DOI:
https://doi.org/10.38017/1657463X.686Palavras-chave:
Catinona, Mefedrona, 4-metilmetcatinona, Farmacologia, ToxicologiaResumo
Nos últimos 25 anos na Europa, surgiram novas drogas sintéticas derivadas da planta khat (Catha edulis), obtidas do grupo Catinona. A catinona é um alcaloide muito potente análogo às anfetaminas. Entre os derivados da catinona está a mefedrona (4-metilmetcatinona (4-MMC)), que possui efeitos farmacológicos equivalentes aos relatados pelo ecstasy, anfetamina ou cocaína. O artigo apresenta uma revisão bibliográfica abrangente dos principais métodos de detecção da 4-MMC conhecida como mefedrona e sua metodologia de síntese, o artigo além disso mostra as propriedades físico-químicas, a farmacologia, a toxicologia e os principais efeitos nocivos sob a saúde. É de particular interesse e preocupação que esse medicamento derivado da efedrona seja proveniente de uma planta e seja considerado legal em alguns países da Europa Ocidental. Ele tem sido amplamente utilizado nos últimos anos para fins recreativos em vários países da Europa, América do Norte e na maioria dos países da América do Sul, devido à sua facilidade de compra e que se mostra como nova alternativa ao ecstasy e à cocaína. Os efeitos do 4-MMC estão associados aos efeitos dos estimulantes, como aumento da concentração, estimulação psicomotora, apetite reduzido e insônia. Estudos recentes descreveram que o uso compulsivo de mefedrona é principalmente um fenômeno juvenil e entre os efeitos colaterais perigosos estão o vício intenso, mudanças desconfortáveis na temperatura corporal e na frequência cardíaca, alucinações, psicose até a morte por overdose. Com base no exposto, é imprescindível que as revisões da literatura se concentrem na química, farmacologia, toxicologia e análise de risco para a mefedrona, para encontrar estratégias para determinação rápida e mitigar seus efeitos adversos em dependentes e evitar o consumo e favorecer em desenvolver metodologias de detecção.
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Referências
Adamowicz, P., Tokarczyk, B., Stanaszek, R., & Slopianka, M. 2013. Fatal mephedrone intoxication – cla case report. Journal of Analytical Toxicology (37): 37–42.
Adamowicz, P., Gieroń, J., Gil, D., Lechowicz, W., Skulska, A., & Tokarczyk, B. 2016a. The prevalence of new psychoactive substances in biological material - a three-year review of casework in Poland. Drug Test. Anal. 8 (1): 63−70.
Adamowicz, P., Gieroń, J., Gil, D., Lechowicz, W., Skulska, A., Tokarczyk, & B., Zuba, D. 2016b. Blood concentrations of α-pyrrolidinovalerophenone (α-PVP) determined in 66 forensic samples. Forensic Toxicol. (34): 227–234.
Adamowicz, P., & Malczyk, A., 2019. Stability of synthetic cathinones in blood and urine. Forensic Sci Int. 295, 36−45.
Anneken J. H, Angoa-Pérez M, & Kuhn D. M. 2015. 4-Methylenedioxypyrovalerone prevents while methylone enhances methamphetamine-induced damage to dopamine nerve endings: b-ketoamphetamine modulation of neurotoxicity by the dopamine transporter. Journal of Neurochemistry (113): 211–222.
Archer, R. 2009. Fluoromethcathinone, a new substance of abuse. Forensic Science International. (185): 10-20.
Bahuman, M. H., Ayestas, M. A., Partilla, J. S., Sink, J. R., Daley, P. F., Brandt, S. D., & Richard B Rothmanl. 2012. The Designer Methcathinone Analogs, Mephedrone and Methylone, are Substrates for Monoamine Transporters in Brain Tissue. Neuropsychopharmacology (37): 1192–1203.
Barrio, P., Gaskell, M., Goti, J., Vilardell, S., & Fàbregas, J. M. 2016. Persistent psychotic symptoms after long-term heavy use of mephedrone: A two-case series. adicciones 28 (3): 154-158.
Brandt, S., Sumnall, H., Measham, F., & Cole, J. 2016. Analyses of second-generation 'legal highs' in the UK: initial findings. Drug Testing and Analysis (37): 377-382.
