3,4-Methylenedioxymethamphetamine (BioDeep_00000180683)
Secondary id: BioDeep_00000002021, BioDeep_00001867771
human metabolite blood metabolite
代谢物信息卡片
Hydrochloride, N-methyl-3,4-methylenedioxyamphetamine
化学式: C11H15NO2 (193.110273)
中文名称: (+/-)-3,4-亚甲基二氧基甲基苯丙胺
谱图信息:
最多检出来源 Homo sapiens(blood) 5.13%
分子结构信息
SMILES: CC(CC1=CC2=C(C=C1)OCO2)NC
InChI: InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3
描述信息
D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant
D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents
D049990 - Membrane Transport Modulators
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
同义名列表
17 个代谢物同义名
Hydrochloride, N-methyl-3,4-methylenedioxyamphetamine; [1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine; N Methyl 3,4 methylenedioxyamphetamine hydrochloride; N-Methyl-3,4-methylenedioxyamphetamine hydrochloride; 1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine; N,alpha-Dimethyl-1,3-benzodioxole-5-ethanamine; N,a-Dimethyl-1,3-benzodioxole-5-ethanamine; N,Α-dimethyl-1,3-benzodioxole-5-ethanamine; (RS)-3,4-(Methylenedioxy)methamphetamine; N-Methyl-3,4-methylenedioxyamphetamine; DL-(3,4-Methylenedioxy)methamphetamine; N Methyl 3,4 methylenedioxyamphetamine; 3,4-methylenedioxymethamphetamine; Methylenedioxymethamphetamine; Ecstasy (drug); Ecstasy; MDMA
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:1391
- KEGG: C07577
- PubChem: 1615
- HMDB: HMDB0254382
- DrugBank: DB01454
- ChEMBL: CHEMBL43048
- Wikipedia: MDMA
- MeSH: N-Methyl-3,4-methylenedioxyamphetamine
- chemspider: 1556
- CAS: 42542-10-9
- CAS: 54946-52-0
- PubChem: 9780
- NIKKAJI: J276.360E
- RefMet: 3,4-Methylenedioxymethamphetamine
- RefMet: Methylenedioxymethamphetamine
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
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
- Marina Bellot, Fernando Soria, Raul López-Arnau, Cristian Gómez-Canela, Carlos Barata. Daphnia magna an emerging environmental model of neuro and cardiotoxicity of illicit drugs.
Environmental pollution (Barking, Essex : 1987).
2024 Jan; 344(?):123355. doi:
10.1016/j.envpol.2024.123355. [PMID: 38228265] - Nikolaos Rousis, Richard Bade, Iván Romero-Sánchez, Jochen F Mueller, Nikolaos S Thomaidis, Kevin V Thomas, Emma Gracia-Lor. Festivals following the easing of COVID-19 restrictions: Prevalence of new psychoactive substances and illicit drugs.
Environment international.
2023 Jun; 178(?):108075. doi:
10.1016/j.envint.2023.108075. [PMID: 37399770] - Beatrice De Felice, Marco Parolini. Exposure to 3,4-methylenedioxymethamphetamine (MDMA) induced biochemical but not behavioral effects in Daphnia magna.
Environmental toxicology and pharmacology.
2023 May; 100(?):104163. doi:
10.1016/j.etap.2023.104163. [PMID: 37257268] - Abdelmounaim Baslam, Abdelfatah Aitbaba, Asmae Lamrani Hanchi, Zakaria Tazart, Rachida Aboufatima, Nabila Soraa, Mohamed Ait-El-Mokhtar, Samia Boussaa, Marouane Baslam, Abderrahman Chait. Modulation of Gut Microbiome in Ecstasy/MDMA-Induced Behavioral and Biochemical Impairment in Rats and Potential of Post-Treatment with Anacyclus pyrethrum L. Aqueous Extract to Mitigate Adverse Effects.
International journal of molecular sciences.
2023 May; 24(10):. doi:
10.3390/ijms24109086. [PMID: 37240429] - 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] - Yu-Hsiung Chen, Mu-Hong Chen, Han-Ting Wei, Lian-Yu Chen. Survey of substance use among adolescent drug offenders referred from juvenile courts in Taiwan: Clinical epidemiology of single versus multiple illicit substance use.
Journal of the Formosan Medical Association = Taiwan yi zhi.
2022 Nov; 121(11):2257-2264. doi:
10.1016/j.jfma.2022.04.009. [PMID: 35484001] - Roberta Zilles Hahn, Marcos Frank Bastiani, Lilian de Lima Feltraco Lizot, Anelise Schneider, Isabela Caroline da Silva Moreira, Yasmin Fazenda Meireles, Mariana Freitas Viana, Carlos Augusto do Nascimento, Rafael Linden. Long-term monitoring of drug consumption patterns during the COVID-19 pandemic in a small-sized community in Brazil through wastewater-based epidemiology.
Chemosphere.
2022 Sep; 302(?):134907. doi:
10.1016/j.chemosphere.2022.134907. [PMID: 35561781] - Andrea Estévez-Danta, Lubertus Bijlsma, Ricardo Capela, Rafael Cela, Alberto Celma, Félix Hernández, Unax Lertxundi, João Matias, Rosa Montes, Gorka Orive, Ailette Prieto, Miguel M Santos, Rosario Rodil, José Benito Quintana. Use of illicit drugs, alcohol and tobacco in Spain and Portugal during the COVID-19 crisis in 2020 as measured by wastewater-based epidemiology.
