6(1H,5H)-pyrimidinedione; 5-Allyl-5-(1-methylbutyl)-2-thiobarbituric acid; Bio-Tal; NSC 120815; 5-烯丙基-5-(1-甲基丁基)-2-硫代巴比妥酸; 硫戊巴比妥

Database IDs

• CAS Number: 77-27-0
• EC Number: 201-018-3
• MDL Number: MFCD00057565
• PubChem SID: 160964488; 24900605; 46506261
• PubChem CID: 3032285
• CHEBI ID: 9536
• ATC CODE: QN01AF90
• CHEMBL: 440
• Chemspider ID: 2297298
• DrugBank ID: DB01154
• KEGG ID: D06106
• Unique Ingredient Identifier: 01T23W89FR
• Wikipedia Title: Thiamylal

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.1973195
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.9151683
• LogD (pH = 7.4): 2.517312
• Log P: 2.9237015
• Molar Refractivity: 70.6389 cm^3
• Polarizability: 27.72023 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.11
• LOG S: -3.7
• Solubility (Water): 5.06e-02 g/l

PROPERTIES

Physical Property

• Solubility: 49.4 mg/L
• Hydrophobicity(logP): 2.5

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Drug Control: USDEA Schedule III; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Legal Status: Schedule III (Canada); Schedule III (US)

Product Information

• Grade: analytical standard

DETAILS

DrugBank - DB01154

• Drug Groups: approved
• Description: A barbiturate that is administered intravenously for the production of complete anesthesia of short duration, for the induction of general anesthesia, or for inducing a hypnotic state. (From Martindale, The Extra Pharmacopoeia, 30th ed, p919)
• Indication: Used for the production of complete anaesthesia of short duration, for the induction of general anaesthesia, and for inducing a hypnotic state.
• Pharmacology: Thiamylal, a barbiturate, is used in combination with acetaminophen or aspirin and caffeine for its sedative and relaxant effects in the treatment of tension headaches, migraines, and pain. 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: Intravenous LD50 in rat is 51 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Rapidly absorbed (high lipid solubility).
• Half Life: Although no studies have been performed on humans, the half-life in cats is 14.3 hours.
• External Links: Wikipedia

Sigma Aldrich - T9799

Biochem/physiol Actions
静脉内麻醉药

Toronto Research Chemicals - T344165

Thiamylal is a barbiturate derivative with sedative, anticonvulsant and hypnotic effects. Thiamylal is used for induction in surgical anaesthesia as well as an anticonvulsant to counteract side effects from other anaesthetics. Thiamylal is a Controlled Su

REFERENCES

• Hsieh, M.Y. et al.: Acta, Paediat. Tai., 46, 294 (2005)
• Lin C.K. et al.: Kaoh. J. Med. Sci., 26, 192 (2005)
• Tanaka, E. et al.: Neuriosci. Res., 64, 391 (2005)