Busardo, F. P., Kyriakou, C., Tittarelli, R., Mannocchi, G., Pantano , F., Santurro , A., & Baglı`o, G. 2015. Assessment of the stability of mephedrone in ante-mortem and post-mortem blood specimens. Forensic Science International (256): 28–37.
Camilleri, A., Johnston, M. R., Brennan, M., Davis, S., & Caldicott, D. G. 2010. Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine a-phthalimidopropiophenone and N-ethylcathinone. Forensic Science International (196): 59-66.
Carhart-Harrist, R. I., King, L. A., & Nut, D. J. 2011. A web-based survey on mephedrone. Drug and Alcohol Dependence (118): 19-22.
Christie, R., Horan, E, Fox, J., O'Donnell, C., Byrne, H.J., McDermott, Power, J. S.& Kavanagh, P. 2014. Discrimination of cathinone regioisomers, sold as 'legal highs', by
Raman spectroscopy, Drug Test Anal 6 (7-8): 651-657.
Dargan, P. L., Sedefov, R., Gallegos, A., & Wood, D. M. 2011. The pharmacology and toxicology of the synthetic cathinone mephedrone (4-methylmethcathinone). Drug Testing and Analysis, (3): 454-463.
Dick, D., & Torrance, C. 2010. Drugs Survey. MixMag (8): 225-244.
Dickson, A. J., Vorce, S. P., Levine, B., & Past, M. R. 2010. Multiple-drug toxicity caused by the coadministration of 4-methylmethcathinone (mephedrone) and heroin. Journal of Analytical Toxicology (34): 162–168.
EMCDDA. 2017. EMCDDA – Drug Profiles: Synthetic Cathinones. Available at: http://www.emcdda.europa.eu/publications/drug-profiles/synthetic-cathinones.
Eshleman, A., Wolfrum KM, Hatfield, M., Johnson, R., Murphy, K., & Janowsky, A. 2013. Substituted methcathinones differ in transporter and receptor interactions. Biochemical Pharmacology (85):
1803–1815.
EMCDDA. 2017. Report on the risk assessment of mefedrona in the framework of the Council Decision on new psychoactive substances. Berlin: Publications office of the European Union. Obtenido de http://www.emcdda.europa.eu/html.cfm/index116639EN.htm
EMCDDA. 2016. joint report on a new psychoactive substance: 4-methylmethcathinone (mephedrone). http://www.emcdda.europa.eu/attachements.cfm/att_102496_EN_Europol-EMCDDA_Joint_Report_Mephedrone.pdf, 1-3.
EWS: Early warning system. (2011). http://www.emcdda. europa.eu/themes/new-drugs/early-warning .
Ferreira, C., Vaz, A. R., Florindo, P. R., Lopes, Á., Brites, D., & Quintas, A. 2019. Development of a high throughput methodology to screen cathinones toxicological impact. Forensic Science International, (169): 1-9.
Fisher, D., Partridge, S. J., Handley, S. A., & Flanagan, R. J. 2013. Stability of some atypicalantipsychotics in human plasma, haemolysed whole blood, oral fluid, human serum and calf serum. Forensic Science International (229): 151–156.
Fleminng N. 2016. newscientist. Obtenido de Miaow-miaow on trial: truth or trumped-up charges?:ttp://www.newscientist.com/article/dn18712-miaowmiaow-on-trial-truth-or-trumpedup-charges.html,.
Freni, F., Bianco , S., Vignali, C., Groppi, A., Moretti, M., Marco, A. & Morini, L. 2019. A multi-analyte LC–MS/MS method for screening and quantification of 16 synthetic cathinones in hair: Application to postmortem cases. Forensic Science International, (298): 115-120.
Fukushima, S., Shen, H., Hata, H., Ohara, A., Ohmi, K., Ikeda, K. & Uhl, G. 2007. Methamphetamine-induced locomotor activity and sensitization in dopamine transporter and vesicular monoamine transporter 2 double mutant mice. Psychopharmacology (193): 55–62.
Gibbons, S. & Zloh, M. 2010. An analysis of the ‘legal high’ mephedrone. Bioorganic & Medicinal Chemistry Letters (20): 4135–4139.
Glickstein, S., & Schmauss, C. 2004. Effect of methamphetamine on cognition and repetitive motor behavior of mice deficient for dopamine D2 and D3 receptors. Annals of the New York Academy of Sciences (1025): 110–118.