The Science of the total environment.
2022 Aug; 836(?):155697. doi:
10.1016/j.scitotenv.2022.155697. [PMID: 35523346] - Chen Li, Dongfang Han, Zhifang Wu, Zhishan Liang, Fangjie Han, Ke Chen, Wencai Fu, Dongxue Han, Yukai Wang, Li Niu. Polydopamine-based molecularly imprinted electrochemical sensor for the highly selective determination of ecstasy components.
The Analyst.
2022 Jul; 147(14):3291-3297. doi:
10.1039/d2an00351a. [PMID: 35726908] - Chi-Jung Tsai, Chuang-Hsin Chiu, Yu-Yeh Kuo, Wen-Sheng Huang, Tsung-Hsun Yu, Leo Garcia Flores, Skye Hsin-Hsien Yeh, Kuo-Hsing Ma. Amitriptyline Accelerates SERT Binding Recovery in a Rat 3,4-Methylenedioxymethamphetamine (MDMA) Model: In Vivo 4-[18F]-ADAM PET Imaging.
International journal of molecular sciences.
2022 Jun; 23(13):. doi:
10.3390/ijms23137035. [PMID: 35806049] - 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] - Tim Boogaerts, Maarten Quireyns, Maarten De Prins, Bram Pussig, Hans De Loof, Catharina Matheï, Bert Aertgeerts, Virginie Van Coppenolle, Erik Fransen, Adrian Covaci, Alexander L N van Nuijs. Temporal monitoring of stimulants during the COVID-19 pandemic in Belgium through the analysis of influent wastewater.
The International journal on drug policy.
2022 06; 104(?):103679. doi:
10.1016/j.drugpo.2022.103679. [PMID: 35427945] - Ángel A Islas, Thomas Scior. Allosteric Binding of MDMA to the Human Serotonin Transporter (hSERT) via Ensemble Binding Space Analysis with ΔG Calculations, Induced Fit Docking and Monte Carlo Simulations.
Molecules (Basel, Switzerland).
2022 May; 27(9):. doi:
10.3390/molecules27092977. [PMID: 35566327] - Eleftherios Mellos, Thomas Paparrigopoulos. Substance use during the COVID-19 pandemic: What is really happening?.
Psychiatrike = Psychiatriki.
2022 Mar; 33(1):17-20. doi:
10.22365/jpsych.2022.072. [PMID: 35255473] - Naomi Reymond, Erik Emke, Thea Boucheron, Thomas Ter Laak, Pim de Voogt, Pierre Esseiva, Frederic Been. Retrospective suspect and non-target screening combined with similarity measures to prioritize MDMA and amphetamine synthesis markers in wastewater.
The Science of the total environment.
2022 Mar; 811(?):152139. doi:
10.1016/j.scitotenv.2021.152139. [PMID: 34871677] - Derek C Waggoner, Sarah R Delaney, Nichole L Korpi-Steiner. Comparative Analyses of Three Point-of-Care Urine Drug Test Devices' Performance Characteristics for Use in Ambulatory Clinic Settings.
The journal of applied laboratory medicine.
2022 03; 7(2):495-502. doi:
10.1093/jalm/jfab095. [PMID: 34597363] - André Niebel, Fritz Pragst, Franziska Krumbiegel, Sven Hartwig. Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs.
Forensic science international.
2022 Feb; 331(?):111148. doi:
10.1016/j.forsciint.2021.111148. [PMID: 34923263] - Matthew J A O'Reilly, Christine A Harvey, Robin Auld, Michelle Cretikos, Catherine Francis, Stephanie Todd, Daniel Barry, Una Cullinan, Michael Symonds. A quantitative analysis of MDMA seized at New South Wales music festivals over the 2019/2020 season: Form, purity, dose and adulterants.
Drug and alcohol review.
2022 02; 41(2):330-337. doi:
10.1111/dar.13412. [PMID: 34919770] - Olivia Price, Nicola Man, Raimondo Bruno, Paul Dietze, Caroline Salom, Simon Lenton, Jodie Grigg, Daisy Gibbs, Tanya Wilson, Louisa Degenhardt, Roanna Chan, Natalie Thomas, Amy Peacock. Changes in illicit drug use and markets with the COVID-19 pandemic and associated restrictions: findings from the Ecstasy and Related Drugs Reporting System, 2016-20.
Addiction (Abingdon, England).
2022 01; 117(1):182-194. doi:
10.1111/add.15620. [PMID: 34159666] - Foke L van de Blaak, Glenn J H Dumont. Serotonin transporter availability, neurocognitive function and their correlation in abstinent 3,4-methylenedioxymethamphetamine users.
Human psychopharmacology.
2022 01; 37(1):e2811. doi:
10.1002/hup.2811. [PMID: 34506649] - Seyyed Majid Eslami, Laleh Khorshidi, Maryam Ghasemi, Amir Rashidian, Mahdi Mirghazanfari, Akram Nezhadi, Mohsen Chamanara, Ruhollah Mirjani. Protective effects of atorvastatin and rosuvastatin on 3,4-methylenedioxymethamphetamine (MDMA)-induced spatial learning and memory impairment.
Inflammopharmacology.
2021 Dec; 29(6):1807-1818. doi:
10.1007/s10787-021-00891-y. [PMID: 34780009] - Viktor Román, Rita Kedves, Kristóf Kelemen, Zsolt Némethy, Beáta Sperlágh, Balázs Lendvai, E Sylvester Vizi. Contribution of analog signaling to neurotransmitter interactions and behavior: Role of transporter-mediated nonquantal dopamine release.
