5-Ethyl-5-(1,3-dimethylbut-1'-enyl)barbituric acid

5-Ethyl-5-(1,3-dimethylbut-1'-enyl)barbituric acid is a chemical compound belonging to the class of barbiturates. Barbiturates are derivatives of barbituric acid and act as central nervous system depressants. This particular compound is a synthetic derivative with specific structural modifications that influence its pharmacological properties.

Chemical Structure and Properties

5-Ethyl-5-(1,3-dimethylbut-1'-enyl)barbituric acid is characterized by the presence of an ethyl group and a 1,3-dimethylbut-1'-enyl group attached to the barbituric acid core. The chemical formula is C12H18N2O3, and it has a molecular weight of 238.29 g/mol.

Synthesis

The synthesis of 5-Ethyl-5-(1,3-dimethylbut-1'-enyl)barbituric acid involves the alkylation of barbituric acid with appropriate alkyl halides under controlled conditions. The reaction typically requires a base to deprotonate the barbituric acid, facilitating the nucleophilic attack on the alkyl halide.

Physical Properties

This compound is typically a crystalline solid at room temperature. It is sparingly soluble in water but more soluble in organic solvents such as ethanol and chloroform.

Pharmacology

Barbiturates, including 5-Ethyl-5-(1,3-dimethylbut-1'-enyl)barbituric acid, act by enhancing the activity of the neurotransmitter gamma-aminobutyric acid (GABA) at the GABA_A receptor. This results in increased inhibitory effects in the central nervous system, leading to sedation, hypnosis, and in higher doses, anesthesia.

Clinical Use

While barbiturates were once widely used for their sedative and hypnotic properties, their use has declined due to the development of safer alternatives such as benzodiazepines. However, certain barbiturates are still used in specific clinical settings, such as in the treatment of epilepsy and for inducing anesthesia.

Side Effects and Risks

Barbiturates can cause a range of side effects, including drowsiness, dizziness, and respiratory depression. They have a narrow therapeutic index, meaning the difference between a therapeutic dose and a toxic dose is small. Overdose can lead to severe respiratory depression and death.

Regulation and Legal Status

Due to their potential for abuse and dependence, barbiturates are classified as controlled substances in many countries. The specific legal status of 5-Ethyl-5-(1,3-dimethylbut-1'-enyl)barbituric acid may vary depending on local regulations.

Also see

• Barbituric acid
• Central nervous system depressants
• GABA_A receptor
• Sedative-hypnotic drugs