Glicksberg, L. & Kerrigan, S. 2017. Stability of Synthetic Cathinones in Blood. J. Anal. Toxicol. (41): 711–719.
Glicksberg, L. & Kerrigan, S. 2018. Stability of Synthetic Cathinones in Urine. J. Anal. Toxicol. (42): 77–87.
Gygi, M., Gibb, J., & Hanson, G. 1996. Methcathinone: an initial study of its effects on monoaminergic systems. Journal of Pharmacology and Experimental Therapeutics (3): 1066–1072.
H. Torrance, 2010. The detection of mephedrone (4-methylmethcathinone) in 4 fatalities in Scotland. Forensic Science International,. (10): 62-63.
Jankovics, P., Varadi, A., Tolgyesi, L., Lohner, S., Nemeth-Palotas, J., & Koszegi-Szalai, H. 2012. Identification and characterization of the new designer drug 40-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography–tandem mass spectrometry (LC–MS/MS) screening method for seven different methcathinone analogs. Forensic Science International,(3): 213-220.
Jones, L., Reed, P., & Parrott, A. 2016. Mephedrone and 3,4-methylenedioxymethamphetamine: Comparative psychobiological effects as reported by recreational polydrug users. Journal of Psychopharmacology, 30 (12): 1313-1320.
Kapitány-Fövény, M., Kertész, M., Winstock, A., Deluca, P., & Corazza, O. 2013. Substitutional potential of mephedrone: an analysis of the subjective effects. Human Psychopharmacology: Clinical and Experimental (28): 308–316.
Kavanagh, P., O’Brien, J., Power, J. D., & Talbot, B. 2013. ‘Smoking’ mephedrone: The identification of the pyrolysis products of 4-methylmethcathinone hydrochloride. Drug Testing and Analysis (5):291–305.
Kehr, J., Ichinose, F., Yoshitake, S., Goiny, M., Sievertsson, T. & Nyberg, F. 2011. Mephedrone, compared to MDMA (ecstasy) and amphetamine, rapidly increases both dopamine and serotonin levels in nucleus accumbens of awake rats. British Journal of Pharmacology, 164 (8): 1949-1958.
Kelly J. P. 2011. Cathinone derivatives: A review of their chemistry, pharmacology and toxicology. Drug Testing and Analysis (3): 439-435.
Levitas, M.P., Andrews, E., Lurie, I., Marginean, I., 2018. Discrimination of synthetic cathinones by GC-MS and GC-MS/MS using cold electron ionization. Forensic Sci. Int. (288): 107–114.
Linharta, I., Himla, M., Židková, M., Balíková, M., Lhotkovác, E., & Pálenícek, T. 2016. Metabolic profile of mephedrone: Identification of nor-mephedrone conjugates with dicarboxylic acids as a new type of xenobiotic phase II Metabolites. Toxicology Letters, (204): 54.62.
Lisek, R., Xu, W., Yuvasheva, E., Chiu, Y., Reitz, A., Liu-Chen, L. & Rawls, S. 2014. Mephedrone (‘bath salt’) elicits conditioned place preference and dopaminesensitive motor activation. Drug and Alcohol Dependence, (3): 257-262.
López-Rabuñala, Á., Lendoiro, E., Concheiro, M., López-Rivadulla, M., Cruz, A., & de-Castro-Ríos, A. (2019). A LC-MS/MS method for the determination of common synthetic cathinones in meconium. Journal of Chromatography B, (5): 349-355.
Martinez-Clemente, J., Escubedo E, Pubill. & Camarasa. 2012. nteraction of mephedrone with dopamine and serotonin targets in rats. European Neuropsychopharmacology 3 (22): 231-236.
Martınez-Clemente, J., Lopez-Arnau, R., Abad, S., Pubill, D., Escubedo, E., & Camarasa, J. 2014. Dose and Time-Dependent Selective Neurotoxicity Induced by Mephedrone in Mice. Plos One (50): 1-11.
Mercieca, G., Odoardi, S., Cassar, M., & Strano Rossi, S. (2018). Rapid and simple procedure for the determination of cathinones, amphetamine-like stimulants and other new psychoactive substances in blood and urine by GC–MS. Journal of Pharmaceutical and Biomedical Analysis, (149): 494-501.
