Glutethimide

Glutethimide
Glutethimide
Systematic (IUPAC) name
3-ethyl-3-phenyl-piperidine-2,6-dione
Clinical data
Pregnancy cat. C: (United States)
Legal status Schedule II (US)
Schedule III international
Routes oral
Pharmacokinetic data
Bioavailability Variable
Metabolism Hepatic
Half-life 10-12 hours
Excretion Renal:2% Fecal:2%
Identifiers
CAS number 77-21-4 YesY
ATC code N05CE01
PubChem CID 3487
DrugBank DB01437
ChemSpider 3367 YesY
UNII C8I4BVN78E YesY
KEGG D00532 YesY
ChEMBL CHEMBL1102 YesY
Chemical data
Formula C13H15NO2 
Mol. mass 217.264 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Glutethimide is a hypnotic sedative that was introduced 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 similarly severe withdrawal symptoms. Doriden is the brand-name version of the drug; both the generic and brand-name forms are rarely prescribed today.

Glutethimide DOJ.jpg

Contents

Long term use

In long term use rebound effects , which resembled those seen in withdrawal, have anecdotally been described in patients, who were still taking a stable dose of the drug. The symptoms included delirium, hallucinosis, convulsions and fever.[1]

Recreational use

Glutethimide is a CYP2D6 enzyme inducer. When taken with codeine, it enables the body to convert higher amounts of the codeine (higher than the average 5 - 10%) to morphine. The general sedative effect also adds to the effect of the combination.[2][3]

Legal status

Glutethimide is a Schedule II drug under the Convention on Psychotropic Substances.[4] It was originally a Schedule III drug in the United States under the Controlled Substances Act, but in 1991 it was upgraded to Schedule II[5], after it was discovered that misuse combined with codeine increased the effect of the codeine and deaths had resulted from the combination.[6][7]

Chemistry

Glutethimide (2-ethyl-2-phenylgutarimide) is synthesized by addition of 2-phenylbutyronitrile to the methylacrylate (Michael reaction), and the subsequent alkaline hydrolysis of the nitrile group in the obtained compound into an amide group, and the subsequent acidic cyclization of the product into the desired glutethimide.[8]

Glutethimide syn.png

See also

References

  1. ^ Cookson, J. C. (1995). "Rebound exacerbation of anxiety during prolonged tranquilizer ingestion". Journal of the Royal Society of Medicine 88 (9): 544. PMC 1295346. PMID 7562864. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1295346.  edit
  2. ^ Popa, D.; Loghin, F.; Imre, S.; Curea, E. (2003). "The study of codeine-gluthetimide pharmacokinetic interaction in rats". Journal of pharmaceutical and biomedical analysis 32 (4–5): 867–877. PMID 12899973.  edit
  3. ^ Khajawall, A. M.; Sramek Jr, J. J.; Simpson, G. M. (1982). "'Loads' Alert". The Western journal of medicine 137 (2): 166–168. PMC 1274052. PMID 7135952. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1274052.  edit
  4. ^ "List of psychotropic substances under international control" (pdf). INCB. http://www.incb.org/pdf/e/list/green.pdf. 
  5. ^ "Code of Federal Regulations Section 1308.12 Schedule II". DEA. http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_12.htm. 
  6. ^ Havier, R. G.; Lin, R. (1985). "Deaths as a result of a combination of codeine and glutethimide". Journal of forensic sciences 30 (2): 563–566. PMID 3998703.  edit
  7. ^ Feuer, E.; French, J. (1984). "Descriptive epidemiology of mortality in New Jersey due to combinations of codeine and glutethimide". American journal of epidemiology 119 (2): 202–207. PMID 6695899.  edit
  8. ^ Tagmann, E.; Sury, E.; Hoffmann, K. (1952). "Über Alkylenimin-Derivate. 2. Mitteilung". Helvetica Chimica Acta 35: 1541–1548. doi:10.1002/hlca.19520350516.  edit
    DE patent 950193, Hoffmann,K. & Tagmann,E., "Verfahren zur Herstellung neuer Dioxopiperidine" 
    US patent 2673205, Hoffmann,K. & Tagmann,E., "3-disubstituted dioxopiperidines and the manufacture thereof" 
    F. Salmon-Legagneur, C. Neveu, Compt. Rend., 234, 1060 (1952).
    F. Salmon-Legagneur, C. Neveu, Bull. Soc. Chim. France, 70 (1953).

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Look at other dictionaries:

  • glutethimide — noun Etymology: gluten + eth + imide Date: 1955 a sedative hypnotic drug C13H15NO2 that is a derivative of piperidine and has pharmacological properties similar to those of barbiturates …   New Collegiate Dictionary

  • glutethimide — /glooh teth euh muyd /, n. Pharm. a white, crystalline, water insoluble powder, C13H15NO2, used as a hypnotic and sedative. [1950 55; GLUTE(N) + THI + (A)MIDE] * * * …   Universalium

  • glutethimide — noun A hypnotic sedative formerly used as an alternative to barbiturates to treat insomnia …   Wiktionary

  • glutethimide — A central nervous system depressant used as a hypnotic in simple insomnia and formerly as a daytime sedative. * * * glu·teth·i·mide glü teth ə .mīd, məd n a sedative hypnotic drug C13H15NO2 that is a derivative of piperidine and has… …   Medical dictionary

  • glutethimide — n. chemical substance used as a sedative and hypnotic drug …   English contemporary dictionary

  • glutethimide — glu·teth·i·mide …   English syllables

  • glutethimide — noun sedative (trade name Doriden) used to treat some sleep disorders • Syn: ↑Doriden • Usage Domain: ↑trade name (for: ↑Doriden) • Hypernyms: ↑sedative, ↑ …   Useful english dictionary

  • Propofol — Systematic (IUPAC) name 2,6 diisopropylphenol …   Wikipedia

  • Gamma-Hydroxybutyric acid — γ Hydroxybutyric acid Systematic (IUPAC) name 4 Hydroxybutanoic acid …   Wikipedia

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