57-43-2

Basic information

• Product Name: Amobarbital
• Synonyms: 5-Ethyl-d5-5-(3-methylbutyl)-2,4,6-(1H,3H,5H)-pyrimidinetrione;Mylodor;AMOBARBITOL;Amobarbital (base and/or unspecified salts);5-Ethyl-5-isopentylpyrimidine-2,4,6(1H,3H,5H)-trionE;5-Ethyl-5-isobarbituric acid;Methanol（Test Amobarbital, 1.0 mg/mL）;Amobarbital CII (200 mg)
• CAS NO: 57-43-2
• Molecular Formula: C₁₁H₁₈N₂O₃
• Molecular Weight: 226.27
• EINECS: 200-330-7
• Product Categories: Miscellaneous;Intermediates & Fine Chemicals;Isotope Labeled Compounds;Pharmaceuticals;Heterocycles
• Mol File: 57-43-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 156-158°C
• Boiling Point: 367.89°C (rough estimate)
• Flash Point: 9℃
• Appearance: white crystalline powder
• Density: 1.1376 (rough estimate)
• Refractive Index: 1.4620 (estimate)
• Storage Temp.: ?20°C
• PKA: 8.0(at 25℃)
• Water Solubility: <0.1 g/100 mL at 18.5℃
• Stability: Stable. Incompatible with strong oxidizing agents. Hygroscopic.
• CAS DataBase Reference: Amobarbital(CAS DataBase Reference)
• NIST Chemistry Reference: Amobarbital(57-43-2)
• EPA Substance Registry System: Amobarbital(57-43-2)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45
• RIDADR: 3249
• WGK Germany: 1
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 57-43-2(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Originator

Hypnotal,Pharmacal

Uses

Different sources of media describe the Uses of 57-43-2 differently. You can refer to the following data:
1. Controlled substance (depressant). Sedative, hypnotic
2. Amobarbital for binding at complex I to inhibit mitochondrial electron transport. Amobarbital is regulated as a schedule II compound in the United States and intended only for forensic and research purposes. This product is a qualified Reference Material (RM) that has been manufactured and tested to meet ISO17025 and Guide 34 guidelines. These materials are tested using validated analytical methods on qualified instrumentation to ensure traceability of measurements. All traceable RMs may be distinguished by their CofAs and can be downloaded below using the batch number located on the product label. For a representative CofA please contact our technical support.

Definition

ChEBI: A member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by a 3-methylbutyl and an ethyl group at position 5. Amobarbital has been shown to exhibit sedative and hy notic properties.

Manufacturing Process

By interaction of malonic acid diethyl ester with sodium ethylate (molar ratio 1:1) and then with ethyl bromide (molar ratio 1:1) was prepared ethylmalonic acid diethyl ester. From ethylmalonic acid diethyl ester and sodium ethylate (molar ratio 1:1) and then with isopentylbromide was synthesized α-ethyl-α- isopentylmalonic acid diethyl ester. By condensation of α-ethyl-α- isopentylmalonic acid diethyl ester with urea in the presence of sodium ethylate was obtained ethyl-isopentylbarbituric acid.

Brand name

Amytal Sodium (Lilly); Talamo (Marion Merrell Dow);Altinal;Alupent-sed;Ambese-la;Amobell;Amsal;Amycal;Amydorm;Amylbarb;Amylobeta;Analgilasa;Appenil;Asthmin;Beatol;Bludex;Calavon;Cuaot;Dexaspan;Dexital;Ergo-lonarid;Estimal;Etamyl;Ifenin;Isoamitil sedante;Isobec;Jalonac;Lonarid n;Medi-trol;Mudeka;Mylodorm sustrel;N 8;Neur-amyl;Novambobarb;Novogen;Obe_slim;Placidel;Protasma;Sedo-rythmodan;Sy-dexam;Transital.