Meyer, M. R., Wilhelm, J., Peters, F. T. & Maurer, H. H. 2013. Beta-keto amphetamines: studies on the metabolism of the designer drug mephedrone and toxicological detection of mephedrone, butylone, and methylone in urine using gas chromatography-mass spectrometry. Analytical and Bioanalytical Chemistry 3 (397): 1225-1233.
Meyer M. R & Maurer H. H. 2010. Metabolism of designer drugs of abuse: an updated review. Current Drug Metabolism 11 (5): 468-482.
Mori, T., Ito, S., Kita, T. & Sawaguchi, T. 2007. Effects of dopamine- and serotoninrelated compounds on methamphetamine-induced self-injurious behavior in mice. Journal of Pharmacological Sciences (96): 459–464.
Newman, J., He, W., & Verdin, E. 2012. Mitochondrial protein acylation and intermediary metabolism: regulation by sirtuins and implications for metabolic disease. Journal of Biological Chemistry (287): 42436–42443.
Pedersen, L., Johansen, S. S. & Linnet, K. 2015. In vitro metabolism studies on mephedrone and analysis of forensic cases. Drug Testing and Analysis, (1): 3-6.
Power M. 2010. How mephedrone shook the drug trade. Obtenido de http://www.drugscope.org.uk/Resources/Drugscope/Documents/PDF/Good%20Practice/DruglinkJanFeb10.pdf,
Power, J. D., Kavanagh, P., McLaughlin, G., O’Brien, J., Talbot, B., Barry, M. & Brandt, S. D. 2015. Identification and characterization of an imidazolium by-product formed during the synthesis of 4-methylmethcathinone (mephedrone). Drug Testing and Analysis (7): 894-902.
Power, P. McGlynn, K. Clarke, S.D. McDermott, P. Kavanagh & J. O'Brien (2011), The analysis of substituted cathinones. Part 1: chemical analysis of 2-, 3- and 4-methylmethcathinone, Forensic Sci Int 212(1-3): 6-12.
Pozo, O., Ibáñez, M., Sancho, J., Lahoz-Beneyetez, J. & Papaseit, M. 2015. Mass spectrometric evaluation of mephedrone in vivo human metabolism: identification of phase I and phase II metabolites including a novel succinyl conjugate. Drug Metabolism and Disposition (43): 248–257.
Razavipanah, I., Alipour, E., Deiminiat, B., & Hossein Rounaghi, G. 2018. A novel electrochemical imprinted sensor for ultrasensitive detection of the new psychoactive substance “Mephedrone”. Biosensors and Bioelectronics, (119): 163-169.
Schifano, F., Albanese, A., Fergus, S., Stair, J. L., Deluca, P., Corazza, O. & Ghods, H. 2011. Mephedrone (4-methylmethcathinone; ‘meow meow’): chemical, pharmacological and clinical issues. Psychopharmacology (214): 593-602.
Shortall, Spicer, C., Ebling, F., Green, A., Fone, K. & King, N. 2016. Contribution of serotonin and dopamine to changes in core body temperature and locomotor activity in rats following repeated administration of mephedrone. Addiction Biology (21): 1127–1139.
Simmler L. D 2013. Pharmacological characterization of designer cathinones in vitro. British Journal of Pharmacology (168): 458–470.
Sparago, M., Wlos J, Yuan J, Hatzidimitriou G, Tolliver J, & Dal Cason, T. A. 2001. Neurotoxic and pharmacologic studies on enantiomers of the N-methylated analog of cathinone (methcathinone): a new drug of abuse. Journal of Pharmacology and Experimental Therapeutics (279): 1043–1052.
Strano Rossi, S., Odoardi, S., Gregori, A., Peluso, G., Ripani, L., Ortar G., Serpelloni,G. & Romolo, F.S, 2014 An analytical approach to the forensic identification of different classes of new psychoactive substances (NPSs) in seized materials, Rapid Commun Mass Spectrom 28(17): 1904-1916.
Swortwood, M.J., Boland, D.M. & DeCaprio, A.P., 2013. Determination of 32 cathinone derivatives and other designer drugs in serum by comprehensive LC-Q-MS/MS analysis. Anal. Bioanal. Chem. 405 (4): 1383–1397.
Torrance, G. C. 2010. The detection of mephedrone (4-methylmethcathinone) in 4 fatalities in Scotland. Forensic Science International (13): 62-63.
Vardakou, I., Pistos, C., & Spiliopoulou, C. 2011. Drugs for youth via Internet and the example of mephedrone. Toxicology Letters (211): 191-195.
