3,4-Methylenedioxyamphetamine (BioDeep_00000018106)

   

human metabolite Chemicals and Drugs


代谢物信息卡片


1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine

化学式: C10H13NO2 (179.09462380000002)
中文名称: 替苯丙胺
谱图信息: 最多检出来源 Health Care Products(drug) 50%

分子结构信息

SMILES: CC(CC1=CC2=C(C=C1)OCO2)N
InChI: InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3

描述信息

An amphetamine derivative that inhibits uptake of catecholamine neurotransmitters. It is a hallucinogen. It is less toxic than its methylated derivative but in sufficient doses may still destroy serotonergic neurons and has been used for that purpose experimentally. [PubChem]; In 1970, the Controlled Substances Act was enacted in the United States, placing MDA into Schedule I. It is similarly controlled in other nations. In Canada MDA is a Schedule III drug. Internationally, MDA is a Schedule I drug under the Convention on Psychotropic Substances. Many similar unscheduled MDxx chemicals can be prosecuted under the Federal Analog Act. MDA (3,4-methylenedioxyamphetamine), also known as tenamfetamine (INN), is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes. It is mainly used as a recreational drug, an entheogen, and a tool in use to supplement various types of practices for transcendence, including in meditation, psychonautics, and as an agent in psychedelic psychotherapy. It was first synthesized by G. Mannish and W. Jacobson in 1910. There are about 20 different synthetic routes described in the literature for its preparation.
D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens
C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant
D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents
D049990 - Membrane Transport Modulators

同义名列表

13 个代谢物同义名

1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine; 1-(1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine; N,alpha-Dimethyl-1,3-benzodioxole-5-ethanamine; 1-(2H-1,3-benzodioxol-5-yl)propan-2-amine; (RS)-3,4-(Methylenedioxy)methamphetamine; N-Methyl-3,4-methylenedioxyamphetamine; 1-(1,3-benzodioxol-5-yl)propan-2-amine; DL-(3,4-Methylenedioxy)methamphetamine; 3,4-methylenedioxymethamphetamine; 3,4-Methylenedioxyamphetamine; 3,4 Methylenedioxyamphetamine; Tenamfetamine; MDMA



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

Reactome(0)

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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)

