Mephedrone (BioDeep_00000017868)

 

Secondary id: BioDeep_00000397521, BioDeep_00000408408

human metabolite Chemicals and Drugs


代谢物信息卡片


2-(methylamino)-1-(4-methylphenyl)propan-1-one

化学式: C11H15NO (177.115358)
中文名称: 2-(甲基氨基)-1-(4-甲基苯基)-1-丙酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=CC=C(C=C1)C(=O)C(C)NC
InChI: InChI=1S/C11H15NO/c1-8-4-6-10(7-5-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3

描述信息

In 2010, unconfirmed reports speculated about the role mephedrone has played in the deaths of several young people in the UK. By July 2010, mephedrone had been alleged to be involved in 52 fatalities in the UK, but detected in only 38 of these cases. Of the nine that coroners had finished investigating, two were caused directly by mephedrone. The first death reported to be caused by mephedrone use was that of 46-year-old, John Sterling Smith, who had underlying health problems and repeatedly injected the drug. A report in Forensic Science International in August 2010 stated mephedrone intoxication has been recorded as the cause of death in two cases in Scotland. Post mortem samples showed the concentration of mephedrone in their blood was 22 mg/l in one case and 3.3 mg/l in the other. The death of a teenager in the UK in November 2009 was widely reported as being caused by mephedrone, but a report by the coroner concluded she had died from natural causes. In March 2010, the deaths of two teenagers in Scunthorpe were widely reported by the media to be caused by mephedrone. Toxicology reports showed the teenagers had not taken any mephedrone and had died as a result of consuming alcohol and the heroin substitute methadone. According to Fiona Measham, a criminologist who is a member of the ACMD, the reporting of the unconfirmed deaths by newspapers followed the usual cycle of exaggeration, distortion, inaccuracy and sensationalism associated with the reporting of recreational drug use. Mephedrone is a white substance. It is sold most commonly as crystals or a powder, but also in the form of capsules or pills. It can have a distinctive odour, reported to range from a synthetic fishy smell to the smell of vanilla and bleach, stale urine, or electric circuit boards. Mephedrone is one of hundreds of designer drugs or legal highs that have been reported in recent years, including artificial chemicals such as synthetic cannabis and semisynthetic substances such as methylhexaneamine. These drugs are primarily developed to avoid being controlled by laws against illegal drugs, thus giving them the label of designer drugs. According to the European Monitoring Centre for Drugs and Drug Addiction, the synthesis of mephedrone was first reported in 1929 by Saem de Burnaga Sanchez in the Bulletin de la Societe Chimique de France, under the name toluyl-alpha-monomethylaminoethylcetone,:17 but the compound remained an obscure product of academia until 2003, when it was re-discovered and publicised by an underground chemist on The Hive website, working under the pseudonym Kinetic. Mephedrone, also known as 4-methylmethcathinone (4-MMC), or 4-methylephedrone, is a synthetic stimulant drug of the amphetamine and cathinone classes. Slang names include meph, drone, MCAT, meow meow, and bubble. It is reportedly manufactured in China and is chemically similar to the cathinone compounds found in the khat plant of eastern Africa. It comes in the form of tablets or a powder, which users can swallow, snort or inject, producing similar effects to MDMA, amphetamines, and cocaine.

同义名列表

9 个代谢物同义名

2-(methylamino)-1-(4-methylphenyl)propan-1-one; beta-Keto-4-methylmethamphetamine; BK-4-Methylmethamphetamine; 4-Methylmethcathinone; 4-Methylephedrone; 4-MMC Compound; MMCAT compound; mephedrone; 4-MMC



数据库引用编号

10 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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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

