Secobarbital (as the
sodium salt
Sodium salts are salt (chemistry), salts composed of a sodium cation and the conjugate base anion of some Inorganic compound, inorganic or Organic compound, organic acids. They can be formed by the Neutralization (chemistry), neutralization of su ...
, originally marketed by
Eli Lilly and Company
Eli Lilly and Company is an American pharmaceutical company headquartered in Indianapolis, Indiana, with offices in 18 countries. Its products are sold in approximately 125 countries. The company was founded in 1876 by, and named after, Colonel ...
for the treatment of insomnia, and subsequently by other companies as described below, under the brand name Seconal) is a short-acting
barbiturate
Barbiturates are a class of depressant drugs that are chemically derived from barbituric acid. They are effective when used medically as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential as we ...
derivative drug that was patented in 1934 in the United States. It possesses
anaesthetic,
anticonvulsant
Anticonvulsants (also known as antiepileptic drugs or recently as antiseizure drugs) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of b ...
,
anxiolytic,
sedative
A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are CNS depressants and interact with brain activity causing its deceleration. Various kinds of sedatives can be distinguished, but t ...
, and
hypnotic
Hypnotic (from Greek ''Hypnos'', sleep), or soporific drugs, commonly known as sleeping pills, are a class of (and umbrella term for) psychoactive drugs whose primary function is to induce sleep (or surgical anesthesiaWhen used in anesthesia ...
properties. In the United Kingdom, it was known as quinalbarbitone. It is the most frequently used drug in
physician-assisted suicide within the United States. Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill), and as a result, it has largely been replaced by the
benzodiazepine
Benzodiazepines (BZD, BDZ, BZs), sometimes called "benzos", are a class of depressant drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. They are prescribed to treat conditions such as anxiety disorders, ...
family. Seconal was widely abused, known on the street as "red devils" or "reds".
Indications
Secobarbital is indicated for:
*Treatment of
epilepsy
*Temporary treatment of
insomnia
*Use as a preoperative medication to produce
anaesthesia and
anxiolysis in short surgical, diagnostic, or therapeutic procedures which are minimally painful.
Availability
Ranbaxy Pharmaceuticals
Ranbaxy Laboratories Limited was an Indian multinational pharmaceutical company that was incorporated in India in 1961 and remained an entity until 2014. The company went public in 1973. Ownership of Ranbaxy changed twice over the course of its ...
, an India-based company now predominantly owned by the Japanese company
Daiichi Sankyo, obtained the rights to market and to use the trade name Seconal from Eli Lilly in 1998 and did so until September 18, 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, 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 to
Valeant Pharmaceuticals, 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.
In the United States, Seconal is available only in 100 mg capsules, as a
sodium salt
Sodium salts are salt (chemistry), salts composed of a sodium cation and the conjugate base anion of some Inorganic compound, inorganic or Organic compound, organic acids. They can be formed by the Neutralization (chemistry), neutralization of su ...
. The salt is a white
hygroscopic powder that is soluble in water and ethanol.
While
generic versions of the drug were in existence after Eli Lilly's patent of the name 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.
As of 2021, Valeant discontinued the product, and Bausch Health is the sole supplier of Seconal. But the product is currently experiencing a shortage and is unavailable, with no estimated date of resupply.
Secobarbital sodium
The sodium salt of secobarbital is classified separately from the free acid, as follows:
*CAS number: 309-43-3
*Chemical formula: C
12H
18N
2NaO
3
*Molecular weight: 260.265
Side effects
Possible side effects of secobarbital include:
*
Somnolence
*Impaired motor functions
** Impaired coordination
** Impaired balance (Ataxia)
**
Dizziness
*
Anxiety
*Confusion
*Agitation, irritability, or excitability
*Headache
*Hunger
*
Nausea
*Vomiting
*
Nightmares
*Increased sensitivity to pain
*
Allergic reactions
** Difficulty breathing
**
Edema
Edema, also spelled oedema, and also known as fluid retention, dropsy, hydropsy and swelling, is the build-up of fluid in the body's Tissue (biology), tissue. Most commonly, the legs or arms are affected. Symptoms may include skin which feels t ...