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。



文献列表

  • Sha Gao, Shuang Gao, Yanuo Wang, Na Li, Zijian Yang, Huiping Yao, Yanwei Chen, Yu Cheng, Yisheng Zhong, Xi Shen. Inhibition of Ferroptosis Ameliorates Photoreceptor Degeneration in Experimental Diabetic Mice. International journal of molecular sciences. 2023 Nov; 24(23):. doi: 10.3390/ijms242316946. [PMID: 38069270]
  • Lu Liu, Xin Guan, Yanqiao Zhao, Xiaona Wang, Chonggao Yin, Qinghua Liu, Hongli Li. [Mechanism of miR-186-5p Regulating PRKAA2 to Promote Ferroptosis 
in Lung Adenocarcinoma Cells]. Zhongguo fei ai za zhi = Chinese journal of lung cancer. 2023 Nov; 26(11):813-821. doi: 10.3779/j.issn.1009-3419.2023.102.39. [PMID: 38061883]
  • Jeffrey Wight, William Doucette. Quantifying the Root-to-Shoot Transfer of 4,4'-Methylenedianiline Using Pressure Chamber and Intact Plant Methods. Environmental toxicology and chemistry. 2023 Mar; 42(3):655-662. doi: 10.1002/etc.5549. [PMID: 36718782]
  • Karolina E Kolaczynska, Paula Ducret, Daniel Trachsel, Marius C Hoener, Matthias E Liechti, Dino Luethi. Pharmacological characterization of 3,4-methylenedioxyamphetamine (MDA) analogs and two amphetamine-based compounds: N,α-DEPEA and DPIA. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology. 2022 06; 59(?):9-22. doi: 10.1016/j.euroneuro.2022.03.006. [PMID: 35378384]
  • Thomas J F Angenoorth, Stevan Stankovic, Marco Niello, Marion Holy, Simon D Brandt, Harald H Sitte, Julian Maier. Interaction Profiles of Central Nervous System Active Drugs at Human Organic Cation Transporters 1-3 and Human Plasma Membrane Monoamine Transporter. International journal of molecular sciences. 2021 Nov; 22(23):. doi: 10.3390/ijms222312995. [PMID: 34884800]
  • Simon D Brandt, Hailey M Walters, John S Partilla, Bruce E Blough, Pierce V Kavanagh, Michael H Baumann. The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats. Psychopharmacology. 2020 Dec; 237(12):3703-3714. doi: 10.1007/s00213-020-05648-z. [PMID: 32875347]
  • Kusumika Saha, Yang Li, Marion Holy, Kurt R Lehner, Mohammad O Bukhari, John S Partilla, Walter Sandtner, Harald H Sitte, Michael H Baumann. The synthetic cathinones, butylone and pentylone, are stimulants that act as dopamine transporter blockers but 5-HT transporter substrates. Psychopharmacology. 2019 Mar; 236(3):953-962. doi: 10.1007/s00213-018-5075-5. [PMID: 30345459]
  • Alex J Krotulski, Amanda L A Mohr, Donna M Papsun, Barry K Logan. Dibutylone (bk-DMBDB): Intoxications, Quantitative Confirmations and Metabolism in Authentic Biological Specimens. Journal of analytical toxicology. 2018 Sep; 42(7):437-445. doi: 10.1093/jat/bky022. [PMID: 29554274]
  • Hideaki Ishii, Andrey B Petrenko, Mika Sasaki, Yukio Satoh, Yoshinori Kamiya, Toshiyuki Tobita, Kenta Furutani, Mari Matsuhashi, Tatsuro Kohno, Hiroshi Baba. Free radical scavenger edaravone produces robust neuroprotection in a rat model of spinal cord injury. Brain research. 2018 03; 1682(?):24-35. doi: 10.1016/j.brainres.2017.12.035. [PMID: 29294349]
  • Chi-Wei Lee, Yu-Ying Chao, Jentaie Shiea, Jheng-Heng Shen, Hei-Hwa Lee, Bai-Hsiun Chen. Ambient mass spectrometry for rapid diagnosis of psychoactive drugs overdose in an unstable patient. The American journal of emergency medicine. 2018 Mar; 36(3):530.e1-530.e5. doi: 10.1016/j.ajem.2017.12.042. [PMID: 29290509]
  • Marie Mardal, Juliet Kinyua, Pedram Ramin, Bram Miserez, Alexander L N Van Nuijs, Adrian Covaci, Markus R Meyer. Screening for illicit drugs in pooled human urine and urinated soil samples and studies on the stability of urinary excretion products of cocaine, MDMA, and MDEA in wastewater by hyphenated mass spectrometry techniques. Drug testing and analysis. 2017 Jan; 9(1):106-114. doi: 10.1002/dta.1957. [PMID: 26888521]
  • Michael A Darracq, Stephen L Thornton, Alicia B Minns, Roy R Gerona. A Case of 3,4-Dimethoxyamphetamine (3,4-DMA) and 3,4-Methylenedioxymethamphetamine (MDMA) Toxicity with Possible Metabolic Interaction. Journal of psychoactive drugs. 2016 Nov; 48(5):351-354. doi: 10.1080/02791072.2016.1225324. [PMID: 27636207]
  • Andrea E Steuer, Martina I Boxler, Lorena Stock, Thomas Kraemer. Inhibition potential of 3,4-methylenedioxymethamphetamine (MDMA) and its metabolites on the in vitro monoamine oxidase (MAO)-catalyzed deamination of the neurotransmitters serotonin and dopamine. Toxicology letters. 2016 Jan; 243(?):48-55. doi: 10.1016/j.toxlet.2015.12.001. [PMID: 26721607]
