Page last updated: 2024-11-13

methylone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Cross-References

ID SourceID
PubMed CID45789647
CHEMBL ID3604010
CHEBI ID182618
SCHEMBL ID1826389
MeSH IDM0352523

Synonyms (30)

Synonym
1-(1,3-benzodioxol-5-yl)-2-(methylamino)propan-1-one
CHEBI:182618
186028-79-5
methylone
3,4-methylenedioxy-n-methylcathinonmethylone
beta-keto-3,4-methylenedioxymethamphetamine
2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one
2-(methylamino)-1-(1,3-benzodioxol-5-yl)-1-propanone
C20126
dea no. 7540
3,4-methylenedioxy-n-methylcathinone
unii-l4i4b1r01f
1-propanone, 1-(1,3-benzodioxol-5-yl)-2-(methylamino)-
l4i4b1r01f ,
hsdb 7997
bk-mdma
methylenedioxymethcathinone
m1 (psychedelic)
j899.632f ,
mdmc
.beta.k-mdma
VKEQBMCRQDSRET-UHFFFAOYSA-N
SCHEMBL1826389
CHEMBL3604010 ,
J-510033
bdbm50114073
(rs)-methylone
Q4046265
DTXSID80870167
1-(2h-1,3-benzodioxol-5-yl)-2-(methylamino)propan-1-one

Research Excerpts

Overview

Methylone is a synthetic derivative of cathinone. It has emerged as a designer drug of abuse in Europe and the USA.

ExcerptReferenceRelevance
"Methylone is a cathinone derivative that has recently emerged as a designer drug of abuse in Europe and the USA. "( Serotonergic impairment and memory deficits in adolescent rats after binge exposure of methylone.
Camarasa, J; Escubedo, E; López-Arnau, R; Martínez-Clemente, J; Pubill, D, 2014
)
2.07
"Methylone is a synthetic derivative of cathinone. "( Death following ingestion of methylone.
Barrios, L; Boels, D; Bouquie, R; Clement, R; Grison-Hernando, H; Monteil-Ganiere, C, 2016
)
2.17

Effects

ExcerptReferenceRelevance
"Methylone has been assumed to induce hyperthermic effects through inhibition of serotonin and/or dopamine transporters (SERT and DAT, respectively)."( Methylone-induced hyperthermia and lethal toxicity: role of the dopamine and serotonin transporters.
Goda, Y; Hall, FS; Ito, M; Kikura-Hanajiri, R; Lesch, KP; Moriya, Y; Murphy, DL; Ohara, A; Piao, YS; Sora, I; Uhl, GR, 2015
)
2.58

Treatment

ExcerptReferenceRelevance
"Methylone-treated animals only displayed impairments in the probe trial of the Morris water maze, which concerns reference memory, while the spatial learning process seemed to be preserved."( Serotonergic impairment and memory deficits in adolescent rats after binge exposure of methylone.
Camarasa, J; Escubedo, E; López-Arnau, R; Martínez-Clemente, J; Pubill, D, 2014
)
1.35

Toxicity

Methylone has strong cytotoxic potential for the NPS 5F-PB-22 and MDAI. Moderate effects for MDMA, MDPV, methylone, cathinone, 4-MEC, and mephedrone. No toxic effects for methamphetamine.

ExcerptReferenceRelevance
" To examine the roles of each of these proteins in methylone-induced toxic effects, we used SERT and DAT knockout (KO) mice and assessed the hyperthermic and lethal effects caused by a single administration of methylone."( Methylone-induced hyperthermia and lethal toxicity: role of the dopamine and serotonin transporters.
Goda, Y; Hall, FS; Ito, M; Kikura-Hanajiri, R; Lesch, KP; Moriya, Y; Murphy, DL; Ohara, A; Piao, YS; Sora, I; Uhl, GR, 2015
)
2.11
" The present study showed strong cytotoxic potential for the NPS 5F-PB-22 and MDAI, moderate effects for MDMA, MDPV, methylone, cathinone, 4-MEC, and mephedrone, and no toxic effects for methamphetamine."( Cytotoxicity of new psychoactive substances and other drugs of abuse studied in human HepG2 cells using an adopted high content screening assay.
Beck, A; Flockerzi, V; Maurer, HH; Meyer, MR; Richter, LHJ, 2019
)
0.72

Pharmacokinetics

ExcerptReferenceRelevance
"Pharmacokinetic and pharmacodynamic analysis of methylone showed a correlation between plasma concentrations and enhancement of the locomotor activity."( An integrated pharmacokinetic and pharmacodynamic study of a new drug of abuse, methylone, a synthetic cathinone sold as "bath salts".
Camarasa, J; Carbó, Ml; Escubedo, E; López-Arnau, R; Martínez-Clemente, J; Pubill, D, 2013
)
0.87
" As such, the purpose of this study was to examine the pharmacokinetic profile of the 'bath salts' in a pregnancy model."( The pharmacokinetic profile of synthetic cathinones in a pregnancy model.
Brown, SD; Keasling, R; Kochelek, K; Pond, BB; Strange, LG, 2017
)
0.46
" The pharmacokinetic profiles of the synthetic cathinones vary based on the substitutions to the core scaffold."( A review of the influence of functional group modifications to the core scaffold of synthetic cathinones on drug pharmacokinetics.
Calinski, DM; Kisor, DF; Sprague, JE, 2019
)
0.51
"To provide a summary of the literature regarding the pharmacokinetic characteristics of the synthetic cathinones, with a focus on the impact of the structural modifications to the pharmacokinetics."( A review of the influence of functional group modifications to the core scaffold of synthetic cathinones on drug pharmacokinetics.
Calinski, DM; Kisor, DF; Sprague, JE, 2019
)
0.51
"In many, but not all, instances the pharmacokinetic characteristics of the synthetic cathinones can be reasonably predicted based on the substitutions to the core scaffold."( A review of the influence of functional group modifications to the core scaffold of synthetic cathinones on drug pharmacokinetics.
Calinski, DM; Kisor, DF; Sprague, JE, 2019
)
0.51
"Continued research will lead to a better understanding of the pharmacokinetic changes associated with structural modifications to the cathinone scaffold, and potentially in the long range, enhanced overdose and addiction therapy."( A review of the influence of functional group modifications to the core scaffold of synthetic cathinones on drug pharmacokinetics.
Calinski, DM; Kisor, DF; Sprague, JE, 2019
)
0.51
" In this study, we examine the pharmacokinetic interactions of the drug combination."( Pharmacokinetics of Synthetic Cathinones Found in Bath Salts in Mouse Brain and Plasma Using High-Pressure Liquid Chromatography-Tandem Mass Spectrometry.
Bouldin, JB; Brown, SD; Gearlds, C; McKinney, M; Pond, BB; Schreiner, S, 2021
)
0.62