Winstock, A., Mitcheson, L., & Marsden, J. 2010. Mephedrone: still available and twice the price. The Lancet, (9752): 376-1537.
Winstock, A. R., Mitcheson, L. R., Deluca, P., Davey, Z., Corazza, O., & Schifano, F. 2010. Mephedrone, new kid for the chop? Addiction (106): 154–161.
Wood, D. M., Susannah, D., Puchnarewicz, M., Button, J., Archer, R., Ovaska, H. & Dargan, P. I. 2017. Recreational Use of Mephedrone (4-Methylmethcathinone, 4-MMC) with Associated Sympathomimetic Toxicity. Journal of Medical Toxicology (6): 327-330.
Zuba, D. & Adamowicz, P. 2016 Distinction of constitutional isomers of mephedrone by chromatographic and spectrometric methods, Aust J Forensic Sci 49(6): 1-13.
Adamowicz, P., Gieroń, J., Gil, D., Lechowicz, W., Skulska, A., & Tokarczyk, B. 2016a. The prevalence of new psychoactive substances in biological material - a three-year review of casework in Poland. Drug Test. Anal. 8 (1): 63−70.
Adamowicz, P., Gieroń, J., Gil, D., Lechowicz, W., Skulska, A., Tokarczyk, & B., Zuba, D. 2016b. Blood concentrations of α-pyrrolidinovalerophenone (α-PVP) determined in 66 forensic samples. Forensic Toxicol. (34): 227–234.
Adamowicz, P., & Malczyk, A., 2019. Stability of synthetic cathinones in blood and urine. Forensic Sci Int. 295, 36−45.
Anneken J. H, Angoa-Pérez M, & Kuhn D. M. 2015. 4-Methylenedioxypyrovalerone prevents while methylone enhances methamphetamine-induced damage to dopamine nerve endings: b-ketoamphetamine modulation of neurotoxicity by the dopamine transporter. Journal of Neurochemistry (113): 211–222.
Archer, R. 2009. Fluoromethcathinone, a new substance of abuse. Forensic Science International. (185): 10-20.
Bahuman, M. H., Ayestas, M. A., Partilla, J. S., Sink, J. R., Daley, P. F., Brandt, S. D., & Richard B Rothmanl. 2012. The Designer Methcathinone Analogs, Mephedrone and Methylone, are Substrates for Monoamine Transporters in Brain Tissue. Neuropsychopharmacology (37): 1192–1203.
Barrio, P., Gaskell, M., Goti, J., Vilardell, S., & Fàbregas, J. M. 2016. Persistent psychotic symptoms after long-term heavy use of mephedrone: A two-case series. adicciones 28 (3): 154-158.
Brandt, S., Sumnall, H., Measham, F., & Cole, J. 2016. Analyses of second-generation 'legal highs' in the UK: initial findings. Drug Testing and Analysis (37): 377-382.
Busardo, F. P., Kyriakou, C., Tittarelli, R., Mannocchi, G., Pantano , F., Santurro , A., & Baglı`o, G. 2015. Assessment of the stability of mephedrone in ante-mortem and post-mortem blood specimens. Forensic Science International (256): 28–37.
Camilleri, A., Johnston, M. R., Brennan, M., Davis, S., & Caldicott, D. G. 2010. Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine a-phthalimidopropiophenone and N-ethylcathinone. Forensic Science International (196): 59-66.
Carhart-Harrist, R. I., King, L. A., & Nut, D. J. 2011. A web-based survey on mephedrone. Drug and Alcohol Dependence (118): 19-22.
Christie, R., Horan, E, Fox, J., O'Donnell, C., Byrne, H.J., McDermott, Power, J. S.& Kavanagh, P. 2014. Discrimination of cathinone regioisomers, sold as 'legal highs', by
Raman spectroscopy, Drug Test Anal 6 (7-8): 651-657.
Dargan, P. L., Sedefov, R., Gallegos, A., & Wood, D. M. 2011. The pharmacology and toxicology of the synthetic cathinone mephedrone (4-methylmethcathinone). Drug Testing and Analysis, (3): 454-463.
Dick, D., & Torrance, C. 2010. Drugs Survey. MixMag (8): 225-244.
