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Thiamylal

PubChem CID
3032285
Structure
Thiamylal_small.png
Thiamylal_3D_Structure.png
Molecular Formula
Synonyms
  • thiamylal
  • Thioseconal
  • Surital
  • 77-27-0
  • 5-Allyl-5-(1-methylbutyl)-2-thiobarbituric acid
Molecular Weight
254.35 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-25
Description
Thiamylal is a member of the class of barbiturates that is 2-thioxodihydropyrimidine-4,6(1H,5H)-dione substituted by a pentan-2-yl and prop-2-en-1-yl group at position 5. It has a role as a sedative. It is a member of barbiturates and an organosulfur compound.
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)
THIAMYLAL is a small molecule drug with a maximum clinical trial phase of IV that was first approved in 1982.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Thiamylal.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-pentan-2-yl-5-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 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)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

XLOMZPUITCYLMJ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCC(C)C1(C(=O)NC(=S)NC1=O)CC=C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C12H18N2O2S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

1340-07-4, 7187-63-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 KEGG ID

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 NSC Number

2.3.15 PharmGKB ID

2.3.16 Pharos Ligand ID

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Sodium, Thiamylal
  • Surital
  • Thiamylal
  • Thiamylal Sodium
  • Thioquinalbarbitone

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
254.35 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
254.10889899 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
254.10889899 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
90.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
17
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
346
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Melting Point

132-133 °C
PhysProp
132 - 133 °C

3.2.3 Solubility

49.4 mg/L (at 25 °C)
YALKOWSKY,SH & DANNENFELSER,RM (1992)
5.06e-02 g/L

3.2.4 LogP

3.23
HANSCH,C ET AL. (1995)
2.5

3.2.5 LogS

-3.46
ADME Research, USCD

3.2.6 Dissociation Constants

pKa
7.48
SANGSTER (1994)

3.2.7 Collision Cross Section

156.95 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

151.08 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

159.23 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

148.4 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

3.2.8 Kovats Retention Index

Standard non-polar
1886 , 1886 , 1873 , 1899
Semi-standard non-polar
1928.2

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Human drug -> Discontinued

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 10
View All
Spectra ID
Instrument Type
CI-B
Ionization Mode
positive
Top 5 Peaks

255.0 99.99

256.0 15

213.0 8

257.0 6

229.0 3

Thumbnail
Thumbnail
Notes
instrument=Unknown
2 of 10
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Unknown
Instrument Type
CI-B
Ionization Mode
positive
Top 5 Peaks

255 99.99

256 15

213 8

257 6

229 3

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.1.2 LC-MS

1 of 6
View All
Authors
Koji Yamaguchi, Department of Legal Medicine, Nippon Medical School, 1715 Kamagari, Inzai-shi, Chiba 270-1694, Japan.
Instrument
LCMS-8040 coupled to Nexera XR (Shimadzu, Kyoto, Japan).
Instrument Type
LC-ESI-QQ
MS Level
MS
Ionization Mode
NEGATIVE
Ionization
ESI
Column Name
InertSustain C18 ID 2.1 microm, 2.1 x 100 mm (GL Science, Tokyo, Japan).
Retention Time
9.279 min
Top 5 Peaks

253.1 999

254.1 140

255.1 58

321.1 11

Thumbnail
Thumbnail
License
CC BY
2 of 6
View All
Authors
Koji Yamaguchi, Department of Legal Medicine, Nippon Medical School, 1715 Kamagari, Inzai-shi, Chiba 270-1694, Japan.
Instrument
LCMS-8040 coupled to Nexera XR (Shimadzu, Kyoto, Japan).
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
10 V
Fragmentation Mode
CID
Column Name
InertSustain C18 ID 2.1 microm, 2.1 x 100 mm (GL Science, Tokyo, Japan).
Retention Time
9.279 min
Precursor m/z
253.101614
Precursor Adduct
[M-H]-
Top 5 Peaks

