AMOBARBITAL SODIUM

US Previously Marketed

First marketed in 1923

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H17N2O3.Na
Molecular Weight	248.254
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CCC1(CCC(C)C)C(=O)NC(=O)[N-]C1=O

InChI

InChIKey=BNHGKKNINBGEQL-UHFFFAOYSA-M

InChI=1S/C11H18N2O3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

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

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 alcoholic metabolites of pentobarbital and amobarbital in man.	1965 Oct	5855308
Dystonic reactions to prochlorperazine in hypoparathyroidism.	1966 Nov 3	5331863
Seven cases of somnambulism induced by drugs.	1979 Jul	453369
Transient crossed aphasia and persistent amnesia after right thalamic haemorrhage.	2001 Oct	11595089
Wada testing reveals frontal lateralization for the memorization of words and faces.	2002 Jan 1	11798392
Key structural features of ligands for activation of human pregnane X receptor.	2004 Apr	15039302
Neurophysiologic monitoring and pharmacologic provocative testing for embolization of spinal cord arteriovenous malformations.	2004 Aug	15313696
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 Dec	15597752
Effects of electron transport inhibitors and uncouplers on the oxidation of ferrous iron and compounds interacting with ferric iron in Acidithiobacillus ferrooxidans.	2005 Aug	16234867
Contribution of the PI 3-kinase/Akt survival pathway toward osmotic preconditioning.	2005 Jan	15786717
P2Y2 nucleotide receptor up-regulation in submandibular gland cells from the NOD.B10 mouse model of Sjögren's syndrome.	2005 Jun	15848146
Electron transport pathways for the oxidation of endogenous substrate(s) in Acidithiobacillus ferrooxidans.	2006 Apr	16699582
Impaired cognition and attention in adults: pharmacological management strategies.	2007 Feb	19300541
In silico prediction of pregnane X receptor activators by machine learning approaches.	2007 Jan	17003167
Stimulation-induced changes in NADH fluorescence and mitochondrial membrane potential in lizard motor nerve terminals.	2007 Mar 15	17218351
Skeletal muscle properties and fatigue resistance in relation to smoking history.	2008 Sep	18560879
Mutism as the presenting symptom: three case reports and selective review of literature.	2010 Jan	21799563
Multiple myeloma presenting as CEA-producing rectal cancer.	2010 Mar 31	21139949
[The use of enzymatic hydrolysis for isolation of barbituric acid derivatives from blood (as exemplified by phenobarbital and barbamyl)].	2010 Sep-Oct	21265178

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 18:01:28 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:28 GMT 2025`
Record UNII	G0313KNC7D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMOBARBITAL SODIUM

Common Name

English

AMOBARBITAL SODIUM FOR INJECTION

Preferred Name

English

Amobarbital sodium [WHO-DD]

Common Name

English

Sodium 5-ethyl-5-isopentylbarbiturate

Systematic Name

English

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

Common Name

English

AMOBARBITAL SODIUM [USP MONOGRAPH]

Common Name

English

AMOBARBITAL SODIUM [VANDF]

Common Name

English

AMYTAL SODIUM

Brand Name

English

AMOBARBITAL SODIUM FOR INJECTION [JAN]

Common Name

English

AMOBARBITAL SODIUM SALT

Common Name

English

AMOBARBITAL SODIUM [MART.]

Common Name

English

TALAMO

Brand Name

English

AMYLOBARBITONE SODIUM

Common Name

English

AMOBARBITAL SODIUM SALT [MI]

Common Name

English

AMOBARBITAL SODIUM [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

DEA NO.

2125