3,4-Dimethoxyphenylethylamine (BioDeep_00000017885)

   

human metabolite Endogenous


代谢物信息卡片


2-(3,4-Dimethoxyphenyl)ethanamine (acd/name 4.0)

化学式: C10H15NO2 (181.110273)
中文名称: 3,4-二甲氧基苯乙胺
谱图信息: 最多检出来源 Bos taurus(endogenous) 3.7%

分子结构信息

SMILES: c1(c(ccc(c1)CCN)OC)OC
InChI: InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3

描述信息

3,4-Dimethoxyphenylethylamine, also known as 3,4-DMPEA or DMPEA is an endogenous metabolite found in urine that belongs to both the phenethylamine and catecholamine families. DMPEA is an analogue of dopamine (3,4-dihydroxyphenethylamine), with a substitution of the hydroxy groups with methoxy groups. DMPEA is also structurally similar to mescaline (3,4,5-trimethoxyphenylethylamine) and occurs naturally alongside it in various species of cacti such as the San Pedro and Peruvian Torch (PMID: 5511715, 925910, 600028). DMPEA received wide attention after it was proposed as a biomarker in schizophrenic patients urine, however later studies revealed that DMPEA is also excreted by non-schizophrenics (PMID: 709888). DMPEA has little known bioactivity, but it has some action as a monoamine oxidase inhibitor (PMID: 886445). DMPEA has also been shown to have neurotoxic effects, especially in the nigrostriatal system and among dopaminergic neurons (PMID: 9409711, 9134983). DMPEA appears to be an inhibitor of mitochondrial complex I (PMID: 9409711).

同义名列表

38 个代谢物同义名

2-(3,4-Dimethoxyphenyl)ethanamine (acd/name 4.0); 2-(3,4-Dimethoxyphenyl)ethylamine (acd/name 4.0); beta-(3,4-Dimethyoxyphenyl)ethylamine; 2-(3,4-dimethoxyphenyl)ethan-1-amine; beta-(3,4-Dimethoxyphenyl)ethylamine; 3, 4-Dimethoxy-beta-phenylethylamine; 3, 4-Dimethoxyphenylethylamine(base); 3,4-Dimethoxy-beta-phenylethylamine; 2-(3,4-Dimethoxy-phenyl)-ethylamine; 3,4-Dimethoxyphenylethylamine(base); b-(3,4-Dimethyoxyphenyl)ethylamine; Β-(3,4-dimethyoxyphenyl)ethylamine; 3, 4-Dimethoxy-beta-phenethylamine; 2-(3,4-Dimethoxyphenyl)ethanamine; 2-(3,4-Dimethoxyphenyl)ethylamine; 3,4-Dimethoxy-beta-phenethylamine; 3,4-Dimethoxy-b-phenylethylamine; 3,4-Dimethoxy-β-phenylethylamine; 3,4-Dimethoxy-benzeneethanamine; 3, 4-Dimethoxybenzeneethanamine; 3,4-Dimethoxy-benzenethanamine; 3,4-Dimethoxybenzeneethanamine; 3,4-Dimethoxyphenylethylamine; 3,4-Dimethoxypheneethylamine; 3, 4-Dimethoxyphenethylamine; 3,4-Dimethoxy-phenethylamine; 3,4-Dimethoxyphenethylamine; Dimethoxyphenylethylamine; Dopamine dimethyl ether; 3,4-Di-O-methyldopamine; 3,4-Dimethoxydopamine; O,O-Dimethyldopamine; Dimethylmescaline; Homoveratrylamine; Dimethoxydopamine; DIMPEA; DMPEA; DMPE



数据库引用编号

12 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)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