Physiological reports.
2021 11; 9(21):e15088. doi:
10.14814/phy2.15088. [PMID: 34762352] - Golshad Kowsari, Soraya Mehrabi, Sara Soleimani Asl, Mahsa Pourhamzeh, Kazem Mousavizadeh, Mehdi Mehdizadeh. Nicotine and modafinil combination protects against the neurotoxicity induced by 3,4-Methylenedioxymethamphetamine in hippocampal neurons of male rats.
Journal of chemical neuroanatomy.
2021 10; 116(?):101986. doi:
10.1016/j.jchemneu.2021.101986. [PMID: 34119664] - Joseph J Palamar, Patricia Acosta. Virtual raves and happy hours during COVID-19: New drug use contexts for electronic dance music partygoers.
The International journal on drug policy.
2021 07; 93(?):102904. doi:
10.1016/j.drugpo.2020.102904. [PMID: 32861536] - Anna Borissova, Bart Ferguson, Matthew B Wall, Celia Ja Morgan, Robin L Carhart-Harris, Mark Bolstridge, Michael Ap Bloomfield, Tim M Williams, Amanda Feilding, Kevin Murphy, Robin J Tyacke, David Erritzoe, Lorna Stewart, Kim Wolff, David Nutt, H Valerie Curran, Will Lawn. Acute effects of MDMA on trust, cooperative behaviour and empathy: A double-blind, placebo-controlled experiment.
Journal of psychopharmacology (Oxford, England).
2021 05; 35(5):547-555. doi:
10.1177/0269881120926673. [PMID: 32538252] - Erich Studerus, Patrick Vizeli, Samuel Harder, Laura Ley, Matthias E Liechti. Prediction of MDMA response in healthy humans: a pooled analysis of placebo-controlled studies.
Journal of psychopharmacology (Oxford, England).
2021 05; 35(5):556-565. doi:
10.1177/0269881121998322. [PMID: 33781103] - Francesca Bedussi, Elisabetta Acerbis, Roberta Noseda, Davide Demagistri, Emanuela Zamprogno, Alessandro Ceschi. False-positive urine screen test for MDMA in a patient exposed to mebeverine.
British journal of clinical pharmacology.
2021 05; 87(5):2397-2398. doi:
10.1111/bcp.14624. [PMID: 33200465] - C Abuin-Martínez, R Vidal, M D Gutiérrez-López, M Pérez-Hernández, P Giménez-Gómez, N Morales-Puerto, E O'Shea, M I Colado. Increased kynurenine concentration attenuates serotonergic neurotoxicity induced by 3,4-methylenedioxymethamphetamine (MDMA) in rats through activation of aryl hydrocarbon receptor.
Neuropharmacology.
2021 04; 187(?):108490. doi:
10.1016/j.neuropharm.2021.108490. [PMID: 33607146] - Fernando B de Moura, Alexander Sherwood, Thomas E Prisinzano, Carol A Paronis, Jack Bergman, Stephen J Kohut. Reinforcing effects of synthetic cathinones in rhesus monkeys: Dose-response and behavioral economic analyses.
Pharmacology, biochemistry, and behavior.
2021 03; 202(?):173112. doi:
10.1016/j.pbb.2021.173112. [PMID: 33444603] - Alex J Krotulski, Donna M Papsun, Chris W Chronister, Joseph Homan, Michele M Crosby, Jennifer Hoyer, Bruce A Goldberger, Barry K Logan. Eutylone Intoxications-An Emerging Synthetic Stimulant in Forensic Investigations.
Journal of analytical toxicology.
2021 Feb; 45(1):8-20. doi:
10.1093/jat/bkaa113. [PMID: 33325503] - Melike Aydoğdu, Serap Annette Akgür. Urine drug-testing tampering approaches: Turkish probationers.
Medicine, science, and the law.
2021 Jan; 61(1):6-13. doi:
10.1177/0025802420956453. [PMID: 32924786] - Allison N White, Joshua D Gross, Shane W Kaski, Kristen R Trexler, Kim A Wix, William C Wetsel, Steven G Kinsey, David P Siderovski, Vincent Setola. Genetic deletion of Rgs12 in mice affects serotonin transporter expression and function in vivo and ex vivo.
Journal of psychopharmacology (Oxford, England).
2020 12; 34(12):1393-1407. doi:
10.1177/0269881120944160. [PMID: 32842837] - Arash Ghaffari-Rafi, Ki Suk Eum, Jesus Villanueva, Jay Jahanmir. Protracted hyperthermia and delayed rhabdomyolysis in ecstasy toxicity: A case report.
Medicine.
2020 Oct; 99(41):e21842. doi:
10.1097/md.0000000000021842. [PMID: 33031256] - Celalettin Dagli, Ipek Duman. Successful Use of Early Therapeutic Hypothermia in an MDMA and Amphetamine Intoxication-Induced Out-of-Hospital Cardiac Arrest: A Case Report.
The Journal of emergency medicine.
2020 Sep; 59(3):e89-e92. doi:
10.1016/j.jemermed.2020.06.019. [PMID: 32712033] - João Francisco Allochio Filho, Nayara A Dos Santos, Keyller Bastos Borges, Valdemar Lacerda, Fabrício Souza Pelição, Wanderson Romão. Fiber spray ionization mass spectrometry in forensic chemistry: A screening of drugs of abuse and direct determination of cocaine in urine.