Dickson, A. J., Vorce, S. P., Levine, B., & Past, M. R. 2010. Multiple-drug toxicity caused by the coadministration of 4-methylmethcathinone (mephedrone) and heroin. Journal of Analytical Toxicology (34): 162–168.
EMCDDA. 2017. EMCDDA – Drug Profiles: Synthetic Cathinones. Available at: http://www.emcdda.europa.eu/publications/drug-profiles/synthetic-cathinones.
Eshleman, A., Wolfrum KM, Hatfield, M., Johnson, R., Murphy, K., & Janowsky, A. 2013. Substituted methcathinones differ in transporter and receptor interactions. Biochemical Pharmacology (85):
1803–1815.
EMCDDA. 2017. Report on the risk assessment of mefedrona in the framework of the Council Decision on new psychoactive substances. Berlin: Publications office of the European Union. Obtenido de http://www.emcdda.europa.eu/html.cfm/index116639EN.htm
EMCDDA. 2016. joint report on a new psychoactive substance: 4-methylmethcathinone (mephedrone). http://www.emcdda.europa.eu/attachements.cfm/att_102496_EN_Europol-EMCDDA_Joint_Report_Mephedrone.pdf, 1-3.
EWS: Early warning system. (2011). http://www.emcdda. europa.eu/themes/new-drugs/early-warning .
Ferreira, C., Vaz, A. R., Florindo, P. R., Lopes, Á., Brites, D., & Quintas, A. 2019. Development of a high throughput methodology to screen cathinones toxicological impact. Forensic Science International, (169): 1-9.
Fisher, D., Partridge, S. J., Handley, S. A., & Flanagan, R. J. 2013. Stability of some atypicalantipsychotics in human plasma, haemolysed whole blood, oral fluid, human serum and calf serum. Forensic Science International (229): 151–156.
Fleminng N. 2016. newscientist. Obtenido de Miaow-miaow on trial: truth or trumped-up charges?:ttp://www.newscientist.com/article/dn18712-miaowmiaow-on-trial-truth-or-trumpedup-charges.html,.
Freni, F., Bianco , S., Vignali, C., Groppi, A., Moretti, M., Marco, A. & Morini, L. 2019. A multi-analyte LC–MS/MS method for screening and quantification of 16 synthetic cathinones in hair: Application to postmortem cases. Forensic Science International, (298): 115-120.
Fukushima, S., Shen, H., Hata, H., Ohara, A., Ohmi, K., Ikeda, K. & Uhl, G. 2007. Methamphetamine-induced locomotor activity and sensitization in dopamine transporter and vesicular monoamine transporter 2 double mutant mice. Psychopharmacology (193): 55–62.
Gibbons, S. & Zloh, M. 2010. An analysis of the ‘legal high’ mephedrone. Bioorganic & Medicinal Chemistry Letters (20): 4135–4139.
Glickstein, S., & Schmauss, C. 2004. Effect of methamphetamine on cognition and repetitive motor behavior of mice deficient for dopamine D2 and D3 receptors. Annals of the New York Academy of Sciences (1025): 110–118.
Glicksberg, L. & Kerrigan, S. 2017. Stability of Synthetic Cathinones in Blood. J. Anal. Toxicol. (41): 711–719.
Glicksberg, L. & Kerrigan, S. 2018. Stability of Synthetic Cathinones in Urine. J. Anal. Toxicol. (42): 77–87.
Gygi, M., Gibb, J., & Hanson, G. 1996. Methcathinone: an initial study of its effects on monoaminergic systems. Journal of Pharmacology and Experimental Therapeutics (3): 1066–1072.
H. Torrance, 2010. The detection of mephedrone (4-methylmethcathinone) in 4 fatalities in Scotland. Forensic Science International,. (10): 62-63.
Jankovics, P., Varadi, A., Tolgyesi, L., Lohner, S., Nemeth-Palotas, J., & Koszegi-Szalai, H. 2012. Identification and characterization of the new designer drug 40-methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography–tandem mass spectrometry (LC–MS/MS) screening method for seven different methcathinone analogs. Forensic Science International,(3): 213-220.
Jones, L., Reed, P., & Parrott, A. 2016. Mephedrone and 3,4-methylenedioxymethamphetamine: Comparative psychobiological effects as reported by recreational polydrug users. Journal of Psychopharmacology, 30 (12): 1313-1320.