**
Urticaria
Withdrawal
Secobarbital may produce psychological addiction and produces physical dependence if used for an extended period of time.
Withdrawal
Withdrawal means "an act of taking out" and may refer to:
* Anchoresis (withdrawal from the world for religious or ethical reasons)
* ''Coitus interruptus'' (the withdrawal method)
* Drug withdrawal
* Social withdrawal
* Taking of money from a ban ...
symptoms may occur if long-term use is abruptly ended and can include:
*Anxiety
*Insomnia
*Lack of appetite
*Seizures
*Tremors
*Possible death as a result of withdrawal
Recreational and Lethal use
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 time
benzodiazepines
Benzodiazepines (BZD, BDZ, BZs), sometimes called "benzos", are a class of depressant drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. They are prescribed to treat conditions such as anxiety disorders, i ...
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 of
Jacqueline Susann's novel ''
Valley of the Dolls Valley of the Dolls may refer to:
* ''Valley of the Dolls'' (novel), a 1966 novel by Jacqueline Susann
** ''Valley of the Dolls'' (film), a 1967 film adapted from the novel
*** " (Theme from) Valley of the Dolls", the title song from the film, pe ...
'', whose main characters use secobarbital and other such drugs. Actresses
Carole Landis,
Judy Garland, and journalist
Dorothy Kilgallen
Dorothy Mae Kilgallen (July 3, 1913 – November 8, 1965) was an American columnist, journalist, and television game show panelist. After spending two semesters at the College of New Rochelle, she started her career shortly before her 18th birth ...
allegedly either died by suicide or of accidentally overdosing on secobarbital. Seconal was used to induce
Fred Hampton into docility before he was then executed in his bed in the early hours of December 4,1969.
In 1978, 1000 pills of Seconal were recovered in
Jonestown, along with substantial quantities of
Valium,
Thorazine,
Talwin,
Demerol
Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Eisl ...
, and other sedatives, hypnotics, and analgesics.
Use in animal and human euthanasia
In the
Netherlands, individuals have two options for
euthanasia
Euthanasia (from el, εὐθανασία 'good death': εὖ, ''eu'' 'well, good' + θάνατος, ''thanatos'' 'death') is the practice of intentionally ending life to eliminate pain and suffering.
Different countries have different eut ...
. They can orally consume 100 ml of concentrated syrup containing either 15 grams of
pentobarbital or 15 grams of secobarbital, or they can choose to have 2 grams of
thiopental
Sodium thiopental, also known as Sodium Pentothal (a trademark of Abbott Laboratories), thiopental, thiopentone, or Trapanal (also a trademark), is a rapid-onset short-acting barbiturate general anesthetic. It is the thiobarbiturate analog of pe ...
or 1 gram of
propofol
Propofol, marketed as Diprivan, among other names, is a short-acting medication that results in a decreased level of consciousness and a lack of memory for events. Its uses include the starting and maintenance of general anesthesia, sedation f ...
administered intravenously by a doctor, followed by a muscle relaxant. In recent years only 15% of those who died by euthanasia opted for orally consuming the lethal drug(s), the rest choosing to have the drugs administered intravenously by a doctor instead.
In the United States, secobarbital and pentobarbital are the most common drugs prescribed under
physician aid-in-dying laws in Oregon since 1998, Washington since 2008, and Vermont since 2013.
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.
It is a component in the
veterinary drug
Somulose, used for
euthanasia
Euthanasia (from el, εὐθανασία 'good death': εὖ, ''eu'' 'well, good' + θάνατος, ''thanatos'' 'death') is the practice of intentionally ending life to eliminate pain and suffering.
Different countries have different eut ...
of
horses and
cattle.
The of secobarbital has been reported to be between 125 mg/kg (rat, oral) and 267 mg/kg (mouse, oral).
See also
*
Tuinal
References
External links
Marathon Pharmaceuticals - SeconalFull prescribing information for the United States.
RxList.com - SecobarbitalConsumer information.
{{GABAAR PAMs
General anesthetics
Barbiturates
Eli Lilly and Company brands
Allyl compounds
GABAA receptor positive allosteric modulators