Rapid communications in mass spectrometry : RCM.
2020 Sep; 34 Suppl 3(?):e8747. doi:
10.1002/rcm.8747. [PMID: 32056289] - Ana Carolina Faria, Helena Carmo, Félix Carvalho, João Pedro Silva, Maria de Lourdes Bastos, Diana Dias da Silva. Drinking to death: Hyponatraemia induced by synthetic phenethylamines.
Drug and alcohol dependence.
2020 07; 212(?):108045. doi:
10.1016/j.drugalcdep.2020.108045. [PMID: 32460203] - Gabriel Baltazar-Martins, Maria Del Mar Plata, Jesús Muñoz-Guerra, Javier Argaya, Juan Del Coso. Chronicle of an unintentional MDMA intoxication of a field hockey team to prevent its qualification for the Beijing 2008 Olympics: A case report.
Drug testing and analysis.
2020 May; 12(5):647-650. doi:
10.1002/dta.2753. [PMID: 31881120] - Yu Chen, Huyen T N Tran, Yasir H Saber, F Scott Hall. High ambient temperature increases the toxicity and lethality of 3,4-methylenedioxymethamphetamine and methcathinone.
Pharmacology, biochemistry, and behavior.
2020 05; 192(?):172912. doi:
10.1016/j.pbb.2020.172912. [PMID: 32201298] - Marion Leclercq, Marion Soichot, Brigitte Delhotal-Landes, Emmanuel Bourgogne, Hervé Gourlain, Bruno Mégarbane, Laurence Labat. False positive amphetamines and 3,4-methylenedioxymethamphetamine immunoassays in the presence of metoprolol-two cases reported in clinical toxicology.
Journal of analytical toxicology.
2020 Mar; 44(2):200-205. doi:
10.1093/jat/bkz051. [PMID: 31384953] - G Taghizadeh, H Mehdizadeh, H Lavasani, Y Hosseinzadeh Ardakani, A Foroumadi, Z Halvaei Khankahdani, A Moshtagh, J Pourahmad, M Sharifzadeh, M R Rouini. Dose concentration and spatial memory and brain mitochondrial function association after 3,4-methylenedioxymethamphetamine (MDMA) administration in rats.
Archives of toxicology.
2020 03; 94(3):911-925. doi:
10.1007/s00204-020-02673-x. [PMID: 32067070] - Mathilde Millot, Yosuke Saga, Sandra Duperrier, Elise Météreau, Maude Beaudoin-Gobert, Véronique Sgambato. Prior MDMA administration aggravates MPTP-induced Parkinsonism in macaque monkeys.
Neurobiology of disease.
2020 02; 134(?):104643. doi:
10.1016/j.nbd.2019.104643. [PMID: 31689516] - Friederike Holze, Patrick Vizeli, Felix Müller, Laura Ley, Raoul Duerig, Nimmy Varghese, Anne Eckert, Stefan Borgwardt, Matthias E Liechti. Distinct acute effects of LSD, MDMA, and D-amphetamine in healthy subjects.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2020 02; 45(3):462-471. doi:
10.1038/s41386-019-0569-3. [PMID: 31733631] - Iria González-Mariño, Jose Antonio Baz-Lomba, Nikiforos A Alygizakis, Maria Jesús Andrés-Costa, Richard Bade, Anne Bannwarth, Leon P Barron, Frederic Been, Lisa Benaglia, Jean-Daniel Berset, Lubertus Bijlsma, Igor Bodík, Asher Brenner, Andreas L Brock, Daniel A Burgard, Erika Castrignanò, Alberto Celma, Christophoros E Christophoridis, Adrian Covaci, Olivier Delémont, Pim de Voogt, Damien A Devault, Mário J Dias, Erik Emke, Pierre Esseiva, Despo Fatta-Kassinos, Ganna Fedorova, Konstantinos Fytianos, Cobus Gerber, Roman Grabic, Emma Gracia-Lor, Stefan Grüner, Teemu Gunnar, Evroula Hapeshi, Ester Heath, Björn Helm, Félix Hernández, Aino Kankaanpaa, Sara Karolak, Barbara Kasprzyk-Hordern, Ivona Krizman-Matasic, Foon Yin Lai, Wojciech Lechowicz, Alvaro Lopes, Miren López de Alda, Ester López-García, Arndís S C Löve, Nicola Mastroianni, Gillian L McEneff, Rosa Montes, Kelly Munro, Thomas Nefau, Herbert Oberacher, Jake W O'Brien, Reinhard Oertel, Kristin Olafsdottir, Yolanda Picó, Benedek G Plósz, Fabio Polesel, Cristina Postigo, José Benito Quintana, Pedram Ramin, Malcolm J Reid, Jack Rice, Rosario Rodil, Noelia Salgueiro-González, Sara Schubert, Ivan Senta, Susana M Simões, Maja M Sremacki, Katarzyna Styszko, Senka Terzic, Nikolaos S Thomaidis, Kevin V Thomas, Ben J Tscharke, Robin Udrisard, Alexander L N van Nuijs, Viviane Yargeau, Ettore Zuccato, Sara Castiglioni, Christoph Ort. Spatio-temporal assessment of illicit drug use at large scale: evidence from 7 years of international wastewater monitoring.
Addiction (Abingdon, England).