  • Joanna Czerwinska, Mark C Parkin, Claire George, Andrew T Kicman, Paul I Dargan, Vincenzo Abbate. Excretion of mephedrone and its phase I metabolites in urine after a controlled intranasal administration to healthy human volunteers. Drug testing and analysis. 2022 Apr; 14(4):741-746. doi: 10.1002/dta.3214. [PMID: 34984836]
  • Georgios Christos Papaioannou, Sophia Karastogianni, Stella Girousi. Development of an Electrochemical Sensor Using a Modified Carbon Paste Electrode with Silver Nanoparticles Capped with Saffron for Monitoring Mephedrone. Sensors (Basel, Switzerland). 2022 Feb; 22(4):. doi: 10.3390/s22041625. [PMID: 35214527]
  • Julie A Marusich, Elaine A Gay, Delisha A Stewart, Bruce E Blough. Sex differences in inflammatory cytokine levels following synthetic cathinone self-administration in rats. Neurotoxicology. 2022 01; 88(?):65-78. doi: 10.1016/j.neuro.2021.11.002. [PMID: 34742947]
  • Courtney Gearlds, Jessica Brooke Bouldin, Mariah McKinney, Shannon Schreiner, Stacy D Brown, Brooks B Pond. Pharmacokinetics of Synthetic Cathinones Found in Bath Salts in Mouse Brain and Plasma Using High-Pressure Liquid Chromatography-Tandem Mass Spectrometry. European journal of drug metabolism and pharmacokinetics. 2021 Nov; 46(6):771-778. doi: 10.1007/s13318-021-00712-1. [PMID: 34427910]
  • Joanna Czerwinska, Mark C Parkin, Claire George, Andrew T Kicman, Paul I Dargan, Vincenzo Abbate. Pharmacokinetics of Mephedrone and Its Metabolites in Whole Blood and Plasma after Controlled Intranasal Administration to Healthy Human Volunteers. Journal of analytical toxicology. 2021 Aug; 45(7):730-738. doi: 10.1093/jat/bkaa134. [PMID: 32986113]
  • Sarah L Belsey, Robert J Flanagan. Analytical Detection of Novel Stimulants by Immunoassay and Liquid Chromatography-High Resolution Mass Spectrometry: Case Studies on Ethylphenidate and Mephedrone. Journal of analytical toxicology. 2021 May; 45(5):521-528. doi: 10.1093/jat/bkaa102. [PMID: 32816012]
  • Eulalia Olesti, Jose Antonio Pascual, Mireia Ventura, Esther Papaseit, Magí Farré, Rafael de la Torre, Oscar J Pozo. LC-MS/MS method for the quantification of new psychoactive substances and evaluation of their urinary detection in humans for doping control analysis. Drug testing and analysis. 2020 Jun; 12(6):785-797. doi: 10.1002/dta.2768. [PMID: 31950617]
  • L Anzillotti, L Calò, A Banchini, M L Schirripa, F Marezza, R Cecchi. Mephedrone and chemsex: a case report. Legal medicine (Tokyo, Japan). 2020 Feb; 42(?):101640. doi: 10.1016/j.legalmed.2019.101640. [PMID: 31751794]
  • Eulàlia Olesti, Magí Farré, Marcel Lí Carbó, Esther Papaseit, Clara Perez-Mañá, Marta Torrens, Samanta Yubero-Lahoz, Mitona Pujadas, Óscar J Pozo, Rafael de la Torre. Dose-Response Pharmacological Study of Mephedrone and Its Metabolites: Pharmacokinetics, Serotoninergic Effects, and Impact of CYP2D6 Genetic Variation. Clinical pharmacology and therapeutics. 2019 09; 106(3):596-604. doi: 10.1002/cpt.1417. [PMID: 30815856]
  • Albert Pérez-Alcaraz, Francesc Borrull, Carme Aguilar, Marta Calull. Enantioselective determination of cathinones in urine by high pressure in-line SPE-CE. Electrophoresis. 2019 07; 40(14):1762-1770. doi: 10.1002/elps.201900072. [PMID: 31093983]
  • Diane M Calinski, David F Kisor, Jon E Sprague. A review of the influence of functional group modifications to the core scaffold of synthetic cathinones on drug pharmacokinetics. Psychopharmacology. 2019 Mar; 236(3):881-890. doi: 10.1007/s00213-018-4985-6. [PMID: 30069588]
  • 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]
  • Hao-Hsin Wu, Yi-Ting Shen, Chien-Shun Chiou, Chi-Tai Fang, Yi-Chun Lo. Shigellosis outbreak among MSM living with HIV: a case-control study in Taiwan, 2015-2016. Sexually transmitted infections. 2019 02; 95(1):67-70. doi: 10.1136/sextrans-2017-053410. [PMID: 29535222]
  • Felix P Mayer, Diethart Schmid, Marion Holy, Lynette C Daws, Harald H Sitte. "Polytox" synthetic cathinone abuse: A potential role for organic cation transporter 3 in combined cathinone-induced efflux. Neurochemistry international. 2019 02; 123(?):7-12. doi: 10.1016/j.neuint.2018.09.008. [PMID: 30248432]
