AMOBARBITAL

US Previously Marketed

First marketed in 1923

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H18N2O3
Molecular Weight	226.2722
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=VIROVYVQCGLCII-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C11H18N2O3
Molecular Weight	226.2722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/ppa/amobarbital-sodium.html

AMOBARBITAL is a barbiturate derivative with hypnotic and sedative properties. In an in vitro study in rat thalamic slices amobarbital worked by activating GABAA receptors, which decreased input resistance, depressed 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 increased both the amplitude and decay time of inhibitory postsynaptic currents. Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL1907607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6099281	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275 Sources: https://www.drugs.com/ppa/amobarbital-sodium.html	Primary		Approved 8583	Amytal Sodium Approved Use Unknown
Insomnia 111 Sources: https://www.drugs.com/ppa/amobarbital-sodium.html	Primary		Approved 8583	Amytal Sodium Approved Use Unknown

AUC

Value	Dose	Co-administered	Analyte	Population
56.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/975717/	120 mg single, intravenous dose: 120 mg route of administration: Intravenous experiment type: SINGLE co-administered:		AMOBARBITAL serum	Homo sapiens population: HEALTHY age: sex: MALE food status: FASTED
56.07 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/975717/	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:		AMOBARBITAL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
23.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/975717/	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:		AMOBARBITAL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
40% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/975717/			AMOBARBITAL plasma	Homo sapiens

Doses

Dose	Population	Adverse events
2 g single, oral Lethal dose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/493954/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/493954/	Disc. AE: Unconsciousness, Hypothermia... AEs leading to discontinuation/dose reduction: Unconsciousness Hypothermia Supraventricular arrhythmias Ventricular arrhythmia Convulsions Haematemesis Cardiac arrest (grade 5) Coma (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/493954/
15 g single, oral Overdose Dose: 15 g Route: oral Route: single Dose: 15 g Sources: https://pubmed.ncbi.nlm.nih.gov/12458639/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12458639/	Disc. AE: Convulsions, Delirium... AEs leading to discontinuation/dose reduction: Convulsions Delirium Cerebral hypoperfusion Sources: https://pubmed.ncbi.nlm.nih.gov/12458639/

AEs

AE	Significance	Dose	Population
Convulsions	Disc. AE	2 g single, oral Lethal dose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/493954/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/493954/
Haematemesis	Disc. AE	2 g single, oral Lethal dose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/493954/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/493954/
Hypothermia	Disc. AE	2 g single, oral Lethal dose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/493954/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/493954/
Supraventricular arrhythmias	Disc. AE	2 g single, oral Lethal dose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/493954/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/493954/
Unconsciousness	Disc. AE	2 g single, oral Lethal dose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/493954/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/493954/
Ventricular arrhythmia	Disc. AE	2 g single, oral Lethal dose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/493954/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/493954/
Cardiac arrest	grade 5 Disc. AE	2 g single, oral Lethal dose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/493954/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/493954/
Coma	grade 5 Disc. AE	2 g single, oral Lethal dose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/493954/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/493954/
Cerebral hypoperfusion	Disc. AE	15 g single, oral Overdose Dose: 15 g Route: oral Route: single Dose: 15 g Sources: https://pubmed.ncbi.nlm.nih.gov/12458639/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12458639/
Convulsions	Disc. AE	15 g single, oral Overdose Dose: 15 g Route: oral Route: single Dose: 15 g Sources: https://pubmed.ncbi.nlm.nih.gov/12458639/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12458639/
Delirium	Disc. AE	15 g single, oral Overdose Dose: 15 g Route: oral Route: single Dose: 15 g Sources: https://pubmed.ncbi.nlm.nih.gov/12458639/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12458639/