Kapitány-Fövény, M., Kertész, M., Winstock, A., Deluca, P., & Corazza, O. 2013. Substitutional potential of mephedrone: an analysis of the subjective effects. Human Psychopharmacology: Clinical and Experimental (28): 308–316.
Kavanagh, P., O’Brien, J., Power, J. D., & Talbot, B. 2013. ‘Smoking’ mephedrone: The identification of the pyrolysis products of 4-methylmethcathinone hydrochloride. Drug Testing and Analysis (5):291–305.
Kehr, J., Ichinose, F., Yoshitake, S., Goiny, M., Sievertsson, T. & Nyberg, F. 2011. Mephedrone, compared to MDMA (ecstasy) and amphetamine, rapidly increases both dopamine and serotonin levels in nucleus accumbens of awake rats. British Journal of Pharmacology, 164 (8): 1949-1958.
Kelly J. P. 2011. Cathinone derivatives: A review of their chemistry, pharmacology and toxicology. Drug Testing and Analysis (3): 439-435.
Levitas, M.P., Andrews, E., Lurie, I., Marginean, I., 2018. Discrimination of synthetic cathinones by GC-MS and GC-MS/MS using cold electron ionization. Forensic Sci. Int. (288): 107–114.
Linharta, I., Himla, M., Židková, M., Balíková, M., Lhotkovác, E., & Pálenícek, T. 2016. Metabolic profile of mephedrone: Identification of nor-mephedrone conjugates with dicarboxylic acids as a new type of xenobiotic phase II Metabolites. Toxicology Letters, (204): 54.62.
Lisek, R., Xu, W., Yuvasheva, E., Chiu, Y., Reitz, A., Liu-Chen, L. & Rawls, S. 2014. Mephedrone (‘bath salt’) elicits conditioned place preference and dopaminesensitive motor activation. Drug and Alcohol Dependence, (3): 257-262.
López-Rabuñala, Á., Lendoiro, E., Concheiro, M., López-Rivadulla, M., Cruz, A., & de-Castro-Ríos, A. (2019). A LC-MS/MS method for the determination of common synthetic cathinones in meconium. Journal of Chromatography B, (5): 349-355.
Martinez-Clemente, J., Escubedo E, Pubill. & Camarasa. 2012. nteraction of mephedrone with dopamine and serotonin targets in rats. European Neuropsychopharmacology 3 (22): 231-236.
Martınez-Clemente, J., Lopez-Arnau, R., Abad, S., Pubill, D., Escubedo, E., & Camarasa, J. 2014. Dose and Time-Dependent Selective Neurotoxicity Induced by Mephedrone in Mice. Plos One (50): 1-11.
Mercieca, G., Odoardi, S., Cassar, M., & Strano Rossi, S. (2018). Rapid and simple procedure for the determination of cathinones, amphetamine-like stimulants and other new psychoactive substances in blood and urine by GC–MS. Journal of Pharmaceutical and Biomedical Analysis, (149): 494-501.
Meyer, M. R., Wilhelm, J., Peters, F. T. & Maurer, H. H. 2013. Beta-keto amphetamines: studies on the metabolism of the designer drug mephedrone and toxicological detection of mephedrone, butylone, and methylone in urine using gas chromatography-mass spectrometry. Analytical and Bioanalytical Chemistry 3 (397): 1225-1233.
Meyer M. R & Maurer H. H. 2010. Metabolism of designer drugs of abuse: an updated review. Current Drug Metabolism 11 (5): 468-482.
Mori, T., Ito, S., Kita, T. & Sawaguchi, T. 2007. Effects of dopamine- and serotoninrelated compounds on methamphetamine-induced self-injurious behavior in mice. Journal of Pharmacological Sciences (96): 459–464.
Newman, J., He, W., & Verdin, E. 2012. Mitochondrial protein acylation and intermediary metabolism: regulation by sirtuins and implications for metabolic disease. Journal of Biological Chemistry (287): 42436–42443.
Pedersen, L., Johansen, S. S. & Linnet, K. 2015. In vitro metabolism studies on mephedrone and analysis of forensic cases. Drug Testing and Analysis, (1): 3-6.
Power M. 2010. How mephedrone shook the drug trade. Obtenido de http://www.drugscope.org.uk/Resources/Drugscope/Documents/PDF/Good%20Practice/DruglinkJanFeb10.pdf,
Power, J. D., Kavanagh, P., McLaughlin, G., O’Brien, J., Talbot, B., Barry, M. & Brandt, S. D. 2015. Identification and characterization of an imidazolium by-product formed during the synthesis of 4-methylmethcathinone (mephedrone). Drug Testing and Analysis (7): 894-902.