Therapeutic Function

Hypnotic, Antiepileptic

World Health Organization (WHO)

Amobarbital is an intermediate-acting barbiturate which is controlled under Schedule III of the 1971 Convention on Psychotropic Substances. See WHO comment for barbiturates. (Reference: (UNCPS3) United Nations Convention on Psychotropic Substances (III), , , 1971)

General Description

White crystalline solid with no odor and a slightly bitter taste.

Air & Water Reactions

Amobarbital is hygroscopic . Insoluble in water.

Reactivity Profile

Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Hazard

May be a habit forming drug of abuse.

Fire Hazard

Flash point data for Amobarbital are not available, however, Amobarbital is probably combustible.

Safety Profile

A poison by ingestion,intravenous, intraperitoneal, and subcutaneous routes. Seealso BARBITURATES. When heated to decomposition itemits toxic fumes of NOx.

InChI:InChI=1/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)

Upstream product

• 66778-09-4 ethyl-isopentyl-malonic acid diamide 
• 57-13-6 urea 
• 77-24-7 diethyl ethylisopentylmalonate 
• 75077-34-8 diethyl ethylisoamylmalonurate 
• 4388-79-8 5-ethyl-5-(3-methylbutyl)-2-thiobarbituric acid 
• 6082-49-1 ethyl propanediamide 

Downstream Products

• 65944-31-2 5-ethyl-5-(3-methyl-butyl)-1,3-bis-(4-nitro-benzyl)-pyrimidine-2,4,6-trione 
• 73680-98-5 1-benzyl-5-ethyl-5-(3-methyl-butyl)-pyrimidine-2,4,6-trione 
• 28239-46-5 1,3-Dimethyl-5-aethyl-5-isoamyl-barbitursaeure 
• 1421-07-4 γ-hydroxyamobarbital 
• 102450-10-2 Isoamyl-ethyl-acetamid 
• 119410-34-3 5-Ethyl-1-(3-iodo-benzoyl)-5-(3-methyl-butyl)-pyrimidine-2,4,6-trione 
• 119410-33-2 5-Ethyl-1-(2-iodo-benzoyl)-5-(3-methyl-butyl)-pyrimidine-2,4,6-trione 
• 119422-06-9 5-Ethyl-1-(4-fluoro-benzoyl)-5-(3-methyl-butyl)-pyrimidine-2,4,6-trione 
• 119410-32-1 1-(3-Chloro-benzoyl)-5-ethyl-5-(3-methyl-butyl)-pyrimidine-2,4,6-trione 
• 119410-31-0 1-(2-Chloro-benzoyl)-5-ethyl-5-(3-methyl-butyl)-pyrimidine-2,4,6-trione 
• 67019-65-2 1-(4-chloro-benzoyl)-5-ethyl-5-(3-methyl-butyl)-pyrimidine-2,4,6-trione 
• 119410-30-9 5-Ethyl-1-(3-fluoro-benzoyl)-5-(3-methyl-butyl)-pyrimidine-2,4,6-trione 
• 119410-29-6 5-Ethyl-1-(2-fluoro-benzoyl)-5-(3-methyl-butyl)-pyrimidine-2,4,6-trione 
• 119410-35-4 5-Ethyl-1-(4-iodo-benzoyl)-5-(3-methyl-butyl)-pyrimidine-2,4,6-trione 

Relevant articles and documents

Preparation and purification method of 5-ethyl-5-isoamyl malonyl urea

The invention provides a preparation and purification method for preparing 5-ethyl-5-isoamyl malonyl urea. The preparation and purification method has the advantages of stable process, no special requirements on the concentration of sodium methoxide, direct use of industrial products in the reaction process, easy control of reaction conditions, short reaction time, simple operation, less three wastes, good product quality, high yield, effective reduction of the impurity content, improvement of the quality of the target product, low production cost, and suitableness for industrial production.

Synthesis and cyclization of dialkylmalonuric esters

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