2020 01; 115(1):109-120. doi:
10.1111/add.14767. [PMID: 31642141] - Boris D Heifets, Juliana S Salgado, Madison D Taylor, Paul Hoerbelt, Daniel F Cardozo Pinto, Elizabeth E Steinberg, Jessica J Walsh, Ji Y Sze, Robert C Malenka. Distinct neural mechanisms for the prosocial and rewarding properties of MDMA.
Science translational medicine.
2019 12; 11(522):. doi:
10.1126/scitranslmed.aaw6435. [PMID: 31826983] - Ricardo Alves Bernardo, Lidya Cardozo da Silva, Maria Eugênia C Queiroz, Boniek Gontijo Vaz, Andréa Rodrigues Chaves. Lab-made solid phase microextraction phases for off line extraction and direct mass spectrometry analysis: Evaluating the extraction parameters.
Journal of chromatography. A.
2019 Oct; 1603(?):23-32. doi:
10.1016/j.chroma.2019.06.038. [PMID: 31230878] - David Erritzoe, James Smith, Patrick M Fisher, Robin Carhart-Harris, Vibe G Frokjaer, Gitte M Knudsen. Recreational use of psychedelics is associated with elevated personality trait openness: Exploration of associations with brain serotonin markers.
Journal of psychopharmacology (Oxford, England).
2019 09; 33(9):1068-1075. doi:
10.1177/0269881119827891. [PMID: 30816797] - Patrick Vizeli, Henriette E Meyer Zu Schwabedissen, Matthias E Liechti. Role of Serotonin Transporter and Receptor Gene Variations in the Acute Effects of MDMA in Healthy Subjects.
ACS chemical neuroscience.
2019 07; 10(7):3120-3131. doi:
10.1021/acschemneuro.8b00590. [PMID: 30589533] - Dino Luethi, Karolina E Kolaczynska, Melanie Walter, Masaki Suzuki, Kenner C Rice, Bruce E Blough, Marius C Hoener, Michael H Baumann, Matthias E Liechti. Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems.
Journal of psychopharmacology (Oxford, England).
2019 07; 33(7):831-841. doi:
10.1177/0269881119844185. [PMID: 31038382] - Anne Zwartsen, Carlijn H C Litjens, Laura Hondebrink, Jeroen J M W van den Heuvel, Rick Greupink, Frans G M Russel, Dylan W de Lange, Juliette Legler, Jan B Koenderink, Remco H S Westerink. Differential effects of psychoactive substances on human wildtype and polymorphic T356M dopamine transporters (DAT).
Toxicology.
2019 06; 422(?):69-75. doi:
10.1016/j.tox.2019.04.012. [PMID: 31009648] - Anna Rickli, Karolina Kolaczynska, Marius C Hoener, Matthias E Liechti. Pharmacological characterization of the aminorex analogs 4-MAR, 4,4'-DMAR, and 3,4-DMAR.
Neurotoxicology.
2019 05; 72(?):95-100. doi:
10.1016/j.neuro.2019.02.011. [PMID: 30776375] - Jui-Hu Shih, Chuang-Hsin Chiu, Kuo-Hsing Ma, Yuahn-Sieh Huang, Chyng-Yann Shiue, Ting-Yin Yeh, Li-Ting Kao, Yang-Yi Lin, I-Hsun Li. Autophagy inhibition plays a protective role against 3, 4-methylenedioxymethamphetamine (MDMA)-induced loss of serotonin transporters and depressive-like behaviors in rats.
Pharmacological research.
2019 04; 142(?):283-293. doi:
10.1016/j.phrs.2019.02.026. [PMID: 30826457] - Stefania Schiavone, Margherita Neri, Angela Bruna Maffione, Paolo Frisoni, Maria Grazia Morgese, Luigia Trabace, Emanuela Turillazzi. Increased iNOS and Nitrosative Stress in Dopaminergic Neurons of MDMA-Exposed Rats.
International journal of molecular sciences.
2019 Mar; 20(5):. doi:
10.3390/ijms20051242. [PMID: 30871034] - Eulàlia Olesti, Ilario De Toma, Johannes G Ramaekers, Tibor M Brunt, Marcel Lí Carbó, Cristina Fernández-Avilés, Patricia Robledo, Magí Farré, Mara Dierssen, Óscar J Pozo, Rafael de la Torre. Metabolomics predicts the pharmacological profile of new psychoactive substances.
Journal of psychopharmacology (Oxford, England).
2019 03; 33(3):347-354. doi:
10.1177/0269881118812103. [PMID: 30451567] - Michaela Pettie, Alana Oakly, David N Harper, Bart A Ellenbroek. A genetic deletion of the serotonin transporter differentially influences the behavioural effects of MDMA.
Journal of psychopharmacology (Oxford, England).
2019 03; 33(3):355-363. doi:
10.1177/0269881118822156. [PMID: 30665313] - Lilian H J Richter, Andreas Beck, Veit Flockerzi, Hans H Maurer, Markus R Meyer. Cytotoxicity of new psychoactive substances and other drugs of abuse studied in human HepG2 cells using an adopted high content screening assay.
Toxicology letters.
2019 Feb; 301(?):79-89. doi:
10.1016/j.toxlet.2018.11.007. [PMID: 30465810] - Maude Beaudoin-Gobert, Elise Météreau, Sandra Duperrier, Stéphane Thobois, Léon Tremblay, Véronique Sgambato. Pathophysiology of levodopa-induced dyskinesia: Insights from multimodal imaging and immunohistochemistry in non-human primates.
NeuroImage.
