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Secobarbital

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Secobarbital chemical structure
Secobarbital

5-(1-methylbutyl)-5-prop-2-enyl-
hexahydropyrimidine-2,4,6-trione

IUPAC name
CAS number
76-73-3
ATC code

N05CA06

PubChem
5193
DrugBank
APRD00497
Chemical formula {{{chemical_formula}}}
Molecular weight 238.283
Bioavailability  ?
Metabolism Hepatic
Elimination half-life 15-40 hours[1]
Excretion Renal
Pregnancy category D (USA)
Legal status {{{legal_status}}}
Routes of administration Oral


Secobarbital (marketed by Eli Lilly and Company under the brand name Seconal®) is a barbiturate derivative drug. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone.

IndicationsEdit

Secobarbital is indicated for:

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

AvailabilityEdit

File:Secobarbital DOJ.jpg

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 sodiumEdit

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 effectsEdit

Side effects of secobarbital include:

WithdrawalEdit

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

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

Recreational useEdit

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, or "red dillies" (it was originally packaged in red capsules). Another common nickname is "seccies". Another common nickname is "red hearts" according to the Wegman's School of Pharmacy curriculum. 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 injectionEdit

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 100 mg secobarbital capsules, but there is no longer a shortage as of October 2006.

It is a component in the veterinary drug Somulose, used for euthanasia of horses and cattle.

ReferencesEdit

  1. Lexi-Comp. Secobarbital.

External linksEdit


Barbiturates edit

Allobarbital, Amobarbital, Aprobarbital, Barbexaclone, Barbital, Butabarbital, Butalbital, Butobarbital, Cyclobarbital, Ethallobarbital, Heptabarbital, Hexobarbital, Mephobarbital, Metharbital, Methohexital, Methylphenobarbital, Pentobarbital, Phenobarbital, Primidone, Proxibarbal, Reposal, Secobarbital, Talbutal, Thiobarbital, Thiopental, Vinbarbital, Vinylbital


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