2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine (BioDeep_00000001539)

   

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, perchlorate, (+-)-isomer

化学式: C20H23N (277.183)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(otcml) 11.04%

分子结构信息

SMILES: C/C=C/1\C(CC(N1C)C)(C2=CC=CC=C2)C3=CC=CC=C3
InChI: 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

描述信息

2-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.
CONFIDENCE standard compound; EAWAG_UCHEM_ID 2825

同义名列表

13 个代谢物同义名

2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, perchlorate, (+-)-isomer; 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, (+-)-isomer; 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, perchlorate; 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, (e)-isomer; 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, (Z)-isomer; 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine; 1,5-Dimethyl-3,3-diphenyl-2-ethylidenepyrrolidine; Demethylmethadone (EDDP); 2-Et-1,5-dime-3,3-DPP; EDDP-3,3; EDPP; EDDP; 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine



数据库引用编号

30 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

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PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 8 ABCB1, CYP2A6, CYP2B6, CYP2C19, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Peripheral membrane protein 3 CYP1B1, CYP2B6, CYP2E1
Endoplasmic reticulum membrane 10 CYP19A1, CYP1A2, CYP1B1, CYP2A6, CYP2B6, CYP2C19, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Mitochondrion membrane 1 ABCG2
Nucleus 1 NR1I2
dendrite 1 OPRM1
mitochondrial membrane 1 ABCG2
nuclear body 1 NR1I2
nucleoplasm 2 ABCG2, NR1I2
Cell membrane 7 ABCB1, ABCG2, OPRM1, SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
Cell projection, axon 1 OPRM1
Multi-pass membrane protein 8 ABCB1, ABCG2, CYP19A1, OPRM1, SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
Synapse 1 OPRM1
cell surface 1 ABCB1
Golgi apparatus 1 OPRM1
mitochondrial inner membrane 1 CYP2E1
Lysosome 1 SGSH
endosome 1 OPRM1
plasma membrane 9 ABCB1, ABCG2, CYP2C19, CYP2C9, OPRM1, SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
Membrane 12 ABCB1, ABCG2, CYP19A1, CYP1B1, CYP2A6, CYP2D6, CYP3A4, OPRM1, SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
apical plasma membrane 4 ABCB1, ABCG2, SLCO1A2, SLCO2B1
axon 1 OPRM1
basolateral plasma membrane 4 SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
extracellular exosome 2 ABCB1, SGSH
endoplasmic reticulum 3 CYP19A1, CYP2D6, OPRM1
lysosomal lumen 1 SGSH
mitochondrion 2 CYP1B1, CYP2D6
intracellular membrane-bounded organelle 9 CYP1A2, CYP1B1, CYP2A6, CYP2B6, CYP2C19, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Microsome membrane 8 CYP19A1, CYP1A2, CYP1B1, CYP2B6, CYP2C9, CYP2D6, CYP2E1, CYP3A4
Single-pass membrane protein 1 CYP2D6
transcription regulator complex 1 NR1I2
perikaryon 1 OPRM1
Apical cell membrane 3 ABCB1, ABCG2, SLCO2B1
Mitochondrion inner membrane 1 CYP2E1
Membrane raft 1 ABCG2
neuron projection 1 OPRM1
chromatin 1 NR1I2
brush border membrane 1 ABCG2
Basolateral cell membrane 3 SLCO1B1, SLCO1B3, SLCO2B1
Cell projection, dendrite 1 OPRM1
intermediate filament cytoskeleton 1 NR1I2
basal plasma membrane 4 SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
cytoplasmic microtubule 1 CYP2A6
Basal cell membrane 4 SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
external side of apical plasma membrane 2 ABCB1, ABCG2
[Isoform 12]: Cytoplasm 1 OPRM1


文献列表

  • Katharina Feld, Patrick Dahm, Tobias Kieliba, Axel Klee, Markus A Rothschild, Hilke Andresen-Streichert, Justus Beike. Evidence for the transfer of methadone and EDDP by sweat to children's hair. International journal of legal medicine. 2021 Sep; 135(5):1799-1811. doi: 10.1007/s00414-021-02576-1. [PMID: 33821333]
  • Mohamed Abou El Hassan, David Colantonio, Sergei Likhodii, Bassam A Nassar. The analytical performance of six urine drug screens on cobas 6000 and ARCHITECT i2000 compared to LC-MS/MS gold standard. Clinical biochemistry. 2021 Jul; 93(?):99-103. doi: 10.1016/j.clinbiochem.2021.04.003. [PMID: 33844982]
  • Ingrid F Metzger, Anna E Thomas, Cindy A Evrard, David R Jones, Andrea R Masters, David M Haas, Laura S Haneline, Sara K Quinney. Stereoselective Analysis of Methadone and EDDP in Laboring Women and Neonates in Plasma and Dried Blood Spots and Association with Neonatal Abstinence Syndrome. American journal of perinatology. 2021 07; 38(9):968-975. doi: 10.1055/s-0040-1701505. [PMID: 32052397]
  • Karolina Nowak, Paweł Szpot, Tomasz Jurek, Marcin Zawadzki. Quantification of methadone and its metabolites: EDDP and EMDP determined in autopsy cases using LC-MS/MS. Journal of forensic sciences. 2021 May; 66(3):1003-1012. doi: 10.1111/1556-4029.14674. [PMID: 33512019]
  • Dheepthi Arakonam Ravishankar, Erin Calhoun, Roopa Sethi, Amad Din. Urine toxicology screen negative for Methadone metabolite but positive for Methadone in a patient on Methadone maintenance therapy (MMT). Asian journal of psychiatry. 2020 Apr; 50(?):101969. doi: 10.1016/j.ajp.2020.101969. [PMID: 32109808]
  • Regula Theurillat, Friederike A Sandbaumhüter, Claudia Gittel, M Paula Larenza Menzies, Christina Braun, Wolfgang Thormann. Enantioselective capillary electrophoresis for pharmacokinetic analysis of methadone and 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine in equines anesthetized with ketamine and isoflurane. Electrophoresis. 2019 08; 40(15):1959-1965. doi: 10.1002/elps.201900044. [PMID: 30900259]
  • Željko Ključević, Benjamin Benzon, Nikola Ključević, Maja Veršić Bratinčević, Davorka Sutlović. Liver damage indices as a tool for modifying methadone maintenance treatment: a cross-sectional study. Croatian medical journal. 2018 Dec; 59(6):298-306. doi: . [PMID: 30610772]
  • Lana Brockbals, Sandra N Staeheli, Dominic Gascho, Lars C Ebert, Thomas Kraemer, Andrea E Steuer. Time-Dependent Postmortem Redistribution of Opioids in Blood and Alternative Matrices. Journal of analytical toxicology. 2018 Jul; 42(6):365-374. doi: 10.1093/jat/bky017. [PMID: 29579266]
  • Taryn M Guinan, Declan Neldner, Peter Stockham, Hilton Kobus, Christopher B Della Vedova, Nicolas H Voelcker. Porous silicon mass spectrometry as an alternative confirmatory assay for compliance testing of methadone. Drug testing and analysis. 2017 May; 9(5):769-777. doi: 10.1002/dta.2033. [PMID: 27364015]
  • Nicola Mastroianni, Maria Jose Bleda, Miren López de Alda, Damià Barceló. Occurrence of drugs of abuse in surface water from four Spanish river basins: Spatial and temporal variations and environmental risk assessment. Journal of hazardous materials. 2016 10; 316(?):134-42. doi: 10.1016/j.jhazmat.2016.05.025. [PMID: 27232724]
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