2018 12; 183(?):132-141. doi:
10.1016/j.neuroimage.2018.08.016. [PMID: 30102999] - Mami Nakamura, Kaori Shintani-Ishida, Hiroshi Ikegaya. 5-HT2A Receptor Agonist-Induced Hyperthermia Is Induced via Vasoconstriction by Peripheral 5-HT2A Receptors and Brown Adipose Tissue Thermogenesis by Peripheral Serotonin Loss at a High Ambient Temperature.
The Journal of pharmacology and experimental therapeutics.
2018 11; 367(2):356-362. doi:
10.1124/jpet.118.250217. [PMID: 30206108] - Ana Margarida Araújo, Maria de Lourdes Bastos, Eduarda Fernandes, Félix Carvalho, Márcia Carvalho, Paula Guedes de Pinho. GC-MS metabolomics reveals disturbed metabolic pathways in primary mouse hepatocytes exposed to subtoxic levels of 3,4-methylenedioxymethamphetamine (MDMA).
Archives of toxicology.
2018 11; 92(11):3307-3323. doi:
10.1007/s00204-018-2314-9. [PMID: 30255327] - Gabriella Zsilla, Daniella E Hegyi, Mária Baranyi, E Sylvester Vizi. 3,4-Methylenedioxymethamphetamine, mephedrone, and β-phenylethylamine release dopamine from the cytoplasm by means of transporters and keep the concentration high and constant by blocking reuptake.
European journal of pharmacology.
2018 Oct; 837(?):72-80. doi:
10.1016/j.ejphar.2018.08.037. [PMID: 30172789] - Eric Edsinger, Gül Dölen. A Conserved Role for Serotonergic Neurotransmission in Mediating Social Behavior in Octopus.
Current biology : CB.
2018 10; 28(19):3136-3142.e4. doi:
10.1016/j.cub.2018.07.061. [PMID: 30245101] - 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] - Katelyn S Foppe, Dena R Hammond-Weinberger, Bikram Subedi. Estimation of the consumption of illicit drugs during special events in two communities in Western Kentucky, USA using sewage epidemiology.
The Science of the total environment.
2018 Aug; 633(?):249-256. doi:
10.1016/j.scitotenv.2018.03.175. [PMID: 29574368] - Martina I Boxler, Gabriel L Streun, Matthias E Liechti, Yasmin Schmid, Thomas Kraemer, Andrea E Steuer. Human Metabolome Changes after a Single Dose of 3,4-Methylenedioxymethamphetamine (MDMA) with Special Focus on Steroid Metabolism and Inflammation Processes.
Journal of proteome research.
2018 08; 17(8):2900-2907. doi:
10.1021/acs.jproteome.8b00438. [PMID: 29947220] - Julian Maier, Felix P Mayer, Dino Luethi, Marion Holy, Kathrin Jäntsch, Harald Reither, Lena Hirtler, Marius C Hoener, Matthias E Liechti, Christian Pifl, Simon D Brandt, Harald H Sitte. The psychostimulant (±)-cis-4,4'-dimethylaminorex (4,4'-DMAR) interacts with human plasmalemmal and vesicular monoamine transporters.
Neuropharmacology.
2018 08; 138(?):282-291. doi:
10.1016/j.neuropharm.2018.06.018. [PMID: 29908239] - R Feio-Azevedo, V M Costa, D J Barbosa, A Teixeira-Gomes, I Pita, S Gomes, F C Pereira, M Duarte-Araújo, J A Duarte, F Marques, E Fernandes, M L Bastos, F Carvalho, J P Capela. Aged rats are more vulnerable than adolescents to 'ecstasy'-induced toxicity.
Archives of toxicology.
2018 07; 92(7):2275-2295. doi:
10.1007/s00204-018-2226-8. [PMID: 29869127] - Balázs Szigeti, Adam R Winstock, David Erritzoe, Larissa J Maier. Are ecstasy induced serotonergic alterations overestimated for the majority of users?.
Journal of psychopharmacology (Oxford, England).
2018 07; 32(7):741-748. doi:
10.1177/0269881118767646. [PMID: 29733742] - John D Gilbert, Roger W Byard. Fatal Diabetic Ketoacidosis-A Potential Complication of MDMA (Ecstasy) Use.
Journal of forensic sciences.
2018 May; 63(3):939-941. doi:
10.1111/1556-4029.13602. [PMID: 28766722] - Sean B Dolan, Zhenglan Chen, Renqi Huang, Michael B Gatch. "Ecstasy" to addiction: Mechanisms and reinforcing effects of three synthetic cathinone analogs of MDMA.
Neuropharmacology.
2018 05; 133(?):171-180. doi:
10.1016/j.neuropharm.2018.01.020. [PMID: 29378213] - Francesca Romana Rizzo, Mauro Federici, Nicola Biagio Mercuri. 3,4-Methylenedioxymethamphetamine (MDMA) Alters Synaptic Dopamine Release in the Dorsal Striatum Through Nicotinic Receptors and DAT Inhibition.
Neuroscience.
2018 05; 377(?):69-76. doi:
10.1016/j.neuroscience.2018.02.037. [PMID: 29510210] - Lotte Christine Groth Hoegberg, Cecilie Christiansen, Jesper Soe, Rasmus Telving, Mette Findal Andreasen, Dan Staerk, Lona Louring Christrup, Kenneth Thermann Kongstad. Recreational drug use at a major music festival: trend analysis of anonymised pooled urine.
Clinical toxicology (Philadelphia, Pa.).
