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| Clinical data | |
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| Trade names | Seconal, others |
| Other names | Quinalbarbitone |
| AHFS/Drugs.com | Consumer Drug Information |
| MedlinePlus | a682386 |
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| Routes of administration | By mouth,intravenous |
| Drug class | Barbiturate |
| ATC code | |
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| Pharmacokinetic data | |
| Bioavailability | ? |
| Protein binding | 45-60%[2] |
| Metabolism | Hepatic |
| Eliminationhalf-life | 15-40 hours[2] |
| Excretion | Renal |
| Identifiers | |
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| IUPHAR/BPS | |
| DrugBank |
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| ChemSpider |
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| UNII | |
| KEGG |
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| ChEBI | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.000.894 |
| Chemical and physical data | |
| Formula | C12H18N2O3 |
| Molar mass | 238.287 g·mol−1 |
| 3D model (JSmol) | |
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Secobarbital, sold under the brand nameSeconal among others, is a short-actingbarbiturate drug originally used for the treatment ofinsomnia. It was patented byEli Lilly and Company in 1934 in the United States.[3] It possessesanesthetic,anticonvulsant,anxiolytic,sedative, andhypnotic properties. In the United Kingdom, it was known asquinalbarbitone. Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill) and has largely been replaced by thebenzodiazepine family. It was widelyabused, known on the street as "red devils" or "reds."[4] Among barbiturates, secobarbital carries a particularly high risk of abuse andaddiction, which is largely responsible for it falling out of use.
Secobarbital is used for managing symptoms ofepilepsy and for short-term treatment ofinsomnia. It is also used as a preoperative medication to produceanesthesia andanxiolysis for short surgical, diagnostic, or therapeutic procedures which are minimally painful.[citation needed]
Secobarbital was widely abused for recreational purposes in the 1960s, 1970s, and 1980s, and accidental overdose was associated with the drug. Lilly's Seconal came in a bright orange/red bullet shaped capsule known as a Pulvule. Prescription use of secobarbital decreased beginning in the early 1980s by which timebenzodiazepines had become increasingly common. Secobarbital has acquired many nicknames, the most common being "reds," "red devils," or "red dillies" (because of the color of the capsules). Other common nicknames are "seccies," "Cardinals," "ruby slippers," and, according to the Wegman's School of Pharmacy curriculum, "red hearts". A less common nickname is "dolls"; this was partly responsible for the title ofJacqueline Susann's novelValley of the Dolls, whose main characters use secobarbital and other such drugs.[citation needed]
ActressesCarole Landis,Judy Garland, playwrightTennessee Williams, and journalistDorothy Kilgallen allegedly either died by suicide or of accidentally overdosing on secobarbital.[5] Seconal was used to induceFred Hampton into docility before he was then killed in his bed in the early hours of December 4, 1969.[6]
In 1978, 1,000 pills of Seconal were recovered inJonestown, along with substantial quantities ofValium,Thorazine,Talwin,Demerol, and othersedatives,hypnotics, andanalgesics.[7]
Human
Secobarbital is used in assisted dying, eithereuthanasia orpalliative sedation.[8][9][10]
In theNetherlands, individuals have two options forassisted dying: they can orally consume 100 mL of concentrated syrup containing either 15 grams ofpentobarbital or 15 grams of secobarbital, or they can choose to have 2 grams ofthiopental or 1 gram ofpropofol administeredintravenously by a doctor, followed by amuscle relaxant.[11] As of 2010, only 15% of those who died by physician-assisted suicide opted for orally consuming the lethal drug(s), the rest choosing to have the drugs administered intravenously by a doctor instead.[12]
In the United States, secobarbital and pentobarbital are the most common drugs prescribed underphysician aid-in-dying laws in Oregon since 1998, Washington since 2008, and Vermont since 2013.[13][14][10]Ranbaxy Laboratories Limited previously experienced various issues in their attempts to produce 100 mg secobarbital capsules.
In 2017, secobarbital was made available for physician-assisted suicide in Canada.[15]
Animal
It is a component in theveterinary drugSomulose, used foreuthanasia ofhorses andcattle.
TheLD50 of secobarbital has been reported to be between 125 mg/kg (rat, oral) and 267 mg/kg (mouse, oral).[16]
Possible side effects of secobarbital include:
Secobarbital may produce psychologicaladdiction and produces physicaldependence if used for an extended period of time.[21]Withdrawal symptoms may occur if long-term use is abruptly ended and can include:
Ranbaxy Pharmaceuticals, an India-based company now predominantly owned by the Japanese companyDaiichi Sankyo, obtained the rights to market and to use the trade name Seconal from Eli Lilly in 1998 and did so until September 2008. The actual manufacturer of Seconal subsequent to the time Eli Lilly manufactured the drug was Ohm Pharmaceuticals, a wholly owned subsidiary of Ranbaxy. The rights to market Seconal were then sold to Marathon Pharmaceuticals,[23] which became the marketer and trade-name holder. At the time Marathon Pharmaceuticals obtained ownership of the brand name, the retail price for one 100 mg capsule (depending upon prescription size and pharmacy) averaged about one U.S. dollar. During the time Marathon owned the brand name, the company greatly increased the price of the drug. By February 2015, when Marathon sold the rights toValeant Pharmaceuticals,[24] the average retail price per 100 mg capsule had risen to over thirty dollars. Since its acquisition of the trade name, Valeant Pharmaceuticals made little, if any, change to the pricing of Seconal. Despite the price increases implemented by Marathon Pharmaceuticals, Seconal was still manufactured by Ohm.[19] In the United States, Seconal is available only in 100 mg capsules, as asodium salt. The salt is a whitehygroscopic powder that is soluble in water and ethanol.
Whilegeneric versions of the drug were in existence after Eli Lilly's patent on Seconal expired, currently there are no companies that manufacture the drug generically in the United States. Until 2020, Valeant was the sole marketer of Seconal in the United States.[4] As of 2021, Valeant discontinued the product, and Bausch Health became the sole supplier of Seconal. Bausch Health stopped manufacturing the product in January 2022.[25]
The sodium salt of secobarbital is classified separately from the free acid, as follows:
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