CAS 77-27-0|thioseconal|Thioseconal|5-(pentan-2-yl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione|Surital|Thiamylal|thiamylal|Thiamylal|5-烯丙基-5-(1-甲基丁基)-2-硫代巴比妥酸|硫戊巴比妥...

General Information

Structure

Molecular Formula

C₁₂H₁₈N₂O₂S

Molecular Mass

254.34852

Exact Mass

254.10889883

Charge

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

Canonic Smiles

CCCC(C1(CC=C)C(=O)NC(=S)NC1=O)C

Isomeric Smiles

S=C1NC(=O)C(C(CCC)C)(CC=C)C(=O)N1

Calculated Properties

JChem

LogD (pH = 7.4)

2.52

LogD (pH = 5.5)

2.92

Log P

2.92

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

7.20

Polar Surface Area

58.20

Polarizability

26.59

Molar Refractivity

70.64

LOG S

-4.30

Data Source

Names and Identifiers

IUPAC Traditional name

thioseconal thiamylal

Brand Name

ThioseconalSurital

IUPAC name

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

Synonyms

ThiamylalThiamylal5-烯丙基-5-(1-甲基丁基)-2-硫代巴比妥酸硫戊巴比妥Bio-TalThioseconal5-Allyl-5-(1-methylbutyl)-2-thiobarbituric acidNSC 120815Dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-4,6(1H,5H)-pyrimidinedioneDihydro-5-(1-methylbutyl)-5-(2-propen-1-yl)-2-thioxo-4,6(1H,5H)-pyrimidinedioneThiamylalSuritalthiamylal5-allyl-5-(1-methylbutyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedioneThiamylalthioseconal5-Allyl-5-(1-methylbutyl)-2-thiobarbituric acid5-allyl-5-(1-methylbutyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dionedihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-4,6(1H,5H)-pyrimidinedione

Names and Identifiers

Registration numbers

Wikipedia Title

Thiamylal

KEGG ID

D06106C07846

PubChem SID

465062612490060516096448811533350

CAS Number

77-27-0

CHEMBL

440CHEMBL440

Chemspider ID

2297298

Unique Ingredient Identifier

PubChem CID

MDL Number

ATC CODE

CHEBI ID

DrugBank ID

EC Number

MetaboLights Database

MTBLS2406MTBLS1693

CompTox Database

DTXSID3048441

PubMed Citation Links

2043410024351886194306123852608

Patent number

KEGG DRUG Database

Reaxys Registry

ACToR Database

Drug Central Database

HMDB Database

SureChEMBL Database

Beilstein Number

LINCS Database

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.5

Solubility

49.4 mg/L

Pharmacology Properties

Legal Status

Schedule III (US)

Schedule III (Canada)

Product Information

analytical standard

Download link

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]