  • Wei-Yin Hong, Ya-Chun Ko, Mei-Chih Lin, Po-Yu Wang, Yu-Pen Chen, Lih-Ching Chiueh, Daniel Yang-Chih Shih, Hsiu-Kuan Chou, Hwei-Fang Cheng. Determination of Synthetic Cathinones in Urine Using Gas Chromatography-Mass Spectrometry Techniques. Journal of analytical toxicology. 2016 Jan; 40(1):12-6. doi: 10.1093/jat/bkv108. [PMID: 26410364]
  • Andrea E Steuer, Corina Schmidhauser, Yasmin Schmid, Anna Rickli, Matthias E Liechti, Thomas Kraemer. Chiral Plasma Pharmacokinetics of 3,4-Methylenedioxymethamphetamine and its Phase I and II Metabolites following Controlled Administration to Humans. Drug metabolism and disposition: the biological fate of chemicals. 2015 Dec; 43(12):1864-71. doi: 10.1124/dmd.115.066340. [PMID: 26395866]
  • Borbála Molnár, Blanka Fodor, Imre Boldizsár, Ibolya Molnár-Perl. Quantitative Silylation Speciations of Primary Phenylalkyl Amines, Including Amphetamine and 3,4-Methylenedioxyamphetamine Prior to Their Analysis by GC/MS. Analytical chemistry. 2015 Oct; 87(20):10188-92. doi: 10.1021/acs.analchem.5b02599. [PMID: 26412806]
  • Marta Concheiro, Michael H Baumann, Karl B Scheidweiler, Richard B Rothman, Gina F Marrone, Marilyn A Huestis. Nonlinear pharmacokinetics of (+/-)3,4-methylenedioxymethamphetamine (MDMA) and its pharmacodynamic consequences in the rat. Drug metabolism and disposition: the biological fate of chemicals. 2014 Jan; 42(1):119-25. doi: 10.1124/dmd.113.053678. [PMID: 24141857]
  • Camilla Montesano, Manuel Sergi, Mariaelena Moro, Sabino Napoletano, Francesco Saverio Romolo, Michele Del Carlo, Dario Compagnone, Roberta Curini. Screening of methylenedioxyamphetamine- and piperazine-derived designer drugs in urine by LC-MS/MS using neutral loss and precursor ion scan. Journal of mass spectrometry : JMS. 2013 Jan; 48(1):49-59. doi: 10.1002/jms.3115. [PMID: 23303747]
  • Keiko Nakanishi, Munehiro Katagi, Kei Zaitsu, Noriaki Shima, Hiroe Kamata, Akihiro Miki, Hajime Kato, Ken-Ichi Harada, Hitoshi Tsuchihashi, Koichi Suzuki. Simultaneous enantiomeric determination of MDMA and its phase I and phase II metabolites in urine by liquid chromatography-tandem mass spectrometry with chiral derivatization. Analytical and bioanalytical chemistry. 2012 Nov; 404(8):2427-35. doi: 10.1007/s00216-012-6385-9. [PMID: 23010844]
  • Aixin Shi, Xin Hu, Kexin Li, Jian Li, Liping Han, Huayin Wan, Rubing Li. Determination of piperphentonamine and metabolites M1 and M6 in human plasma and urine by LC/MS/MS and its application in a pharmacokinetics study in Chinese healthy volunteers. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Nov; 908(?):87-93. doi: 10.1016/j.jchromb.2012.09.031. [PMID: 23122405]
  • S Lott, F Musshoff, B Madea. Estimation of gamma-hydroxybutyrate (GHB) co-consumption in serum samples of drivers positive for amphetamine or ecstasy. Forensic science international. 2012 Sep; 221(1-3):98-101. doi: 10.1016/j.forsciint.2012.04.009. [PMID: 22554869]
  • Adrienn Dobos, Elod Hidvégi, Gábor Pál Somogyi. Comparison of five derivatizing agents for the determination of amphetamine-type stimulants in human urine by extractive acylation and gas chromatography-mass spectrometry. Journal of analytical toxicology. 2012 Jun; 36(5):340-4. doi: 10.1093/jat/bks026. [PMID: 22582269]
  • Brandon J Warrick, John Wilson, Matthew Hedge, Scott Freeman, Karen Leonard, Cynthia Aaron. Lethal serotonin syndrome after methylone and butylone ingestion. Journal of medical toxicology : official journal of the American College of Medical Toxicology. 2012 Mar; 8(1):65-8. doi: 10.1007/s13181-011-0199-6. [PMID: 22160789]
  • Hyeyoung Choi, Seungkyung Baeck, Moonhee Jang, Sooyeun Lee, Hwakyung Choi, Heesun Chung. Simultaneous analysis of psychotropic phenylalkylamines in oral fluid by GC-MS with automated SPE and its application to legal cases. Forensic science international. 2012 Feb; 215(1-3):81-7. doi: 10.1016/j.forsciint.2011.02.011. [PMID: 21377815]
  • Cédric M Hysek, Robin Brugger, Linda D Simmler, Marcel Bruggisser, Massimiliano Donzelli, Eric Grouzmann, Marius C Hoener, Matthias E Liechti. Effects of the α₂-adrenergic agonist clonidine on the pharmacodynamics and pharmacokinetics of 3,4-methylenedioxymethamphetamine in healthy volunteers. The Journal of pharmacology and experimental therapeutics. 2012 Feb; 340(2):286-94. doi: 10.1124/jpet.111.188425. [PMID: 22034656]