253.1 999

58.1 91

101 42

Thumbnail
Thumbnail
License
CC BY

4.1.3 Other MS

Authors
YOSHIZUMI H, FAC. OF PHARMACY, MEIJO UNIV.
Instrument
Unknown
Instrument Type
CI-B
MS Level
MS
Ionization Mode
POSITIVE
Top 5 Peaks

255 999

256 150

213 80

257 60

229 30

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.2 IR Spectra

4.2.1 FTIR Spectra

Instrument Name
Bio-Rad FTS
Technique
KBr0
Source of Spectrum
Forensic Spectral Research
Source of Sample
Alltech Associates, Inc., Grace Davison Discovery Sciences
Catalog Number
01732
Lot Number
420
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2.2 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Alltech Associates, Inc., Grace Davison Discovery Sciences
Catalog Number
01732
Lot Number
420
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Alltech Associates, Inc., Grace Davison Discovery Sciences
Catalog Number
01732
Lot Number
420
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Used for the production of complete anaesthesia of short duration, for the induction of general anaesthesia, and for inducing a hypnotic state.

7.2 Clinical Trials

7.2.1 NIPH Clinical Trials Search of Japan

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

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.

8.2 MeSH Pharmacological Classification

Anesthetics, Intravenous
Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174) (See all compounds classified as Anesthetics, Intravenous.)
GABA Modulators
Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)
Hypnotics and Sedatives
Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

8.3 Absorption, Distribution and Excretion

Absorption
Rapidly absorbed (high lipid solubility).

8.4 Metabolism / Metabolites

Hepatic.

8.5 Biological Half-Life

Although no studies have been performed on humans, the half-life in cats is 14.3 hours.

8.6 Mechanism of Action

Thiamylal 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.

8.7 Human Metabolite Information

8.7.1 Cellular Locations

Membrane

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Signal
Danger
GHS Hazard Statements

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation]

Precautionary Statement Codes

P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Acute Tox. 3 (100%)

Acute Tox. 3 (100%)

Acute Tox. 3 (100%)

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

13.2 Drug-Drug Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 NCI Thesaurus Tree

15.3 ChEBI Ontology

15.4 KEGG: Target-based Classification of Drugs

15.5 KEGG: Drug Groups

15.6 ChemIDplus

15.7 UN GHS Classification

15.8 NORMAN Suspect List Exchange Classification

15.9 CCSBase Classification

15.10 EPA DSSTox Classification

15.11 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
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  5. EPA DSSTox
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    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
    LICENSE
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    https://echa.europa.eu/web/guest/legal-notice
    5-allyl-5-(1-methylbutyl)-2-thiobarbituric acid (EC: 201-018-3)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/25226
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    http://www.hmdb.ca/citing
  9. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  10. ChEBI
  11. Open Targets
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    https://platform-docs.opentargets.org/licence
  12. ChEMBL
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    http://ctdbase.org/about/legal.jsp
  14. Therapeutic Target Database (TTD)
  15. IUPAC Digitized pKa Dataset
    pyrimidine, 5-allyl-5,6-dihydro-4-hydroxy-2-mercapto-5-(1-methylbutyl)-6-oxo-
    https://github.com/IUPAC/Dissociation-Constants
  16. Drugs@FDA
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  18. NIST Mass Spectrometry Data Center
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    https://www.nist.gov/srd/public-law
  19. SpectraBase
  20. Japan Chemical Substance Dictionary (Nikkaji)
  21. KEGG
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    https://www.kegg.jp/kegg/legal.html
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  22. MassBank Europe
  23. Metabolomics Workbench
  24. NCI Thesaurus (NCIt)
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  35. NORMAN Suspect List Exchange
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    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  36. MolGenie
    MolGenie Organic Chemistry Ontology
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  37. PATENTSCOPE (WIPO)
  38. NCBI
CONTENTS