4-Methylcathinone

Last updated
4-Methylcathinone
4-Methylcathinone.png
4-MethylCathinone.png
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
  • 2-amino-1-(4-methylphenyl)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C10H13NO
Molar mass 163.220 g·mol−1
3D model (JSmol)
  • CC1=CC=C(C=C1)C(=O)C(C)N
  • InChI=1S/C10H13NO/c1-7-3-5-9(6-4-7)10(12)8(2)11/h3-6,8H,11H2,1-2H3
  • Key:OHULHWHSUJEYIT-UHFFFAOYSA-N

4-Methylcathinone (also known as Nor-Mephedrone, 4-MC and NSC-60487), is a stimulant drug of the cathinone chemical class. It is a metabolite of the better known drug mephedrone (4-methylmethcathinone). [1] [2] [3] [4]

4-Methylcathinone displays a 2.4-fold selectivity to promote monoamine release via DAT over SERT as opposed to 309-fold selectivity for cathinone. [5] It also releases norepinephrine. [5]

See also

Related Research Articles

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Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

<span class="mw-page-title-main">Ethylone</span> Chemical compound

Ethylone, also known as 3,4-methylenedioxy-N-ethylcathinone, is a recreational designer drug classified as an entactogen, stimulant, and psychedelic of the phenethylamine, amphetamine, and cathinone chemical classes. It is the β-keto analogue of MDEA ("Eve"). Ethylone has only a short history of human use and is reported to be less potent than its relative methylone. In the United States, it began to be found in cathinone products in late 2011.

<span class="mw-page-title-main">Methedrone</span> Chemical compound of the cathinone class

Methedrone is a recreational drug of the cathinone chemical class. Chemically, methedrone is closely related to para-methoxymethamphetamine (PMMA), methylone and mephedrone. Methedrone received media attention in 2009 after the death of two young Swedish men. In both cases toxicology analysis showed methedrone was the only drug present in both men during the time of their overdose and subsequent deaths.

<span class="mw-page-title-main">Mephedrone</span> Synthetic stimulant drug

Mephedrone, also known as 4-methylmethcathinone, 4-MMC, and 4-methylephedrone, is a synthetic stimulant drug belonging to the amphetamine and cathinone classes. It is commonly referred to by slang names such as drone, M-CAT, White Magic, meow meow,and bubble. Chemically, it is similar to the cathinone compounds found in the Khat plant, native to eastern Africa.

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<span class="mw-page-title-main">4-Methylmethamphetamine</span> Stimulant and entactogen drug of the amphetamine class

4-Methylmethamphetamine (4-MMA), also known as mephedrine, is a putative stimulant and entactogen drug of the amphetamine family. It acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA). The drug is the β-deketo analogue of mephedrone and the N-methyl analogue of 4-methylamphetamine (4-MA).

<span class="mw-page-title-main">Naphyrone</span> Substituted cathinone stimulant drug

Naphyrone, also known as O-2482 and naphthylpyrovalerone, is a substituted cathinone drug derived from pyrovalerone that acts as a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI), producing stimulant effects and has been reported as a novel designer drug. No safety or toxicity data is available on the drug.

<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

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3-Fluoromethcathinone is a chemical compound of the phenethylamine, amphetamine, and cathinone classes that has been sold online as a designer drug. It is a structural isomer of flephedrone (4-fluoromethcathinone).

<span class="mw-page-title-main">4-Methylethcathinone</span> Stimulant designer drug

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<span class="mw-page-title-main">Bath salts (drug)</span> Recreational drug often superficially resembling true bath salts

Bath salts are a group of recreational designer drugs. The name derives from instances in which the drugs were disguised as bath salts. The white powder, granules, or crystals often resemble Epsom salts, but differ chemically. The drugs' packaging often states "not for human consumption" in an attempt to circumvent drug prohibition laws. Additionally, they may be described as "plant food", "powdered cleaner", or other products.

