Secobarbital

Structural formula
Structural formula without stereochemistry
General
Non-proprietary name	Secobarbital
other names	5- (1-methylbutyl) -5- (2-propenyl) - (1 H , 3 H , 5 H ) -pyrimidine-2,4,6-trione
Molecular formula	C 12 H 18 N 2 O 3
External identifiers / databases
CAS number 76-73-3 309-43-3 ( monosodium salt ) EC number 200-982-2 ECHA InfoCard 100,000,894 PubChem 5193 ChemSpider 5005 DrugBank DB00418 Wikidata Q414788
Drug information
ATC code	N05 CA06
Drug class	barbiturate
properties
Molar mass	238.28 g mol −1
Physical state	firmly
Melting point	100 ° C
pK s value	pK s1 = 7.2 pK s2 = 12.6
solubility	bad in water
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances danger H and P phrases H: 301-315-319-335 P: 261-301 + 310-305 + 351 + 338
Toxicological data	80 mg kg −1 ( LD 50 ,  rat ,  iv ) 145 mg kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Secobarbital is a sleep aid belonging to the group of barbiturates , more precisely: a short-acting oxybarbiturate.

effect

The effect is dose-dependent narcotic, calming, anxiolytic, antispasmodic, respiratory depressant and hypotensive. It is based on an increase in the response of the GABA receptors on inhibitory neurons in the brain (GABA = γ-aminobutyric acid , a neurotransmitter ). Common side effects are fatigue, confusion, headache, stomach pain, and paradoxical excitement. Because of the high potential for addiction (habituation, physical dependence, withdrawal symptoms) and the risk of serious side effects up to fatal respiratory arrest, the barbiturates are only rarely used in medicine; They have been replaced by benzodiazepines , especially as sleeping pills . Nevertheless, they are issued (albeit reluctantly and rarely) to patients with severe sleep disorders (chronic insomnia ). The reason for this is that the effect is not only sleep-inducing, but compelling sleep ( narcotic ).

Secobarbital's monosodium salt is a water-soluble powder or tablet with a slightly bitter taste. The effect only lasts for about 1–2 hours. Secobarbital is metabolized in the liver and the degradation products are excreted in the urine.

hazards

The use of this drug in combination with excessive alcohol consumption led in most cases to ventricular fibrillation or fatal respiratory arrest, so it is generally not recommended.

A well-known victim of a fatal secobarbital overdose is Judy Garland , who died on June 22, 1969, twelve days after her 47th birthday, from an accidentally ingested overdose of ten capsules of Secobarbital.

Legal status

Secobarbital is no longer available as a finished medicinal product in Europe. In the USA it is sold under the trade name Seconal . Real and counterfeit tablets (“Seggies”) are traded illegally on the black market.

Secobarbital is a marketable and prescription narcotic drug in the Federal Republic of Germany due to its listing in Appendix 3 BtMG. Handling without permission or prescription is generally punishable. Further information can be found in the main article Narcotics Law in Germany .

Similar regulations apply in Switzerland.

Individual evidence

1. ↑ ^{a b c d} Entry on Secobarbital. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
2. ↑ ^{a b c d} data sheet Secobarbital from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !