Glutethimide

Glutethimide
Clinical data
Trade names	Doriden, Elrodorm, Noxyron, others
Pregnancy; category	C: (United States);
Dependence; liability	Moderate - high
Routes of; administration	By mouth
ATC code	N05CE01 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule II; UN: Psychotropic Schedule III;
Pharmacokinetic data
Bioavailability	Variable (Tmax = 1–6 hours)
Protein binding	~50%
Metabolism	Extensive hepatic
Elimination half-life	8–12 hours
Excretion	Renal
Identifiers
	IUPAC name 3-ethyl-3-phenyl-piperidine-2,6-dione;
CAS Number	77-21-4 ;
PubChem CID	3487;
IUPHAR/BPS	7192;
DrugBank	DB01437 ;
ChemSpider	3367 ;
UNII	C8I4BVN78E;
KEGG	D00532 ;
ChEMBL	ChEMBL1102 ;
CompTox Dashboard (EPA)	DTXSID1023102 ;
ECHA InfoCard	100.000.921
Chemical and physical data
Formula	C13H15NO2
Molar mass	217.268 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	84 °C (183 °F)
Solubility in water	999 mg/L (30 °C/86 °F) mg/mL (20 °C)
	SMILES O=C1NC(CCC1(CC)C2=CC=CC=C2)=O;
	InChI InChI=1S/C13H15NO2/c1-2-13(10-6-4-3-5-7-10)9-8-11(15)14-12(13)16/h3-7H,2,8-9H2,1H3,(H,14,15,16) ; Key:JMBQKKAJIKAWKF-UHFFFAOYSA-N ;
	(verify)

Glutethimide is a hypnotic sedative that was introduced by Ciba^[3] in 1954 as a safe alternative to barbiturates to treat insomnia. Before long, however, it had become clear that glutethimide was just as likely to cause addiction and caused similar withdrawal symptoms. Doriden was the brand-name version. Current production levels in the United States (the annual quota for manufacturing imposed by the DEA has been three grams, enough for six Doriden tablets, for a number of years) point to its use only in small-scale research. Manufacturing of the drug was discontinued in the US in 1993 and discontinued in several eastern European countries in 2006.

^ 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.
^ Barceloux DG (2012). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. Hoboken, N.J.: John Wiley & Sons, Inc. pp. 492–493. ISBN 978-0-471-72760-6. OCLC 814224300.
^ US patent 2673205, Hoffmann K, Tagmann E, "3-Disubstituted Dioxopiperidines and the Manufacture thereof", issued 23 March 1954, assigned to CIBA

[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.

[2] Barceloux DG (2012). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. Hoboken, N.J.: John Wiley & Sons, Inc. pp. 492–493. ISBN 978-0-471-72760-6. OCLC 814224300.

[US2673205-3] US patent 2673205, Hoffmann K, Tagmann E, "3-Disubstituted Dioxopiperidines and the Manufacture thereof", issued 23 March 1954, assigned to CIBA

[1]

[2]

[3]

Clinical data


Trade names	Doriden, Elrodorm, Noxyron, others
Pregnancy category	C: (United States)
Dependence liability	Moderate - high
Routes of administration	By mouth
ATC code	N05CE01 (WHO)
Legal status
Legal status	AU: S8 (Controlled drug) BR: Class B1 (Psychoactive drugs)^[1] CA: Schedule IV DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule II UN: Psychotropic Schedule III
Pharmacokinetic data
Bioavailability	Variable (T_max = 1–6 hours)^[2]
Protein binding	~50%
Metabolism	Extensive hepatic
Elimination half-life	8–12 hours
Excretion	Renal
Identifiers
IUPAC name 3-ethyl-3-phenyl-piperidine-2,6-dione
CAS Number	77-21-4^Y
PubChem CID	3487
IUPHAR/BPS	7192
DrugBank	DB01437^Y
ChemSpider	3367^Y
UNII	C8I4BVN78E
KEGG	D00532^Y
ChEMBL	ChEMBL1102^Y
CompTox Dashboard (EPA)	DTXSID1023102
ECHA InfoCard	100.000.921
Chemical and physical data
Formula	C₁₃H₁₅NO₂
Molar mass	217.268 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	84 °C (183 °F)
Solubility in water	999 mg/L (30 °C/86 °F) mg/mL (20 °C)
SMILES O=C1NC(CCC1(CC)C2=CC=CC=C2)=O
InChI InChI=1S/C13H15NO2/c1-2-13(10-6-4-3-5-7-10)9-8-11(15)14-12(13)16/h3-7H,2,8-9H2,1H3,(H,14,15,16)^Y Key:JMBQKKAJIKAWKF-UHFFFAOYSA-N^Y
(verify)