<i>N</i>-Ethylbuphedrone Stimulant of the cathinone class

N-Ethylbuphedrone is a stimulant of the cathinone class that has been sold as a designer drug. It is the β-ketone analogue of N,alpha-diethylphenylethylamine.

<span class="mw-page-title-main">3-Methylmethcathinone</span> Substituted cathinone designer drug

3-Methylmethcathinone (3-MMC), also known as metaphedrone, is a designer drug from the substituted cathinone family. 3-MMC is a monoamine transporter substrate that potently releases and inhibits the reuptake of dopamine and norepinephrine, as well as displaying moderate serotonin releasing activity.

<span class="mw-page-title-main">4-Methylbuphedrone</span> Designer stimulant drug

4-Methylbuphedrone, is a stimulant drug of the cathinone class that has been sold online as a designer drug.

<span class="mw-page-title-main">4-Chloromethcathinone</span> Simulant drug of the cathinone class

4-Chloromethcathinone is a stimulant drug of the cathinone class that has been sold online as a designer drug.

<span class="mw-page-title-main">Mexedrone</span> Stimulant and entactogen drug

Mexedrone is a stimulant and an entactogen drug of the cathinone class that has been sold online as a designer drug. It is the alpha-methoxy derivative of Mephedrone.

<span class="mw-page-title-main">3-Chloromethcathinone</span> Stimulant designer drug

3-Chloromethcathinone (3-CMC), also known as clophedrone, is a synthetic substance belonging to the cathinone class of psychoactive compounds. It is very similar in structure to other methcathinone derivatives such as 3-MMC and 4-CMC. Unlike cathinone, which occurs naturally in the khat plant Catha edulis, 3-CMC is not found in nature and is solely produced through chemical synthesis.

<span class="mw-page-title-main">2-Methylmethcathinone</span> Stimulant designer drug of the substituted cathinone class

2-Methylmethcathinone (2-MMC), also known as ortomephedrone is a recreational designer drug with stimulant and euphoric effects. It is a substituted cathinone derivative, closely related to better known drugs such as 3-methylmethcathinone and 4-methylmethcathinone (mephedrone). It was first identified in Sweden in 2014, and has subsequently been reported in other European countries such as Poland and Spain.

<span class="mw-page-title-main">2-Fluoromethcathinone</span> Designer stimulant

2-Fluoromethcathinone (2-FMC), also known as 2-flephedrone, is a psychostimulant and designer drug of the cathinone family. It acts as a dopamine and norepinephrine releasing agent (NDRA).

References

  1. "nor-Mephedrone". Cayman Chemical. Retrieved 27 June 2015.
  2. Meyer MR, Wilhelm J, Peters FT, Maurer HH (June 2010). "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. 397 (3): 1225–33. doi:10.1007/s00216-010-3636-5. PMID   20333362. S2CID   21471611.
  3. Pedersen AJ, Reitzel LA, Johansen SS, Linnet K (June 2013). "In vitro metabolism studies on mephedrone and analysis of forensic cases". Drug Testing and Analysis. 5 (6): 430–8. doi:10.1002/dta.1369. PMID   22573603.
  4. Dargan PI, Sedefov R, Gallegos A, Wood DM (July–August 2011). "The pharmacology and toxicology of the synthetic cathinone mephedrone (4-methylmethcathinone)". Drug Testing and Analysis. 3 (7–8): 454–63. doi:10.1002/dta.312. PMID   21755604.
  5. 1 2 Hutsell BA, Baumann MH, Partilla JS, Banks ML, Vekariya R, Glennon RA, Negus SS (February 2016). "Abuse-related neurochemical and behavioral effects of cathinone and 4-methylcathinone stereoisomers in rats". European Neuropsychopharmacology. 26 (2): 288–297. doi:10.1016/j.euroneuro.2015.12.010. PMC   5331761 . PMID   26738428.