Secobarbital

Secobarbital
Systematic (IUPAC) name
5-[(2R)-pentan-2-yl]-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Clinical data
Trade names Seconal
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a682386
Pregnancy cat. D (United States)
Legal status Schedule II (US)
Routes Oral
Pharmacokinetic data
Bioavailability  ?
Protein binding 45-60%[1]
Metabolism Hepatic
Half-life 15-40 hours[1]
Excretion Renal
Identifiers
CAS number 76-73-3 Y
ATC code N05CA06 QN51AA02
PubChem CID 5193
DrugBank APRD00497
ChemSpider 5005 Y
UNII 1P7H87IN75 Y
KEGG D00430 Y
ChEBI CHEBI:9073 Y
ChEMBL CHEMBL447 Y
Chemical data
Formula C12H18N2O3 
Mol. mass 238.283
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Secobarbital sodium (marketed by Eli Lilly and Company, and subsequently by other companies as described below, under the brand name Seconal) is a barbiturate derivative drug that was first synthesized in 1928 in Germany. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone.

Contents

Indications

Secobarbital is indicated for:

Availability

Ranbaxy Pharmaceuticals, an India-based company now predominantly owned by the Japanese company Daiichi Sankyo, obtained the rights to market Seconal from Eli Lilly in 1998 and did so until September 18, 2008. The rights to market Seconal were then sold to Marathon Pharmaceuticals, the current marketer. The date of return of 100 mg Seconal capsules can be confirmed by US distributor Cardinal and/or pharmacies such as King Soopers and Walgreens that carry or special order Marathon Seconal since 2009. Seconal returned to the market in January 2009.(see http://www.tititudorancea.com/z/secobarbital.htm) It is available as 100 mg. capsules, either as 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:

Side effects

Possible side effects of secobarbital include:

Withdrawal

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

Recreational use

Secobarbital began to be widely misused in the 1960s and 1970s, although with the advent of benzodiazepines, it has become less commonly used. Secobarbital has acquired many nicknames, the most common being reds, "red devils", 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.

Famous deaths related to use

Use as lethal injection

Secobarbital overdose was the most common method of implementing physician assisted suicide in Oregon for many years. Subsequently, pentobarbital has dominated in Oregon PAD. Ranbaxy Laboratories Limited previously experienced various issues in their attempts to produce 100 mg secobarbital capsules. Currently, Marathon Pharmaceuticals is the sole marketer of the drug in the United States, although the drug remains manufactured by Ohm Laboratories.

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

References

  1. ^ a b Lexi-Comp. "Secobarbital". http://www.merck.com/mmpe/lexicomp/secobarbital.html. 
  2. ^ Thomson, David,Film Studies: She couldn't act for toffee - until she burst into song; The Independent; 2004-06-27; Retrieved on 2007-01-26
  3. ^ Tennessee Williams' death myth - New York Post - February 15, 2010
  4. ^ De la Parra, Adolfo "Fito" (2000). Living the Blues: Canned Heat's Story of Music, Drugs, Death, Sex and Survival. Canned Heat Music. ISBN 0967644909. 
  5. ^ "Queen: The Life and Music of Dinah Washington" Nadine Cohodas 2004

External links