1189726-22-4

Basic information

• Product Name: 2-(Methylamino)-1-(4-methylphenyl)-1-propanone hydrochloride
• Synonyms: 2-(Methylamino)-1-(4-methylphenyl)-1-propanone hydrochloride;Methanol(Mephedrone HCl, 1.0 mg/mL (as free base);Mephedrone HCl;4-Methylmethcathinone (hydrochloride);2-(MethylaMino)-1-(p-tolyl)propan-1-one hydrochloride;Mephedrone 2-MethylaMino-1-p-tolylpropan-1-one;Mephedrone Hydrochloride (1.0 Mg/ML in Methanol);Mephedrone hydrochloride solution
• CAS NO: 1189726-22-4
• Molecular Formula: C11H15NO.HCl
• Molecular Weight: 213.70384
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;pharmaceutical intermediate
• Mol File: 1189726-22-4.mol

Chemical Properties

• Melting Point: 239-241?C (dec.)
• Flash Point: 9℃
• Appearance: white to off-white/
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: DMSO: >20mg/mL
• CAS DataBase Reference: 2-(Methylamino)-1-(4-methylphenyl)-1-propanone hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Methylamino)-1-(4-methylphenyl)-1-propanone hydrochloride(1189726-22-4)
• EPA Substance Registry System: 2-(Methylamino)-1-(4-methylphenyl)-1-propanone hydrochloride(1189726-22-4)

Safety Data

• Hazard Codes: T,F
• Statements: 25-43-39/23/24/25-23/24/25-11
• Safety Statements: 36/37-45-16
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• Hazardous Substances Data: 1189726-22-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-(Methylamino)-1-(4-methylphenyl)-1-propanone hydrochloride is used as a research chemical for studying the effects and mechanisms of action of stimulant drugs. Its structural similarity to cathinone and methcathinone makes it a valuable tool for understanding the pharmacological properties of these compounds and their potential therapeutic applications.
Used in Recreational Drug Market:
In the recreational drug market, 2-(Methylamino)-1-(4-methylphenyl)-1-propanone hydrochloride is used as a stimulant for its psychoactive effects. It is often sought after for its ability to produce euphoria, increased energy, and heightened sociability, similar to the effects of MDMA and methylone.
Used in Toxicological Analysis:
2-(Methylamino)-1-(4-methylphenyl)-1-propanone hydrochloride is also used in toxicological analysis to detect and identify the presence of this substance in biological samples. This is important for forensic investigations and understanding the prevalence and impact of its use in various populations.
Used in Drug Policy and Regulation:
The study of 2-(Methylamino)-1-(4-methylphenyl)-1-propanone hydrochloride also contributes to drug policy and regulation efforts, as understanding its effects and prevalence can inform the development of strategies to control its distribution and use, as well as to mitigate its potential harms.

Biochem/physiol Actions

Mephedrone is an inhibitor of monoamine transporter present in the brain and periphery. Mephedrone bears a chiral center and can be found in two enantiomers R-mephedrone and S-mephedrone. Its racemic form is often used as a drug. Mephedrone in rats is known to cause high blood pressure and heart rate, as well as stimulates locomotor hyperactivity. Human trail reveal that mephedrone has the ability to induce euphoria and pleasure.

Upstream product

• 92821-88-0 2-bromo-4'-methylpropiophenone 
• 74-89-5 methylamine 
• 5337-93-9 4'-methylpropiophenone 
• 69673-92-3 α-chloro-4-methyl propiophenone 
• 108-88-3 toluene 

Relevant articles and documents

Stereochemistry of mephedrone neuropharmacology: Enantiomer-specific behavioural and neurochemical effects in rats

BACKGROUND AND PURPOSE: Synthetic cathinones, commonly referred to as 'bath salts', are a group of amphetamine-like drugs gaining popularity worldwide. 4-Methylmethcathinone (mephedrone, MEPH) is the most commonly abused synthetic cathinone in the UK, and exerts its effects by acting as a substrate-type releaser at monoamine transporters. Similar to other cathinone-related compounds, MEPH has a chiral centre and exists stably as two enantiomers: R-mephedrone (R-MEPH) and S-mephedrone (S-MEPH). EXPERIMENTAL APPROACH: Here, we provide the first investigation into the neurochemical and behavioural effects of R-MEPH and S-MEPH. We analysed both enantiomers in rat brain synaptosome neurotransmitter release assays and also investigated their effects on locomotor activity (e.g. ambulatory activity and repetitive movements), behavioural sensitization and reward. KEY RESULTS: Both enantiomers displayed similar potency as substrates (i.e. releasers) at dopamine transporters, but R-MEPH was much less potent than S-MEPH as a substrate at 5-HT transporters. Locomotor activity was evaluated in acute and repeated administration paradigms, with R-MEPH producing greater repetitive movements than S-MEPH across multiple doses. After repeated drug exposure, only R-MEPH produced sensitization of repetitive movements. R-MEPH produced a conditioned place preference whereas S-MEPH did not. Lastly, R-MEPH and S-MEPH produced biphasic profiles in an assay of intracranial self-stimulation (ICSS), but R-MEPH produced greater ICSS facilitation than S-MEPH. CONCLUSIONS AND IMPLICATIONS: Our data are the first to demonstrate stereospecific effects of MEPH enantiomers and suggest that the predominant dopaminergic actions of R-MEPH (i.e. the lack of serotonergic actions) render this stereoisomer more stimulant-like when compared with S-MEPH. This hypothesis warrants further study.