  • 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]
  • Piotr Tarkowski, Krzysztof Jankowski, Barbara Budzyńska, Grażyna Biała, Anna Boguszewska-Czubara. Potential pro-oxidative effects of single dose of mephedrone in vital organs of mice. Pharmacological reports : PR. 2018 Dec; 70(6):1097-1104. doi: 10.1016/j.pharep.2018.05.010. [PMID: 30308460]
  • Rajan Patel, Neha Maurya, Mehraj Ud Din Parray, Nida Farooq, Abrar Siddique, Kanak Lata Verma, Neeraj Dohare. Esterase activity and conformational changes of bovine serum albumin toward interaction with mephedrone: Spectroscopic and computational studies. Journal of molecular recognition : JMR. 2018 11; 31(11):e2734. doi: 10.1002/jmr.2734. [PMID: 29920814]
  • Steven J Simmons, Jonna M Leyrer-Jackson, Chicora F Oliver, Callum Hicks, John W Muschamp, Scott M Rawls, M Foster Olive. DARK Classics in Chemical Neuroscience: Cathinone-Derived Psychostimulants. ACS chemical neuroscience. 2018 10; 9(10):2379-2394. doi: 10.1021/acschemneuro.8b00147. [PMID: 29714473]
  • 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]
  • John H Anneken, Mariana Angoa-Perez, Girish C Sati, David Crich, Donald M Kuhn. Assessing the role of dopamine in the differential neurotoxicity patterns of methamphetamine, mephedrone, methcathinone and 4-methylmethamphetamine. Neuropharmacology. 2018 05; 134(Pt A):46-56. doi: 10.1016/j.neuropharm.2017.08.033. [PMID: 28851615]
  • Dino Luethi, Karolina E Kolaczynska, Luca Docci, Stephan Krähenbühl, Marius C Hoener, Matthias E Liechti. Pharmacological profile of mephedrone analogs and related new psychoactive substances. Neuropharmacology. 2018 05; 134(Pt A):4-12. doi: 10.1016/j.neuropharm.2017.07.026. [PMID: 28755886]
  • Erika Castrignanò, Marie Mardal, Axel Rydevik, Bram Miserez, John Ramsey, Trevor Shine, G Dan Pantoș, Markus R Meyer, Barbara Kasprzyk-Hordern. A new approach towards biomarker selection in estimation of human exposure to chiral chemicals: a case study of mephedrone. Scientific reports. 2017 11; 7(1):13009. doi: 10.1038/s41598-017-12581-3. [PMID: 29097766]
  • Eulàlia Olesti, Magí Farré, Esther Papaseit, Aristotelis Krotonoulas, Mitona Pujadas, Rafael de la Torre, Óscar J Pozo. Pharmacokinetics of Mephedrone and Its Metabolites in Human by LC-MS/MS. The AAPS journal. 2017 11; 19(6):1767-1778. doi: 10.1208/s12248-017-0132-2. [PMID: 28828691]
  • 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]
  • Listos Joanna, Talarek Sylwia, Gryzinska Magdalena, Listos Piotr, Kedzierska Ewa, Orzelska-Gorka Jolanta, Dylewska Malgorzata, Lupina Malgorzata, Jolanta H Kotlinska. Mephedrone exposure in adolescent rats alters the rewarding effect of morphine in adults. European journal of pharmacology. 2017 Sep; 810(?):63-69. doi: 10.1016/j.ejphar.2017.06.007. [PMID: 28603042]
  • Lauren G Strange, Kerri Kochelek, Robert Keasling, Stacy D Brown, Brooks B Pond. The pharmacokinetic profile of synthetic cathinones in a pregnancy model. Neurotoxicology and teratology. 2017 Sep; 63(?):9-13. doi: 10.1016/j.ntt.2017.08.001. [PMID: 28811141]
  • Alyssa F DeLarge, Laura L Erwin, Peter J Winsauer. Atypical binding at dopamine and serotonin transporters contribute to the discriminative stimulus effects of mephedrone. Neuropharmacology. 2017 06; 119(?):62-75. doi: 10.1016/j.neuropharm.2017.04.006. [PMID: 28396142]
  • Eulàlia Olesti, Mitona Pujadas, Esther Papaseit, Clara Pérez-Mañá, Óscar J Pozo, Magí Farré, Rafael de la Torre. GC-MS Quantification Method for Mephedrone in Plasma and Urine: Application to Human Pharmacokinetics. Journal of analytical toxicology. 2017 Mar; 41(2):100-106. doi: 10.1093/jat/bkw120. [PMID: 27798075]
  • Gavin McLaughlin, Noreen Morris, Pierce V Kavanagh, John D Power, Geraldine Dowling, Brendan Twamley, John O'Brien, Brian Talbot, Donna Walther, John S Partilla, Michael H Baumann, Simon D Brandt. Synthesis, characterization and monoamine transporter activity of the new psychoactive substance mexedrone and its N-methoxy positional isomer, N-methoxymephedrone. Drug testing and analysis. 2017 Mar; 9(3):358-368. doi: 10.1002/dta.2053. [PMID: 27524685]