2018 04; 56(4):245-255. doi:
10.1080/15563650.2017.1360496. [PMID: 28814125] - Michael D Wunderli, Matthias Vonmoos, Lorena Treichler, Carmen Zeller, Isabel Dziobek, Thomas Kraemer, Markus R Baumgartner, Erich Seifritz, Boris B Quednow. Social Cognition and Interaction in Chronic Users of 3,4-Methylenedioxymethamphetamine (MDMA, 'Ecstasy').
The international journal of neuropsychopharmacology.
2018 04; 21(4):333-344. doi:
10.1093/ijnp/pyx098. [PMID: 29087534] - Anna Maria Górska, Katarzyna Kamińska, Agnieszka Wawrzczak-Bargieła, Giulia Costa, Micaela Morelli, Ryszard Przewłocki, Grzegorz Kreiner, Krystyna Gołembiowska. Neurochemical and Neurotoxic Effects of MDMA (Ecstasy) and Caffeine After Chronic Combined Administration in Mice.
Neurotoxicity research.
2018 04; 33(3):532-548. doi:
10.1007/s12640-017-9831-9. [PMID: 29134560] - Jakob A Shimshoni, Eyal Sobol, Ezekiel Golan, Yulius Ben Ari, Orit Gal. Pharmacokinetic and pharmacodynamic evaluation of 5-methoxy-2-aminoindane (MEAI): A new binge-mitigating agent.
Toxicology and applied pharmacology.
2018 03; 343(?):29-39. doi:
10.1016/j.taap.2018.02.009. [PMID: 29458138] - Patrick Vizeli, Henriette E Meyer Zu Schwabedissen, Matthias E Liechti. No major role of norepinephrine transporter gene variations in the cardiostimulant effects of MDMA.
European journal of clinical pharmacology.
2018 Mar; 74(3):275-283. doi:
10.1007/s00228-017-2392-2. [PMID: 29198060] - 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] - E Papaseit, M Torrens, C Pérez-Mañá, R Muga, M Farré. Key interindividual determinants in MDMA pharmacodynamics.
Expert opinion on drug metabolism & toxicology.
2018 Feb; 14(2):183-195. doi:
10.1080/17425255.2018.1424832. [PMID: 29303006] - K P C Kuypers, R de la Torre, M Farre, N Pizarro, L Xicota, J G Ramaekers. MDMA-induced indifference to negative sounds is mediated by the 5-HT2A receptor.
Psychopharmacology.
2018 02; 235(2):481-490. doi:
10.1007/s00213-017-4699-1. [PMID: 28735368] - K P C Kuypers, R de la Torre, M Farre, L Xicota, E B de Sousa Fernandes Perna, E L Theunissen, J G Ramaekers. Depressive mood ratings are reduced by MDMA in female polydrug ecstasy users homozygous for the l-allele of the serotonin transporter.
Scientific reports.
2018 01; 8(1):1061. doi:
10.1038/s41598-018-19618-1. [PMID: 29348651] - Shizhuang Weng, Ronglu Dong, Zede Zhu, Dongyan Zhang, Jinling Zhao, Linsheng Huang, Dong Liang. Dynamic surface-enhanced Raman spectroscopy and Chemometric methods for fast detection and intelligent identification of methamphetamine and 3, 4-Methylenedioxy methamphetamine in human urine.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2018 Jan; 189(?):1-7. doi:
10.1016/j.saa.2017.08.004. [PMID: 28783586] - Daniel W Curry, Matthew B Young, Andrew N Tran, Georges E Daoud, Leonard L Howell. Separating the agony from ecstasy: R(-)-3,4-methylenedioxymethamphetamine has prosocial and therapeutic-like effects without signs of neurotoxicity in mice.
Neuropharmacology.
2018 Jan; 128(?):196-206. doi:
10.1016/j.neuropharm.2017.10.003. [PMID: 28993129] - Linda D Simmler, Matthias E Liechti. Pharmacology of MDMA- and Amphetamine-Like New Psychoactive Substances.
Handbook of experimental pharmacology.
2018 ; 252(?):143-164. doi:
10.1007/164_2018_113. [PMID: 29633178] - Patrick Vizeli, Matthias E Liechti. Oxytocin receptor gene variations and socio-emotional effects of MDMA: A pooled analysis of controlled studies in healthy subjects.
PloS one.
2018; 13(6):e0199384. doi:
10.1371/journal.pone.0199384. [PMID: 29912955] - Ravieh Golchoobian, Fatemeh Nabavizadeh, Mehrdad Roghani, Alireza Foroumadi, Maryam Mohammadian. Ghrelin Alleviates MDMA-Induced Disturbance of Serum Glucose and Lipids Levels in the Rat.
Acta medica Iranica.
2017 Dec; 55(12):736-743. doi:
NULL. [PMID: 29373879] - Anne Zwartsen, Anouk H A Verboven, Regina G D M van Kleef, Fiona M J Wijnolts, Remco H S Westerink, Laura Hondebrink. Measuring inhibition of monoamine reuptake transporters by new psychoactive substances (NPS) in real-time using a high-throughput, fluorescence-based assay.
Toxicology in vitro : an international journal published in association with BIBRA.
2017 Dec; 45(Pt 1):60-71. doi:
10.1016/j.tiv.2017.05.010. [PMID: 28506818] - Alireza Gharebaghi, Iraj Amiri, Iraj Salehi, Siamak Shahidi, Alireza Komaki, Mehdi Mehdizadeh, Fahimeh Ghasemi Moravej, Sara Soleimani Asl. Treadmill exercise attenuates 3,4-methylenedioxymethamphetamine-induced memory impairment through a decrease apoptosis in male rat hippocampus.
