ContaminantDB: Amobarbital

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2014-08-30 21:04:32 UTC

Update Date

2026-05-14 16:59:43 UTC

Accession Number

CHEM003521

Identification

Common Name

Amobarbital

Class

Small Molecule

Description

A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565)

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Drug
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Ethyl-5-(3-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Ethyl-5-(3-methylbutyl)barbituric acid	ChEBI
5-Ethyl-5-isoamylbarbituric acid	ChEBI
5-Ethyl-5-isopentylbarbituric acid	ChEBI
Amylobarbitone	ChEBI
Amytal	ChEBI
Barbamil	ChEBI
Barbamyl	ChEBI
Isomytal	Kegg
5-Ethyl-5-(3-methylbutyl)barbitate	Generator
5-Ethyl-5-(3-methylbutyl)barbitic acid	Generator
5-Ethyl-5-isoamylbarbitate	Generator
5-Ethyl-5-isoamylbarbitic acid	Generator
5-Ethyl-5-isopentylbarbitate	Generator
5-Ethyl-5-isopentylbarbitic acid	Generator
Adams brand OF amorbarbital	HMDB
Amorbarbital miquel brand	HMDB
ICN brand OF amorbarbital	HMDB
Sodium amobarbital	HMDB
Amobarbital, sodium	HMDB
Amsal	HMDB
Amylbarb sodium	HMDB
Amytal sodium	HMDB
Hosbon brand OF amorbarbital	HMDB
Lilly brand OF amobarbital sodium	HMDB
Neur-amyl	HMDB
NeurAmyl	HMDB
Pentymal	HMDB
Protea brand OF amobarbital sodium	HMDB
Amobarbital sodium	HMDB
Amylobeta	HMDB
Bramble brand OF amobarbital sodium	HMDB
Eunoctal	HMDB
Fawns and mcallan brand OF amorbarbital	HMDB
Flynn brand OF amobarbital sodium	HMDB
Houdé brand OF amobarbital sodium	HMDB
Isoamitil sedante	HMDB
Lilly brand OF amobarbital	HMDB
Novopharm brand OF amobarbital sodium	HMDB
Placidel	HMDB
Sodium amytal	HMDB
Adams brand OF amobarbital sodium	HMDB
Flynn brand OF amobarbital	HMDB
Isonal	HMDB
Miquel brand OF amorbarbital	HMDB
Novamobarb	HMDB
Sodium, amobarbital	HMDB
Transital	HMDB

Chemical Formula

C₁₁H₁₈N₂O₃

Average Molecular Mass

226.272 g/mol

Monoisotopic Mass

226.132 g/mol

CAS Registry Number

57-43-2

IUPAC Name

5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione

Traditional Name

amobarbital

SMILES

CCC1(CCC(C)C)C(=O)NC(=O)NC1=O

InChI Identifier

InChI=1S/C11H18N2O3/c1-4-11(6-5-7(2)3)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)

InChI Key

VIROVYVQCGLCII-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

Pyrimidone
Hydropyrimidine
2,5-dihydropyrimidine
Carbonic acid derivative
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

barbiturates (CHEBI:2673 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	157 °C
Boiling Point	Not Available
Solubility	603 mg/L (at 25 °C)

Predicted Properties

Property	Value	Source
Water Solubility	0.9 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.89	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	7.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	58 m³·mol⁻¹	ChemAxon
Polarizability	23.45 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-004i-0090000000-5962005393da49f25b6d	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-3900000000-4b439f0aa2820ea498c7	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-004i-0090000000-5962005393da49f25b6d	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-3900000000-4b439f0aa2820ea498c7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9620000000-6298f9a27728bfc9722a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1390000000-7c25547f91d65d34b75e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-4900000000-0c36377cb01094db4c2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-fa8c8d196256959bdd9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0036-7950000000-45e6dd876654c6919ca7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9610000000-40925dd102ce4be321f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9600000000-e4f4b95f285a9be2c43a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-48d9a204e1fb509f9844	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3900000000-203e128dc6607ceba540	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-8900000000-3bee53e0f49ce37552a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-ff2ca28a72e0e94de818	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9040000000-ec4b92281eba0906d9e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-cffa2ffcfdf19b76d1d3	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-4900000000-8b443325c415e154ac85	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Amobarbital (like all barbiturates) works by binding to the GABAA receptor at either the alpha or the beta sub unit. These are binding sites that are distinct from GABA itself and also distinct from the benzodiazepine binding site. Like benzodiazepines, barbiturates potentiate the effect of GABA at this receptor. This GABAA receptor binding decreases input resistance, depresses burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increases both the amplitude and decay time of inhibitory postsynaptic currents. In addition to this GABA-ergic effect, barbiturates also block the AMPA receptor, a subtype of glutamate receptor. Glutamate is the principal excitatory neurotransmitter in the mammalian CNS. Amobarbital also appears to bind neuronal nicotinic acetylcholine receptors.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available