PubMed

Title	Date	PubMed
[The use of enzymatic hydrolysis for isolation of barbituric acid derivatives from blood (as exemplified by phenobarbital and barbamyl)].	2011-01-27	21265178
Identification of a novel phosphorylation site in hepatitis C virus NS5A.	2010-10	20592109
Prozone effect of serum IgE levels in a case of plasma cell leukemia.	2010-09-10	20828419
Temporary test occlusion of distal middle cerebral artery using GDC coil.	2010-04	19187477
Multiple myeloma presenting as CEA-producing rectal cancer.	2010-03-31	21139949
Changes in clinical trials methodology over time: a systematic review of six decades of research in psychopharmacology.	2010-03-03	20209133
Mutism as the presenting symptom: three case reports and selective review of literature.	2010-01	21799563
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Transitional Nerve: A New and Original Classification of a Peripheral Nerve Supported by the Nature of the Accessory Nerve (CN XI).	2010	21318044
Do mtDNA Mutations Participate in the Pathogenesis of Sporadic Parkinson's Disease?	2009-12	20514220
Perioperative modulating factors on astigmatism in sutured cataract surgery.	2009-12	20046682
Acquired and congenital disorders of sung performance: A review.	2009-11-12	20523851
The specificity of neuroprotection by antioxidants.	2009-11-05	19891782
Identification of a novel topoisomerase inhibitor effective in cells overexpressing drug efflux transporters.	2009-10-02	19798419
Stimulus type affects Wada memory performance.	2008-10	18639650
Skeletal muscle properties and fatigue resistance in relation to smoking history.	2008-09	18560879
Enigmatic effect of cellular ATP on fatty acid biosynthesis. Stimulation by moderate decrease and inhibition by increase of cellular ATP.	2008-06-25	18503772
Neuroprotective role of neurophysiological monitoring during endovascular procedures in the brain and spinal cord.	2007-12	18083497
[Applications of optical topography in neurosurgery].	2007-05	17533971
Preoperative cellulose porous beads for therapeutic embolization of meningioma: provocation test and technical considerations.	2007-05	17318600
Analysis of donors of electrons to photosystem I and cyclic electron flow by redox kinetics of P700 in chloroplasts of isolated bundle sheath strands of maize.	2007-04	17551845
Different states of energy metabolism in the vertebrate retina can be identified by stimulus-related changes in near UV transmission.	2007-04	16902788
Stimulation-induced changes in NADH fluorescence and mitochondrial membrane potential in lizard motor nerve terminals.	2007-03-15	17218351
Impaired cognition and attention in adults: pharmacological management strategies.	2007-02	19300541
Comorbid substance-use in schizophrenia: the file drawer effect, In reply to: Talamo et al., 2006. "Comorbid substance-use in schizophrenia: relation to positive and negative symptoms".	2007-02	17055705
Seizures during intracarotid methohexital and amobarbital testing.	2007-02	17049312
In silico prediction of pregnane X receptor activators by machine learning approaches.	2007-01	17003167
Amygdalohippocampal involvement in tinnitus and auditory memory.	2006-12	17114143
Ecto-5'-nucleotidase: Structure function relationships.	2006-06	18404474
Electron transport pathways for the oxidation of endogenous substrate(s) in Acidithiobacillus ferrooxidans.	2006-04	16699582
Amytal interview using intravenous lorazepam in a patient with dissociative fugue.	2006-03-31	17088173
Pharmacological interventions for spasticity following spinal cord injury: results of a Cochrane systematic review.	2006-03	16565680
Effects of electron transport inhibitors and uncouplers on the oxidation of ferrous iron and compounds interacting with ferric iron in Acidithiobacillus ferrooxidans.	2005-08	16234867
P2Y2 nucleotide receptor up-regulation in submandibular gland cells from the NOD.B10 mouse model of Sjögren's syndrome.	2005-06	15848146
Contribution of the PI 3-kinase/Akt survival pathway toward osmotic preconditioning.	2005-01	15786717
Endovascular management of dolichoectasia of the posterior cerebral artery report.	2004-12-01	15569748
Intracarotid Amytal memory test and hippocampal magnetic resonance imaging volumetry: validity of the Wada test as an indicator of hippocampal integrity among candidates for epilepsy surgery.	2004-12	15597752
[Rotenone-insensitive NADH oxydation in mitochondrial suspension occurs by NADH dehydrogenase of respiratory chain fragments].	2004-11-06	15526465
Selective GABA-receptor actions of amobarbital on thalamic neurons.	2004-10	15381635
Role of endothelial mitochondria in oxidant production and modulation of neutrophil adherence.	2004-03-29	15479985
Clinical experimental observations of carotid artery injections of sodium amytal.	1997-02	9056272
Regulation of hepatic nitric oxide synthase by reactive oxygen intermediates and glutathione.	1995-02-01	7532384
High-performance liquid chromatographic determination of the diastereomers of 1-(beta-D-glucopyranosyl)amobarbital in urine.	1987-11-27	3437019
Respiratory failure after clonazepam and amobarbital.	1986-11	3777263
Seven cases of somnambulism induced by drugs.	1979-07	453369
Amobarbital metabolism in man: N-glucoside formation.	1978-07	684279
Hypotensive effects of chlordiazepoxide, amobarbital and chlorpromazine on behaviorally induced elevated arterial blood pressure in the squirrel monkey.	1970-06	4988497
Hypomagnesemia with convulsions in a newborn infant. Report of a case associated with maternal hypophosphatemia.	1967-09-30	6069279
Dystonic reactions to prochlorperazine in hypoparathyroidism.	1966-11-03	5331863
The alcoholic metabolites of pentobarbital and amobarbital in man.	1965-10	5855308

Patents

Sample Use Guides

In Vivo Use Guide

Sedative: 30 to 50 mg given 2 or 3 times daily. Hypnotic: 65 to 200 mg at bedtime.

Route of Administration: Oral

In Vitro Use Guide

To 100mkl of the tissue homogenate were added 50 mkl of [3SS]TBPS (at the appropriate concentration, and made in 1 M NaBr), 50 mkl of 50 mM Tris Citrate buffer (to define total binding) or AMOBARBITAL at 100mkM or 50mkl of 40mkM picrotoxinin (to define nonspecific binding). The mixture was incubated 90 min at 21°C and then filtered over glass-fiber filters (Schleicher and Schuell No. 32). Filters were washed three times with 5 ml 0.9% (w:v) NaC1 equilibrated to 21°C and then counted by liquid scintillation spectrometry.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:21 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:21 GMT 2025`
Record UNII	GWH6IJ239E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMOBARBITAL

Official Name

English

AMOBARBITAL CII

Preferred Name

English

amobarbital [INN]

Common Name

English

ISOMYTAL

Brand Name

English

AMOBARBITAL [VANDF]

Common Name

English

AMOBARBITAL [MART.]

Common Name

English

AMOBARBITAL [JAN]

Common Name

English

AMOBARBITAL CII [USP-RS]

Common Name

English

5-Ethyl-5-isopentylbarbituric acid

Systematic Name

English

Amobarbital [WHO-DD]

Common Name

English

2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-ETHYL-5-(3-METHYLBUTYL)-

Systematic Name

English

AMOBARBITAL [EP IMPURITY]

Common Name

English

NSC-10815

Code

English

AMYTAL

Brand Name

English

AMOBARBITAL [HSDB]

Common Name

English

AMOBARBITAL [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN05CA02