  • Samanta Yubero-Lahoz, Mario A Ayestas, Bruce E Blough, John S Partilla, Richard B Rothman, Rafael de la Torre, Michael H Baumann. Effects of MDMA and related analogs on plasma 5-HT: relevance to 5-HT transporters in blood and brain. European journal of pharmacology. 2012 Jan; 674(2-3):337-44. doi: 10.1016/j.ejphar.2011.10.033. [PMID: 22079770]
  • Cédric M Hysek, Linda D Simmler, Valentina G Nicola, Nerina Vischer, Massimiliano Donzelli, Stephan Krähenbühl, Eric Grouzmann, Jörg Huwyler, Marius C Hoener, Matthias E Liechti. Duloxetine inhibits effects of MDMA ('ecstasy') in vitro and in humans in a randomized placebo-controlled laboratory study. PloS one. 2012; 7(5):e36476. doi: 10.1371/journal.pone.0036476. [PMID: 22574166]
  • Kenji Kuwayama, Kenji Tsujikawa, Hajime Miyaguchi, Tatsuyuki Kanamori, Yuko T Iwata, Hiroyuki Inoue. Rapid, simple, and highly sensitive analysis of drugs in biological samples using thin-layer chromatography coupled with matrix-assisted laser desorption/ionization mass spectrometry. Analytical and bioanalytical chemistry. 2012 Jan; 402(3):1257-67. doi: 10.1007/s00216-011-5576-0. [PMID: 22147272]
  • Yoshiyuki Goto, Shiho Takeda, Toshinori Araki, Takayuki Fuchigami. Method of simultaneous stir bar sorptive extraction of phenethylamines and THC metabolite from urine. The Journal of toxicological sciences. 2011 Oct; 36(5):523-9. doi: 10.2131/jts.36.523. [PMID: 22008528]
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  • Melanie Mueller, Amy K Goodwin, Nancy A Ator, Una D McCann, George A Ricaurte. Metabolism and disposition of 3,4-methylenedioxymethamphetamine ('ecstasy') in baboons after oral administration: comparison with humans reveals marked differences. The Journal of pharmacology and experimental therapeutics. 2011 Jul; 338(1):310-7. doi: 10.1124/jpet.111.180612. [PMID: 21493752]
  • Kenji Tsujikawa, Toshiyasu Mikuma, Kenji Kuwayama, Hajime Miyaguchi, Tatsuyuki Kanamori, Yuko T Iwata, Hiroyuki Inoue. Urinary excretion profiles of N-hydroxy-3,4-methylenedioxymethamphetamine in rats. Xenobiotica; the fate of foreign compounds in biological systems. 2011 Jul; 41(7):578-84. doi: 10.3109/00498254.2011.565821. [PMID: 21425955]
  • Birthe Schubert, Herbert Oberacher. Impact of solvent conditions on separation and detection of basic drugs by micro liquid chromatography-mass spectrometry under overloading conditions. Journal of chromatography. A. 2011 Jun; 1218(22):3413-22. doi: 10.1016/j.chroma.2011.03.051. [PMID: 21530972]
  • Hei Hwa Lee, Jong Feng Lee, Sin Yu Lin, Ping Ho Chen, Bai Hsiun Chen. Simultaneous determination of HFBA-derivatized amphetamines and ketamines in urine by gas chromatography-mass spectrometry. Journal of analytical toxicology. 2011 Apr; 35(3):162-9. doi: 10.1093/anatox/35.3.162. [PMID: 21439152]
  • Dominik K Biezonski, Jerrold S Meyer. The Nature of 3, 4-Methylenedioxymethamphetamine (MDMA)-Induced Serotonergic Dysfunction: Evidence for and Against the Neurodegeneration Hypothesis. Current neuropharmacology. 2011 Mar; 9(1):84-90. doi: 10.2174/157015911795017146. [PMID: 21886568]
  • Yvonne M McNamara, Suzanne M Cloonan, Andrew J S Knox, John J Keating, Stephen G Butler, Günther H Peters, Mary J Meegan, D Clive Williams. Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents. Bioorganic & medicinal chemistry. 2011 Feb; 19(3):1328-48. doi: 10.1016/j.bmc.2010.11.054. [PMID: 21227702]
  • Jingbin Zeng, Jing Zou, Xinhong Song, Jinmei Chen, Jiaojiao Ji, Bo Wang, Yiru Wang, Jaeho Ha, Xi Chen. A new strategy for basic drug extraction in aqueous medium using electrochemically enhanced solid-phase microextraction. Journal of chromatography. A. 2011 Jan; 1218(2):191-6. doi: 10.1016/j.chroma.2010.11.020. [PMID: 21159350]
  • Maiko Kawamura, Ruri Kikura-Hanajiri, Yukihiro Goda. [Simple and rapid screening for methamphetamine and 3,4-methylenedioxymethamphetamine (MDMA) and their metabolites in urine using direct analysis in real time (DART)-TOFMS]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2011; 131(5):827-33. doi: 10.1248/yakushi.131.827. [PMID: 21532279]
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