Journal of neuroscience research.
2017 12; 95(12):2448-2455. doi:
10.1002/jnr.24078. [PMID: 28493333] - Giulia Costa, Micaela Morelli, Nicola Simola. Progression and Persistence of Neurotoxicity Induced by MDMA in Dopaminergic Regions of the Mouse Brain and Association with Noradrenergic, GABAergic, and Serotonergic Damage.
Neurotoxicity research.
2017 Nov; 32(4):563-574. doi:
10.1007/s12640-017-9761-6. [PMID: 28597409] - Isabel Gomila, Concepción Moranta, Loreto Quesada, Yolanda Pastor, Macarena Dastis, Albert Torrents, Miguel Ángel Elorza, Francesco Paolo Busardò, Bernardino Barceló. Cross-reactivity of selected benzofurans with commercial amphetamine and ecstasy immunoassays in urine.
Bioanalysis.
2017 Nov; 9(22):1771-1785. doi:
10.4155/bio-2017-0191. [PMID: 28975809] - Matthew B Young, Seth D Norrholm, Lara M Khoury, Tanja Jovanovic, Sheila A M Rauch, Collin M Reiff, Boadie W Dunlop, Barbara O Rothbaum, Leonard L Howell. Inhibition of serotonin transporters disrupts the enhancement of fear memory extinction by 3,4-methylenedioxymethamphetamine (MDMA).
Psychopharmacology.
2017 Oct; 234(19):2883-2895. doi:
10.1007/s00213-017-4684-8. [PMID: 28741031] - Bardia Jamali, Behjat Sheikholeslami, Yalda Hosseinzadeh Ardakani, Hoda Lavasani, Mohammad-Reza Rouini. Evaluation of the Ecstasy influence on tramadol and its main metabolite plasma concentration in rats.
Drug metabolism and personalized therapy.
2017 09; 32(3):137-145. doi:
10.1515/dmpt-2017-0018. [PMID: 28917081] - Lilian H J Richter, Veit Flockerzi, Hans H Maurer, Markus R Meyer. Pooled human liver preparations, HepaRG, or HepG2 cell lines for metabolism studies of new psychoactive substances? A study using MDMA, MDBD, butylone, MDPPP, MDPV, MDPB, 5-MAPB, and 5-API as examples.
Journal of pharmaceutical and biomedical analysis.
2017 Sep; 143(?):32-42. doi:
10.1016/j.jpba.2017.05.028. [PMID: 28601767] - Martina I Boxler, Matthias E Liechti, Yasmin Schmid, Thomas Kraemer, Andrea E Steuer. First Time View on Human Metabolome Changes after a Single Intake of 3,4-Methylenedioxymethamphetamine in Healthy Placebo-Controlled Subjects.
Journal of proteome research.
2017 09; 16(9):3310-3320. doi:
10.1021/acs.jproteome.7b00294. [PMID: 28722422] - M E Mothibe, E Osuch, C P Kahler-Venter. Commercial herbal medicines used as African traditional medicines: Ngoma Herbal Tonic Immune Booster interferes with a rapid urine drug screening test.
South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde.
2017 08; 107(9):734-737. doi:
10.7196/samj.2017.v107i9.12197. [PMID: 28875876] - Alberto Salomone, Joseph J Palamar, Enrico Gerace, Daniele Di Corcia, Marco Vincenti. Hair Testing for Drugs of Abuse and New Psychoactive Substances in a High-Risk Population.
Journal of analytical toxicology.
2017 Jun; 41(5):376-381. doi:
10.1093/jat/bkx020. [PMID: 28334805] - Iria González-Mariño, Ettore Zuccato, Miquel M Santos, Sara Castiglioni. Monitoring MDMA metabolites in urban wastewater as novel biomarkers of consumption.
Water research.
2017 05; 115(?):1-8. doi:
10.1016/j.watres.2017.01.063. [PMID: 28254532] - Mercedes Pérez-Hernández, María Encarnación Fernández-Valle, Ana Rubio-Araiz, Rebeca Vidal, María Dolores Gutiérrez-López, Esther O'Shea, María Isabel Colado. 3,4-Methylenedioxymethamphetamine (MDMA, ecstasy) produces edema due to BBB disruption induced by MMP-9 activation in rat hippocampus.
Neuropharmacology.
2017 05; 118(?):157-166. doi:
10.1016/j.neuropharm.2017.03.019. [PMID: 28322979] - Patrick Vizeli, Matthias E Liechti. Safety pharmacology of acute MDMA administration in healthy subjects.
Journal of psychopharmacology (Oxford, England).
2017 05; 31(5):576-588. doi:
10.1177/0269881117691569. [PMID: 28443695] - Kim P C Kuypers, Patrick C Dolder, Johannes G Ramaekers, Matthias E Liechti. Multifaceted empathy of healthy volunteers after single doses of MDMA: A pooled sample of placebo-controlled studies.
Journal of psychopharmacology (Oxford, England).
2017 05; 31(5):589-598. doi:
10.1177/0269881117699617. [PMID: 28372480] - Arani Nanavati, Leal C Herlitz. Tubulointerstitial Injury and Drugs of Abuse.
Advances in chronic kidney disease.
2017 03; 24(2):80-85. doi:
10.1053/j.ackd.2016.09.008. [PMID: 28284383] - 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]