Power, P. McGlynn, K. Clarke, S.D. McDermott, P. Kavanagh & J. O'Brien (2011), The analysis of substituted cathinones. Part 1: chemical analysis of 2-, 3- and 4-methylmethcathinone, Forensic Sci Int 212(1-3): 6-12.
Pozo, O., Ibáñez, M., Sancho, J., Lahoz-Beneyetez, J. & Papaseit, M. 2015. Mass spectrometric evaluation of mephedrone in vivo human metabolism: identification of phase I and phase II metabolites including a novel succinyl conjugate. Drug Metabolism and Disposition (43): 248–257.
Razavipanah, I., Alipour, E., Deiminiat, B., & Hossein Rounaghi, G. 2018. A novel electrochemical imprinted sensor for ultrasensitive detection of the new psychoactive substance “Mephedrone”. Biosensors and Bioelectronics, (119): 163-169.
Schifano, F., Albanese, A., Fergus, S., Stair, J. L., Deluca, P., Corazza, O. & Ghods, H. 2011. Mephedrone (4-methylmethcathinone; ‘meow meow’): chemical, pharmacological and clinical issues. Psychopharmacology (214): 593-602.
Shortall, Spicer, C., Ebling, F., Green, A., Fone, K. & King, N. 2016. Contribution of serotonin and dopamine to changes in core body temperature and locomotor activity in rats following repeated administration of mephedrone. Addiction Biology (21): 1127–1139.
Simmler L. D 2013. Pharmacological characterization of designer cathinones in vitro. British Journal of Pharmacology (168): 458–470.
Sparago, M., Wlos J, Yuan J, Hatzidimitriou G, Tolliver J, & Dal Cason, T. A. 2001. Neurotoxic and pharmacologic studies on enantiomers of the N-methylated analog of cathinone (methcathinone): a new drug of abuse. Journal of Pharmacology and Experimental Therapeutics (279): 1043–1052.
Strano Rossi, S., Odoardi, S., Gregori, A., Peluso, G., Ripani, L., Ortar G., Serpelloni,G. & Romolo, F.S, 2014 An analytical approach to the forensic identification of different classes of new psychoactive substances (NPSs) in seized materials, Rapid Commun Mass Spectrom 28(17): 1904-1916.
Swortwood, M.J., Boland, D.M. & DeCaprio, A.P., 2013. Determination of 32 cathinone derivatives and other designer drugs in serum by comprehensive LC-Q-MS/MS analysis. Anal. Bioanal. Chem. 405 (4): 1383–1397.
Torrance, G. C. 2010. The detection of mephedrone (4-methylmethcathinone) in 4 fatalities in Scotland. Forensic Science International (13): 62-63.
Vardakou, I., Pistos, C., & Spiliopoulou, C. 2011. Drugs for youth via Internet and the example of mephedrone. Toxicology Letters (211): 191-195.
Winstock, A., Mitcheson, L., & Marsden, J. 2010. Mephedrone: still available and twice the price. The Lancet, (9752): 376-1537.
Winstock, A. R., Mitcheson, L. R., Deluca, P., Davey, Z., Corazza, O., & Schifano, F. 2010. Mephedrone, new kid for the chop? Addiction (106): 154–161.
Wood, D. M., Susannah, D., Puchnarewicz, M., Button, J., Archer, R., Ovaska, H. & Dargan, P. I. 2017. Recreational Use of Mephedrone (4-Methylmethcathinone, 4-MMC) with Associated Sympathomimetic Toxicity. Journal of Medical Toxicology (6): 327-330.
Zuba, D. & Adamowicz, P. 2016 Distinction of constitutional isomers of mephedrone by chromatographic and spectrometric methods, Aust J Forensic Sci 49(6): 1-13.
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2020-12-14
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Ángulo Florez, D. H., & Cipagauta Esquivel, E. C. (2020). Métodos de análise química para a detecção de 4-metilmetcatinona (mefedrina), desde uma perspectiva farmacológica e toxicológica. Cultura Científica, 1(18), 95–120. https://doi.org/10.38017/1657463X.686
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Artículo de Investigación Científica y Tecnológica
