Secobarbital
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| Image:Secobarbital.png | |
| 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 by Eli Lilly and Company under the brand names Seconal® and Tuinal) is a barbiturate derivative drug. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it is known as Quinalbarbitone.
Contents |
[edit] 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.
[edit] 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.
[edit] 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
[edit] 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
[edit] Withdrawal
Secobarbital is a fairly addictive drug, and withdrawal symptoms can occur if long-term usage is abruptly ended. Withdrawal symptoms can include:
- Insomnia
- REM rebound
- Anxiety
- Tremors
- Seizures
- Lack of appetite
[edit] 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.
[edit] Role in death of Jimi Hendrix
Secobarbital played a role in the September 18, 1970 death of legendary rock guitarist Jimi Hendrix, who purportedly took nine Secobarbital tablets after a night of drinking wine and was later found dead in his London apartment. Hendrix' death was caused by asphyxiation, after Hendrix presumably vomited in his sleep as a result of the mixture of the excessive Secobarbital dose and alcohol.
[edit] Cause of Death of Judy Garland
Judy Garland, of "The Wizard of Oz" fame, was found dead in her bathroom by her husband Mickey Deans on June 22, 1969. The stated exact cause of death by coroner Gavin Thursdon was accidental overdose of barbiturates; pathologist Dr. R. Pocock found 4.9 mg of Seconal in Garland's blood.
[edit] 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.
[edit] External links
- Drugs.com - Secobarbital
- RxList.com - Secobarbital Consumer information.
