Pentobarbital

Pentobarbital
	Above: molecular structure of pentobarbitone (keto form) Below: 3D representation of pentobarbitone (keto form) molecule
Clinical data
Trade names	Nembutal
AHFS/Drugs.com	Monograph
MedlinePlus	a682416
License data	US DailyMed: Pentobarbital;
Pregnancy; category	AU: C;
Routes of; administration	By mouth, intravenous, intramuscular, rectal
Drug class	Barbiturate
ATC code	N05CA01 (WHO) QN51AA01 (WHO);
Legal status
Legal status	AU: S8 (Controlled drug) , S4 for IV preparations; BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Anlage III (Special prescription form required); UK: Class B; US: Schedule II; UN: Psychotropic Schedule III; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	70–90% (oral); 90% (rectal)
Protein binding	20–45%
Metabolism	Liver
Elimination half-life	15–48 hours
Excretion	Kidney
Identifiers
	IUPAC name 5-Ethyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione;
CAS Number	76-74-4 ;
PubChem CID	4737;
IUPHAR/BPS	5480;
DrugBank	DB00312 ;
ChemSpider	4575 ;
UNII	I4744080IR;
KEGG	D00499 ;
ChEBI	CHEBI:7983 ;
ChEMBL	ChEMBL448 ;
CompTox Dashboard (EPA)	DTXSID7023435 ;
ECHA InfoCard	100.000.895
Chemical and physical data
Formula	C11H18N2O3
Molar mass	226.276 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1NC(=O)NC(=O)C1(C(C)CCC)CC;
	InChI InChI=1S/C11H18N2O3/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16) ; Key:WEXRUCMBJFQVBZ-UHFFFAOYSA-N ;
	(verify)

Pentobarbital (US) or pentobarbitone (British and Australian) is a short-acting barbiturate typically used as a sedative, a preanesthetic, and to control convulsions in emergencies.^[3] It can also be used for short-term treatment of insomnia but has been largely replaced by the benzodiazepine family of drugs.

In high doses, pentobarbital causes death by respiratory arrest. It is used for veterinary euthanasia and is used by some US states and the United States federal government for executions of convicted criminals by lethal injection.^[4] In some countries and states, it is also used for physician-assisted suicide.^[5]^[6]

Pentobarbital was widely abused beginning in the late 1930s and sometimes known as "yellow jackets" due to the yellow color of Nembutal-branded capsules.^[7]

Pentobarbital was developed by Ernest H. Volwiler and Donalee L. Tabern at Abbott Laboratories in 1930.

^ "Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024". 30 May 2024.
^ Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
^ Cite error: The named reference :0 was invoked but never defined (see the help page).
^ Palmer K (28 October 2013). "Ohio says it will switch to new drugs for executions". Reuters.
^ Cite error: The named reference ABC was invoked but never defined (see the help page).
^ Cite error: The named reference Stuff was invoked but never defined (see the help page).
^ Cozanitis, Dimitri A (December 2004). "One hundred years of barbiturates and their saint". Journal of the Royal Society of Medicine. 97 (12): 594–598. doi:10.1177/014107680409701214. ISSN 0141-0768. PMC 1079678. PMID 15574863.

[1] "Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024". 30 May 2024.

[2] Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

[:0-3] Cite error: The named reference :0 was invoked but never defined (see the help page).

[auto-4] Palmer K (28 October 2013). "Ohio says it will switch to new drugs for executions". Reuters.

[ABC-5] Cite error: The named reference ABC was invoked but never defined (see the help page).

[Stuff-6] Cite error: The named reference Stuff was invoked but never defined (see the help page).

[7] Cozanitis, Dimitri A (December 2004). "One hundred years of barbiturates and their saint". Journal of the Royal Society of Medicine. 97 (12): 594–598. doi:10.1177/014107680409701214. ISSN 0141-0768. PMC 1079678. PMID 15574863.

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