Is the 3,4-methylendioxypyrovalerone/mephedrone combination responsible for enhanced stimulant effects? A rat study with investigation of the effect/concentration relationships

Rationale: The use of synthetic cathinones as recreational drugs frequently sold in combination has been increasing exponentially. However, the consequences of combining cathinones on the resulting stimulant effects and the pharmacokinetics have been poorly investigated. Objective and methods: To study 3,4-methylenedioxypyrovalerone (MDPV; 3?mg/kg) and mephedrone (4-MMC; 30?mg/kg)-induced effects on rat locomotor activity and pharmacokinetics, administered alone or in combination by the intragastric route. The pharmacokinetic parameters were determined using non-compartmental analysis and the relationships between the locomotor activity and drug concentrations using sigmoidal Emax modeling. Results: Locomotor activity significantly increased during the first hour post-administration with the MDPV/4-MMC combination in comparison to MDPV (p max (16.4 ± 5.5 versus 62.2 ± 14.2?μg/L, p 0 → ∞ (708 ± 91 versus 3316 ± 682?μg/L/min, p max model fitted the observed data well; MDPV being markedly more potent than 4-MMC (EC50, 0.043 versus 0.7?μmol/L). The enhancing factor representing the MDPV contribution to the alteration in the relationships between locomotor activity and 4-MMC concentrations was 0.3. Conclusion: An MDPV/4-MMC combination results in enhanced stimulant effects in the rat, despite significant reduction in MDPV bioavailability. Enhanced effects could be explained by increased MDPV distribution and/or possible complementation at the brain dopaminergic targets. However, the exact consequences of the MDPV/4-MMC combination in humans remain to be clarified.

Phase I metabolites of mephedrone display biological activity as substrates at monoamine transporters

Background and Purpose: 4-Methyl-N-methylcathinone (mephedrone) is a synthetic stimulant that acts as a substrate-type releaser at transporters for dopamine (DAT), noradrenaline (NET) and 5-HT (SERT). Upon systemic administration, mephedrone is metabolized to several phase I compounds: the N-demethylated metabolite, 4-methylcathinone (nor-mephedrone); the ring-hydroxylated metabolite, 4-hydroxytolylmephedrone (4-OH-mephedrone); and the reduced keto-metabolite, dihydromephedrone. Experimental Approach: We used in vitro assays to compare the effects of mephedrone and synthetically prepared metabolites on transporter-mediated uptake and release in HEK293 cells expressing human monoamine transporters and in rat brain synaptosomes. In vivo microdialysis was employed to examine the effects of i.v. metabolite injection (1 and 3?mg·kg?1) on extracellular dopamine and 5-HT levels in rat nucleus accumbens. Key Results: In cells expressing transporters, mephedrone and its metabolites inhibited uptake, although dihydromephedrone was weak overall. In cells and synaptosomes, nor-mephedrone and 4-OH-mephedrone served as transportable substrates, inducing release via monoamine transporters. When administered to rats, mephedrone and nor-mephedrone produced elevations in extracellular dopamine and 5-HT, whereas 4-OH-mephedrone did not. Mephedrone and nor-mephedrone, but not 4-OH-mephedrone, induced locomotor activity. Conclusions and Implications: Our results demonstrate that phase I metabolites of mephedrone are transporter substrates (i.e. releasers) at DAT, NET and SERT, but dihydromephedrone is weak in this regard. When administered in vivo, nor-mephedrone increases extracellular dopamine and 5-HT in the brain whereas 4-OH-mephedrone does not, suggesting the latter metabolite does not penetrate the blood–brain barrier. Future studies should examine the pharmacokinetics of nor-mephedrone to determine its possible contribution to the in vivo effects produced by mephedrone.