Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 15:44:52 UTC
HMDB IDHMDB0015505
Secondary Accession Numbers
  • HMDB15505
Metabolite Identification
Common NameGlutethimide
DescriptionGlutethimide, also known as doriden or noxiron, belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group. Doriden was the brand-name version. Glutethimide is a drug which is used for the treatment of insomnia. The effect was also used clinically, including some research in the 1970s in various countries of using it under carefully monitored circumstances as a form of oral opioid agonist substitution therapy, e.g. as a Substitutionmittel that may be a useful alternative to methadone. Glutethimide is an extremely weak basic (essentially neutral) compound (based on its pKa). Glutethimide is a potentially toxic compound. Glutethimide (3-ethyl-3-phenylgutarimide) is synthesized by addition of 2-phenylbutanenitrile 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. Production of glutethimide was discontinued in the US in 1993 and in several eastern European countries, most notably Hungary, in 2006. Glutethimide is a hypnotic sedative that was introduced by Ciba in 1954 as a safe alternative to barbiturates to treat insomnia. The general sedative effect of the glutethimide also adds to the effect of the combination. 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, several years after it was discovered that misuse combined with codeine increased the effect of the codeine and deaths had resulted from the combination. It produces an intense, long lasting euphoria similar to IV heroin use.
Structure
Data?1582753304
Synonyms
ValueSource
2-Ethyl-2-phenylglutarimideKegg
DoridenKegg
GlutathimidHMDB
GlutethimidHMDB
GlutetimidHMDB
GlutetimideHMDB
GluthetimideHMDB
NoxironHMDB
Chemical FormulaC13H15NO2
Average Molecular Weight217.2637
Monoisotopic Molecular Weight217.110278729
IUPAC Name3-ethyl-3-phenylpiperidine-2,6-dione
Traditional Nameglutethimide
CAS Registry Number77-21-4
SMILES
CCC1(CCC(=O)NC1=O)C1=CC=CC=C1
InChI Identifier
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)
InChI KeyJMBQKKAJIKAWKF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPhenylpiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • Piperidinedione
  • Delta-lactam
  • Piperidinone
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid imide
  • Dicarboximide
  • Carboxylic acid imide, n-unsubstituted
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point84 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.33 g/LNot Available
LogP1.90HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP10(1.89) g/LALOGPS
logP10(2.13) g/LChemAxon
logS10(-2.8) g/LALOGPS
pKa (Strongest Acidic)11.69ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.17 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.65 m³·mol⁻¹ChemAxon
Polarizability23.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.27231661259
DarkChem[M-H]-149.87431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlutethimideCCC1(CCC(=O)NC1=O)C1=CC=CC=C13050.8Standard polar33892256
GlutethimideCCC1(CCC(=O)NC1=O)C1=CC=CC=C11865.3Standard non polar33892256
GlutethimideCCC1(CCC(=O)NC1=O)C1=CC=CC=C11834.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glutethimide,1TMS,isomer #1CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C)C1=O1785.1Semi standard non polar33892256
Glutethimide,1TMS,isomer #1CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C)C1=O1943.4Standard non polar33892256
Glutethimide,1TMS,isomer #1CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C)C1=O2347.7Standard polar33892256
Glutethimide,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O2034.3Semi standard non polar33892256
Glutethimide,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O2225.0Standard non polar33892256
Glutethimide,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O2452.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Glutethimide CI-B (Non-derivatized)splash10-014i-0090000000-df13dd29711d257fd7b02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glutethimide EI-B (Non-derivatized)splash10-014r-4900000000-8d3add816c0b57475d492017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glutethimide CI-B (Non-derivatized)splash10-014i-0090000000-df13dd29711d257fd7b02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glutethimide EI-B (Non-derivatized)splash10-014r-4900000000-8d3add816c0b57475d492018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glutethimide GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0910000000-d4d4c3a1f5db854968c02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glutethimide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glutethimide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 10V, Positive-QTOFsplash10-014i-0190000000-72b760efeea835d3cf1e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 20V, Positive-QTOFsplash10-014i-0970000000-0603b8569eb1b10cffbe2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 40V, Positive-QTOFsplash10-014l-7900000000-7cca93b10fbffd2523fb2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 10V, Negative-QTOFsplash10-014i-0190000000-034582ee53afcabdc9bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 20V, Negative-QTOFsplash10-014i-2690000000-bc585fc480978eb7f6cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 40V, Negative-QTOFsplash10-0006-9500000000-be385f1bbd1a5d15aaac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 10V, Positive-QTOFsplash10-014i-0090000000-d93a386fc7fe30c047682021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 20V, Positive-QTOFsplash10-015a-1920000000-4a4e8b58a6f95e617b7a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 40V, Positive-QTOFsplash10-016x-4900000000-d532a9a5e733836613dd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 10V, Negative-QTOFsplash10-014i-0090000000-60f515abe6e3ab4eefc12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 20V, Negative-QTOFsplash10-0006-9120000000-4eac9851d466e1aae06a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glutethimide 40V, Negative-QTOFsplash10-0006-9300000000-d1955b8d3cf771a3f9af2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01437 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01437 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01437
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3367
KEGG Compound IDC07489
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlutethimide
METLIN IDNot Available
PubChem Compound3487
PDB IDNot Available
ChEBI ID251300
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular weight:
60101.87
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Pearson MW, Roberts CJ: Drug induction of hepatic enzymes in the elderly. Age Ageing. 1984 Sep;13(5):313-6. [PubMed:6496244 ]
  2. Petik D, Acs N, Banhidy F, Czeizel AE: A study of the effects of large doses of glutethimide that were used for self-poisoning during pregnancy on human fetuses. Toxicol Ind Health. 2008 Feb-Mar;24(1-2):69-78. doi: 10.1177/0748233708089014. [PubMed:18818183 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
References
  1. Skerritt JH, Johnston GA: Interactions of some anaesthetic, convulsant, and anticonvulsant drugs at GABA-benzodiazepine receptor-ionophore complexes in rat brain synaptosomal membranes. Neurochem Res. 1983 Oct;8(10):1351-62. [PubMed:6318143 ]