4 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。



文献列表

  • Kyung Sik Yoon, Sun Mi Gu, Hye Jin Cha, Young-Hoon Kim, Jaesuk Yun, Jin-Moo Lee. 25I-NBOMe, a phenethylamine derivative, induces adverse cardiovascular effects in rodents: possible involvement of p21 (CDC42/RAC)-activated kinase 1. Drug and chemical toxicology. 2022 Mar; 45(2):898-906. doi: 10.1080/01480545.2020.1784924. [PMID: 32597268]
  • Katarzyna Kamińska, Paweł Świt, Kamilla Malek. 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOME): A Harmful Hallucinogen Review. Journal of analytical toxicology. 2021 Jan; 44(9):947-956. doi: 10.1093/jat/bkaa022. [PMID: 32128596]
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  • Elias Lützen, Michael Holtkamp, Imke Stamme, Robin Schmid, Michael Sperling, Michael Pütz, Uwe Karst. Multimodal imaging of hallucinogens 25C- and 25I-NBOMe on blotter papers. Drug testing and analysis. 2020 Apr; 12(4):465-471. doi: 10.1002/dta.2751. [PMID: 31846172]
  • Anna Šuláková, Lucie Fojtíková, Barbora Holubová, Kateřina Bártová, Oldřich Lapčík, Martin Kuchař. Two immunoassays for the detection of 2C-B and related hallucinogenic phenethylamines. Journal of pharmacological and toxicological methods. 2019 Jan; 95(?):36-46. doi: 10.1016/j.vascn.2018.11.001. [PMID: 30481558]
  • Jaya Prabhakaran, Christine DeLorenzo, Francesca Zanderigo, Gitte M Knudsen, Nic Gilling, Mali Pratap, Matthew J Jorgensen, James Daunais, Jay R Kaplan, Ramin V Parsey, J John Mann, Dileep Kumar. In vivo PET Imaging of [11C]CIMBI-5, a 5-HT2AR Agonist Radiotracer in Nonhuman Primates. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2019; 22(1):352-364. doi: 10.18433/jpps30329. [PMID: 31356761]
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  • Michelle Williams, Jennifer Martin, Peter Galettis. A Validated Method for the Detection of 32 Bath Salts in Oral Fluid. Journal of analytical toxicology. 2017 Oct; 41(8):659-669. doi: 10.1093/jat/bkx055. [PMID: 28985394]
  • Maren Hermanns-Clausen, Verena Angerer, Josephine Kithinji, Christina Grumann, Volker Auwärter. Bad trip due to 25I-NBOMe: a case report from the EU project SPICE II plus. Clinical toxicology (Philadelphia, Pa.). 2017 Sep; 55(8):922-924. doi: 10.1080/15563650.2017.1319572. [PMID: 28471280]
  • Lorna A Nisbet, Rafael Venson, Fiona M Wylie, Karen S Scott. Application of a Urine and Hair Validated LC-MS-MS Method to Determine the Effect of Hair Color on the Incorporation of 25B-NBOMe, 25C-NBOMe and 25I-NBOMe into Hair in the Rat. Journal of analytical toxicology. 2017 Jul; 41(6):559-565. doi: 10.1093/jat/bkx053. [PMID: 28830123]
  • Ariane Wohlfarth, Markus Roman, Mikael Andersson, Fredrik C Kugelberg, Xingxing Diao, Jeremy Carlier, Caroline Eriksson, Xiongyu Wu, Peter Konradsson, Martin Josefsson, Marilyn A Huestis, Robert Kronstrand. 25C-NBOMe and 25I-NBOMe metabolite studies in human hepatocytes, in vivo mouse and human urine with high-resolution mass spectrometry. Drug testing and analysis. 2017 May; 9(5):680-698. doi: 10.1002/dta.2044. [PMID: 27448631]
  • Tatsuyuki Kanamori, Tadashi Yamamuro, Kenji Kuwayama, Kenji Tsujikawa, Yuko T Iwata, Hiroyuki Inoue. Synthesis and Analysis of Glucuronic Acid-Conjugated Metabolites of 4-Bromo-2,5-Dimethoxyphenethylamine. Journal of forensic sciences. 2017 Mar; 62(2):488-492. doi: 10.1111/1556-4029.13266. [PMID: 27874182]
  • Paul Gee, Leo J Schep, Berit P Jensen, Grant Moore, Stuart Barrington. Case series: toxicity from 25B-NBOMe--a cluster of N-bomb cases. Clinical toxicology (Philadelphia, Pa.). 2016; 54(2):141-6. doi: 10.3109/15563650.2015.1115056. [PMID: 26621342]
  • Justin L Poklis, Carl E Wolf, Carrol R Nanco, Alphonse Poklis. Recommendations for specimen collection for NBOMe analysis in clinical toxicology. Clinical toxicology (Philadelphia, Pa.). 2016; 54(2):161-2. doi: 10.3109/15563650.2015.1118489. [PMID: 26696362]
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  • Kevin G Shanks, Thomas Sozio, George S Behonick. Fatal Intoxications with 25B-NBOMe and 25I-NBOMe in Indiana During 2014. Journal of analytical toxicology. 2015 Oct; 39(8):602-6. doi: 10.1093/jat/bkv058. [PMID: 26378133]
  • Lyndsey M Lowe, Brianna L Peterson, Fiona J Couper. A Case Review of the First Analytically Confirmed 25I-NBOMe-Related Death in Washington State. Journal of analytical toxicology. 2015 Oct; 39(8):668-71. doi: 10.1093/jat/bkv092. [PMID: 26378143]
  • Justin L Poklis, Sara K Dempsey, Kai Liu, Joseph K Ritter, Carl Wolf, Shijun Zhang, Alphonse Poklis. Identification of Metabolite Biomarkers of the Designer Hallucinogen 25I-NBOMe in Mouse Hepatic Microsomal Preparations and Human Urine Samples Associated with Clinical Intoxication. Journal of analytical toxicology. 2015 Oct; 39(8):607-16. doi: 10.1093/jat/bkv079. [PMID: 26378134]
  • Achim T Caspar, Andreas G Helfer, Julian A Michely, Volker Auwärter, Simon D Brandt, Markus R Meyer, Hans H Maurer. Studies on the metabolism and toxicological detection of the new psychoactive designer drug 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOMe) in human and rat urine using GC-MS, LC-MS(n), and LC-HR-MS/MS. Analytical and bioanalytical chemistry. 2015 Sep; 407(22):6697-719. doi: 10.1007/s00216-015-8828-6. [PMID: 26108532]
  • Larissa K Laskowski, Faesal Elbakoush, Jessica Calvo, Gina Exantus-Bernard, Jane Fong, Justin L Poklis, Alphonse Poklis, Lewis S Nelson. Evolution of the NBOMes: 25C- and 25B- Sold as 25I-NBOMe. Journal of medical toxicology : official journal of the American College of Medical Toxicology. 2015 Jun; 11(2):237-41. doi: 10.1007/s13181-014-0445-9. [PMID: 25387562]
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