Bioavailability

ExcerptReferenceRelevance
" Absolute bioavailability was about 80% and the percentage of methylone protein binding was of 30%."( An integrated pharmacokinetic and pharmacodynamic study of a new drug of abuse, methylone, a synthetic cathinone sold as "bath salts".
Camarasa, J; Carbó, Ml; Escubedo, E; López-Arnau, R; Martínez-Clemente, J; Pubill, D, 2013
)
0.86

Dosage Studied

Methylone and its three metabolites in rats were further investigated after a single intraperitoneal dosing of 5 mg kg-1 methylone hydrochloride. MDPV, αPVP, MCAT, and methylone) with a range of pharmacological effects were compared to cocaine and MDMA.

ExcerptRelevanceReference
" The time-course excretion profiles of methylone and its three metabolites in rats were further investigated after a single intraperitoneal dosing of 5 mg kg-1 methylone hydrochloride."( Metabolism of the recently encountered designer drug, methylone, in humans and rats.
Kamata, HT; Kamata, T; Katagi, M; Miki, A; Nishikawa, M; Shima, N; Tsuchihashi, H; Zaitsu, K, 2006
)
0.85
" The secondary aims were to investigate a possible dose-response CPP and whether the synthetic cathinones induce higher CPP than amphetamine at equal dose."( Mephedrone, methylone and 3,4-methylenedioxypyrovalerone (MDPV) induce conditioned place preference in mice.
Andersson, M; Karlsson, L; Kronstrand, R; Kugelberg, FC, 2014
)
0.78
" The dosage of δ9-tetrahydrocannabinol (THC) suggests a recent cannabis consumption (THC 12."( Death following ingestion of methylone.
Barrios, L; Boels, D; Bouquie, R; Clement, R; Grison-Hernando, H; Monteil-Ganiere, C, 2016
)
0.73
" Three new phase II metabolites, amidic conjugates of MDC with succinic, glutaric and adipic acid, were identified in the urine of rats dosed subcutaneously with MDMC."( Identification of three new phase II metabolites of a designer drug methylone formed in rats by N-demethylation followed by conjugation with dicarboxylic acids.
Balíková, M; Dvořáčková, V; Himl, M; Lhotková, E; Linhart, I; Páleníček, T; Židková, M, 2018
)
0.72
"32 mg/kg/inf) under a fixed ratio (FR) 1 schedule of reinforcement; and (2) full dose-response curves for each drug to maintain responding under an FR5 schedule of reinforcement."( Relative reinforcing effects of second-generation synthetic cathinones: Acquisition of self-administration and fixed ratio dose-response curves in rats.
Collins, GT; Galindo, KI; Gannon, BM; Mesmin, MP; Rice, KC; Sulima, A, 2018
)
0.48
"32 mg/kg/inf) under a fixed ratio (FR) 1 schedule of reinforcement and generated full dose-response curves for methylone (0."( Behavioral economic analysis of the reinforcing effects of "bath salts" mixtures: studies with MDPV, methylone, and caffeine in male Sprague-Dawley rats.
Collins, GT; Gannon, BM; Mesmin, MP; Rice, KC; Sulima, A, 2019
)
0.94
", MDPV, αPVP, MCAT, and methylone) with a range of pharmacological effects at dopamine and serotonin transporters were compared to cocaine and MDMA using dose-response analysis under a simple FR schedule and behavioral economic procedures that generated demand curves for two doses of each drug."( Reinforcing effects of synthetic cathinones in rhesus monkeys: Dose-response and behavioral economic analyses.
Bergman, J; de Moura, FB; Kohut, SJ; Paronis, CA; Prisinzano, TE; Sherwood, A, 2021
)
0.93
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzodioxoles
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1240849Binding affinity to NET in Sprague-Dawley rat brain synaptosomes assessed as induction of [3H]MPP+ release by liquid scintillation counting method2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID1240847Binding affinity to SERT in Sprague-Dawley rat brain synaptosomes assessed as induction of [3H]5-HT release by liquid scintillation counting method2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID1240848Binding affinity to DAT in Sprague-Dawley rat brain synaptosomes assessed as induction of [3H]MPP+ release by liquid scintillation counting method2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (101)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (0.99)18.2507
2000's6 (5.94)29.6817
2010's80 (79.21)24.3611
2020's14 (13.86)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews8 (7.48%)6.00%
Case Studies14 (13.08%)4.05%
Observational1 (0.93%)0.25%
Other84 (78.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]