Article: Secobarbital

Secobarbital
Systematic (IUPAC) name
5-(1-methylbutyl)-5-prop-2-enyl- hexahydropyrimidine-2,4,6-trione
Identifiers
CAS number	76-73-3
ATC code	N05CA06
PubChem	5193
DrugBank	APRD00497
Chemical data
Formula	C12H18N2O3
Mol. weight	238.283
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Half life	?
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	D (USA)
Legal status	Schedule II (USA)
Routes	Oral

Secobarbital (marketed under the brand names Seconal® and Tuinal) is a drug which is a barbiturate derivative. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. Was previously known as quinalbarbitone in the UK (former BAN).

Indications

Secobarbital is indicated for:

• Treatment of epilepsy
• Temporary treatment of insomnia in patients habituated to barbiturates
• Use as a preoperative medication to produce anaesthesia and anxiolysis in short surgical, diagnostic, or therapeutic procedures which are minimally painful.

Availability

It is available as either a free acid or a sodium salt. The free acid is a white amorphous powder that is slightly soluble in water and very soluble in ethanol. The salt is a white hygroscopic powder that is soluble in water and ethanol.

Secobarbital sodium

The sodium salt of secobarbital is classified separately from the free acid, as follows:

• CAS number: 309-43-3
• Chemical formula: C₁₂H₁₈N₂NaO₃
• Molecular weight: 260.265

Side effects

Side effects of secobarbital include:

• Somnolence
• Impaired motor functions
  • Impaired coordination
  • Impaired balance
  • Dizziness
• Anxiety
• Confusion
• Agitation, irritability, or excitability
• Headache
• Nausea
• Vomiting
• Nightmares
• Increased sensitivity to pain
• Allergic reactions
  • Difficulty breathing
  • Edema
  • Urticaria

Withdrawal

Secobarbital is a fairly addictive drug, and withdrawal symptoms can occur when if long-term usage is abruptly ended. Withdrawal symptoms can include:

• Insomnia
• REM rebound
• Anxiety
• Tremors
• Seizures
• Lack of appetite

Recreational use

Secobarbital began to be widely abused in the 1960s and 1970s, although with the advent of benzodiazepines, they have become less commonly used.

Secobarbital has acquired many nicknames, the most common being "reds" (it was originally packaged in red capsules). Another common nickname is "seccies". A less common nickname is "dolls"; this was partly responsible for the title of Jacqueline Susann's novel Valley of the Dolls, whose main characters use secobarbital and other such drugs.

Another popular brand of barbiturate pill Tuinal contained a combination of secobarbital and amobarbital but is now rarely prescribed due to problems with abuse and overdose.

Use as a lethal injection

Secobarbital overdose was the most common method of implementing physician-assisted suicide (PAS) in Oregon until Eli Lilly and Company discontinued manufacturing it in May 2001, leading to a shortage of the drug. Since then, pentobarbital has dominated in Oregon PAS. Ranbaxy Laboratories Limited have experienced approval issues in their attempts to produce secobarbital, but the shortage is expected to end in January 2006.