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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:40:03 UTC
Update Date2021-09-14 15:47:01 UTC
HMDB IDHMDB0041803
Secondary Accession Numbers
  • HMDB41803
Metabolite Identification
Common Name2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
Description2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, also known as EDDP, is a major inactive metabolite of the opioid methadone. Methadone is an opioid drug that is often used to treat addiction to other opioids, such as heroin, oxycodone or fentanyl.​ Methadone is metabolised in the liver and small intestine where it is converted to EDDP through N-demethylation and cyclization by CYP3A4 (PMID: 15501692 , 27320437 ). EDDP and methadone are eliminated through the kidneys. As such it is common to monitor the urine of patients in a clinical and forensic settings. EDDP is formed through N-desmethylmethadone reacting with itself and cyclizing through condensation of the secondary amine with the carbonyl group (PMID: 27320437 ). EDDP belongs to the family of compounds known as Diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. EDDP is only found in individuals who have taken or been given methadone.
Structure
Data?1563863704
Synonyms
ValueSource
EDDPHMDB
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, perchlorate, (+-)-isomerHMDB
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, (e)-isomerHMDB
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, (Z)-isomerHMDB
EDDP-3,3HMDB
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, perchlorateHMDB
1,5-Dimethyl-3,3-diphenyl-2-ethylidenepyrrolidineHMDB
2-Et-1,5-dime-3,3-DPPHMDB
2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, (+-)-isomerHMDB
EDPPHMDB
Chemical FormulaC20H23N
Average Molecular Weight277.4033
Monoisotopic Molecular Weight277.183049741
IUPAC Name2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
Traditional Name2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
CAS Registry Number30223-73-5
SMILES
CC=C1N(C)C(C)CC1(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C20H23N/c1-4-19-20(15-16(2)21(19)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h4-14,16H,15H2,1-3H3
InChI KeyAJRJPORIQGYFMT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • 3-phenylpyrrolidine
  • Aralkylamine
  • N-alkylpyrrolidine
  • Pyrrole
  • Pyrrolidine
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Enamine
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID23254962
KEGG Compound IDC16659
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine
METLIN IDNot Available
PubChem Compound5378015
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. Ferrari A, Coccia CP, Bertolini A, Sternieri E: Methadone--metabolism, pharmacokinetics and interactions. Pharmacol Res. 2004 Dec;50(6):551-9. doi: 10.1016/j.phrs.2004.05.002. [PubMed:15501692 ]
  2. Dinis-Oliveira RJ: Metabolomics of methadone: clinical and forensic toxicological implications and variability of dose response. Drug Metab Rev. 2016 Nov;48(4):568-576. doi: 10.1080/03602532.2016.1192642. Epub 2016 Jun 20. [PubMed:27320437 ]