1189805-46-6

Basic information

• Product Name: 2-(Methylamino)-1-(4-methylphenyl)-1-propanone
• Synonyms: 2-(Methylamino)-1-(4-methylphenyl)-1-propanone;1-Propanone,2-(MethylaMino)-1-(4-Methylphenyl)-;4-methyl ephedrone;Mephedrone,4-methyl methcathinone
• CAS NO: 1189805-46-6
• Molecular Formula: C11H15NO
• Molecular Weight: 177.2429
• Product Categories: pharmaceutical intermediate
• Mol File: 1189805-46-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 232℃
• Boiling Point: 280.2 °C at 760 mmHg
• Flash Point: 109.6 °C
• Appearance: /
• Density: 0.987 g/cm³
• PKA: 7.41±0.10(Predicted)
• CAS DataBase Reference: 2-(Methylamino)-1-(4-methylphenyl)-1-propanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Methylamino)-1-(4-methylphenyl)-1-propanone(1189805-46-6)
• EPA Substance Registry System: 2-(Methylamino)-1-(4-methylphenyl)-1-propanone(1189805-46-6)

Safety Data

• Hazardous Substances Data: 1189805-46-6(Hazardous Substances Data)

Usage

Description

Mephedrone hydrochloride salt is a white powder, whereas its free base is a yellowish liquid at ambient temperature. Mephedrone is typically sold as water-soluble crystalline stable hydrochloride salt powder, white or lightly colored; most probably as a racemic mixture of the R and S enantiomers. The powder can be dissolved for oral/rectal use or for injection. Mephedrone has also been found as capsules containing powder and as tablets pressed from powder.

Uses

Mephedrone is used in recreational settings because of its stimulant effects similar to amphetamines (particularlyMDMA) and cocaine. Mephedrone has no established or acknowledged medical value or use (human or veterinary). There are no indications that it may be used for any other purpose.

Definition

ChEBI: A propanone that is propiophenone substituted at C-4 and at C-beta with methyl and methylamino groups respectively. It is a synthetic stimulant and entactogen drug of the amphetamine and cathinone classes.

Toxicity evaluation

The effect profile and clinical presentations of mephedrone intoxications share some features seen with MDMA and cocaine (e.g., seizures, agitation, paranoia, hallucinations), implicitly supporting a sympathomimetic activity of mephedrone. Conversely, symptoms of depression and anhedonia could be tentatively associated to a putative depletion of serotonin and dopamine as a consequence of drug use, similarly to what may occur with other stimulants. In fact, binge administration of mephedrone (4 ×10 or 25 mg kg-1 sc per injection), in a rat model, results in a rapid decrease in striatal dopamine (DA) and hippocampal serotonin (5-hydroxytryptamine; 5-HT) transporter function. Like MDMA, but unlike methamphetamine or methcathinone, repeated mephedrone administrations also caused persistent serotonergic, but not dopaminergic, deficits.

Upstream product

• 1189726-22-4 (RS)-2-methylamino-1-(4-methylphenyl)propan-1-one hydrochloride 
• 108-88-3 toluene 
• 5337-93-9 4'-methylpropiophenone 
• 92821-88-0 2-bromo-4'-methylpropiophenone 
• 74-89-5 methylamine 

Downstream Products

• 1388142-32-2 4-methylmethcathinone 
• 1388142-31-1 R-mephedrone 
• 27465-54-9 2-(methylamino)-1-(p-tolyl)propan-1-ol 

Relevant articles and documents

X-ray structures and computational studies of several cathinones

2-(Ethylamino)-1-(4-methylphenyl)propan-1-one (shortly named 4-MEC) (1a), 1-(1,3-benzodioxol-5-yl)-2-(methylamino)propan-1-one (shortly named methylone or 3,4-methylenedioxymethcathinone) (1b), 1-(3,4-dimethylphenyl)-2-(methylamino) propan-1-one (1c), 2-m

Novel benzene-based carbamates for ache/bche inhibition: Synthesis and ligand/structure-oriented sar study

A series of new benzene-based derivatives was designed, synthesized and comprehensively characterized. All of the tested compounds were evaluated for their in vitro ability to potentially inhibit the acetyl-and butyrylcholinesterase enzymes. The selectivity index of individual molecules to cholinesterases was also determined. Generally, the inhibitory potency was stronger against butyryl-compared to acetylcholinesterase; however, some of the compounds showed a promising inhibition of both enzymes. In fact, two compounds (23, benzyl ethyl(1-oxo-1-phenylpropan-2-yl)carbamate and 28, benzyl (1-(3-chlorophenyl)-1-oxopropan-2-yl) (methyl)carbamate) had a very high selectivity index, while the second one (28) reached the lowest inhibitory concentration IC50 value, which corresponds quite well with galanthamine. Moreover, comparative receptor-independent and receptor-dependent structure–activity studies were conducted to explain the observed variations in inhibiting the potential of the investigated carbamate series. The principal objective of the ligand-based study was to comparatively analyze the molecular surface to gain insight into the electronic and/or steric factors that govern the ability to inhibit enzyme activities. The spatial distribution of potentially important steric and electrostatic factors was determined using the probability-guided pharmacophore mapping procedure, which is based on the iterative variable elimination method. Additionally, planar and spatial maps of the host–target interactions were created for all of the active compounds and compared with the drug molecules using the docking methodology.