  • S Stevens Negus, Matthew L Banks. Decoding the Structure of Abuse Potential for New Psychoactive Substances: Structure-Activity Relationships for Abuse-Related Effects of 4-Substituted Methcathinone Analogs. Current topics in behavioral neurosciences. 2017; 32(?):119-131. doi: 10.1007/7854_2016_18. [PMID: 27696217]
  • Mariana Angoa-Pérez, John H Anneken, Donald M Kuhn. Neurotoxicology of Synthetic Cathinone Analogs. Current topics in behavioral neurosciences. 2017 ; 32(?):209-230. doi: 10.1007/7854_2016_21. [PMID: 27753008]
  • Esther Papaseit, Eulalia Olesti, Rafael de la Torre, Marta Torrens, Magi Farre. Mephedrone Concentrations in Cases of Clinical Intoxication. Current pharmaceutical design. 2017; 23(36):5511-5522. doi: 10.2174/1381612823666170704130213. [PMID: 28677506]
  • Pascal Kintz. Evidence of 2 Populations of Mephedrone Abusers by Hair Testing. Application to 4 Forensic Expertises. Current neuropharmacology. 2017; 15(5):658-662. doi: 10.2174/1570159x14666161026152107. [PMID: 27784226]
  • Flaminia Pantano, Roberta Tittarelli, Giulio Mannocchi, Roberta Pacifici, Alessandro di Luca, Francesco Paolo Busardò, Enrico Marinelli. Neurotoxicity Induced by Mephedrone: An up-to-date Review. Current neuropharmacology. 2017; 15(5):738-749. doi: 10.2174/1570159x14666161130130718. [PMID: 27908258]
  • Bertha K Madras. The Growing Problem of New Psychoactive Substances (NPS). Current topics in behavioral neurosciences. 2017 ; 32(?):1-18. doi: 10.1007/7854_2016_34. [PMID: 27571747]
  • C Michael White. Mephedrone and 3,4-Methylenedioxypyrovalerone (MDPV): Synthetic Cathinones With Serious Health Implications. Journal of clinical pharmacology. 2016 11; 56(11):1319-1325. doi: 10.1002/jcph.742. [PMID: 27029951]
  • Esther Papaseit, Clara Pérez-Mañá, Julián-Andrés Mateus, Mitona Pujadas, Francina Fonseca, Marta Torrens, Eulàlia Olesti, Rafael de la Torre, Magí Farré. Human Pharmacology of Mephedrone in Comparison with MDMA. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2016 10; 41(11):2704-13. doi: 10.1038/npp.2016.75. [PMID: 27206266]
  • F P Mayer, L Wimmer, O Dillon-Carter, J S Partilla, N V Burchardt, M D Mihovilovic, M H Baumann, H H Sitte. Phase I metabolites of mephedrone display biological activity as substrates at monoamine transporters. British journal of pharmacology. 2016 09; 173(17):2657-68. doi: 10.1111/bph.13547. [PMID: 27391165]
  • Katarzyna Styszko, Agnieszka Dudarska, Dariusz Zuba. The Presence of Stimulant Drugs in Wastewater from Krakow (Poland): A Snapshot. Bulletin of environmental contamination and toxicology. 2016 Sep; 97(3):310-5. doi: 10.1007/s00128-016-1869-5. [PMID: 27365137]
  • Andrés Ciudad-Roberts, Leticia Duart-Castells, Jorge Camarasa, David Pubill, Elena Escubedo. The combination of ethanol with mephedrone increases the signs of neurotoxicity and impairs neurogenesis and learning in adolescent CD-1 mice. Toxicology and applied pharmacology. 2016 Feb; 293(?):10-20. doi: 10.1016/j.taap.2015.12.019. [PMID: 26747301]
  • Igor Linhart, Michal Himl, Monika Židková, Marie Balíková, Eva Lhotková, Tomáš Páleníček. Metabolic profile of mephedrone: Identification of nor-mephedrone conjugates with dicarboxylic acids as a new type of xenobiotic phase II metabolites. Toxicology letters. 2016 Jan; 240(1):114-21. doi: 10.1016/j.toxlet.2015.10.025. [PMID: 26541208]
  • 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]
  • Julie A Suyama, Farhana Sakloth, Renata Kolanos, Richard A Glennon, Matthew F Lazenka, S Stevens Negus, Matthew L Banks. Abuse-Related Neurochemical Effects of Para-Substituted Methcathinone Analogs in Rats: Microdialysis Studies of Nucleus Accumbens Dopamine and Serotonin. The Journal of pharmacology and experimental therapeutics. 2016 Jan; 356(1):182-90. doi: 10.1124/jpet.115.229559. [PMID: 26645638]
  • Raúl López-Arnau, José Martínez-Clemente, Teresa Rodrigo, David Pubill, Jorge Camarasa, Elena Escubedo. Neuronal changes and oxidative stress in adolescent rats after repeated exposure to mephedrone. Toxicology and applied pharmacology. 2015 Jul; 286(1):27-35. doi: 10.1016/j.taap.2015.03.015. [PMID: 25817894]
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