Secobarbital

Secobarbital
Clinical data
Trade names	Seconal, others
Other names	Quinalbarbitone
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a682386
Pregnancy; category	D (United States);
Routes of; administration	By mouth, intravenous
Drug class	Barbiturate
ATC code	N05CA06 (WHO) QN51AA02 (WHO);
Legal status
Legal status	BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Anlage III (Special prescription form required); UK: Class B; US: Schedule II except when combined in a dosage unit with another active drug (in which case Schedule III); UN: Psychotropic Schedule II;
Pharmacokinetic data
Bioavailability	?
Protein binding	45-60%
Metabolism	Hepatic
Elimination half-life	15-40 hours
Excretion	Renal
Identifiers
	IUPAC name (RS)-5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione;
CAS Number	76-73-3 ;
PubChem CID	5193;
IUPHAR/BPS	7615;
DrugBank	DB00418 ;
ChemSpider	5005 ;
UNII	1P7H87IN75;
KEGG	D00430 ;
ChEBI	CHEBI:9073 ;
ChEMBL	ChEMBL447 ;
CompTox Dashboard (EPA)	DTXSID6044145 ;
ECHA InfoCard	100.000.894
Chemical and physical data
Formula	C12H18N2O3
Molar mass	238.287 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1NC(NC(C1(CC=C)C(CCC)C)=O)=O;
	InChI InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17) ; Key:KQPKPCNLIDLUMF-UHFFFAOYSA-N ;
	(verify)

Secobarbital, sold under the brand name Seconal among others, is a short-acting barbiturate drug originally used for the treatment of insomnia. It was patented by Eli Lilly and Company in 1934 in the United States.^[3] It possesses anesthetic, anticonvulsant, anxiolytic, sedative, and hypnotic properties. In the United Kingdom, it was known as quinalbarbitone. Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill) and has largely been replaced by the benzodiazepine family. It was widely abused, known on the street as "red devils" or "reds."^[4] Among barbiturates, secobarbital carries a particularly high risk of abuse and addiction, which is largely responsible for it falling out of use.

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b Lexi-Comp. "Secobarbital". Archived from the original on 2007-12-02.
^ US patent 1954429, Shonle HA, "Propyl-Methyl Carbinyl Allyl Barbituric Acid and its Salts", issued 1934-04-10, assigned to Eli Lilly
^ Dembosky A (23 March 2016). "Drug Company Jacks Up Cost Of Aid-In-Dying Medication". NPR. Archived from the original on 2016-03-23. Retrieved 2016-03-24.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[merck-2] Lexi-Comp. "Secobarbital". Archived from the original on 2007-12-02.

[3] US patent 1954429, Shonle HA, "Propyl-Methyl Carbinyl Allyl Barbituric Acid and its Salts", issued 1934-04-10, assigned to Eli Lilly

[:0-4] Dembosky A (23 March 2016). "Drug Company Jacks Up Cost Of Aid-In-Dying Medication". NPR. Archived from the original on 2016-03-23. Retrieved 2016-03-24.

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