2-Methylmethcathinone

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2-methylmethcathinone
2-MMC structure.png
Legal status
Legal status
Identifiers
  • 1-(2-methylphenyl)-2-(methylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C11H15NO
Molar mass 177.247 g·mol−1
3D model (JSmol)
  • CC1=CC=CC=C1C(=O)C(C)NC
  • InChI=1S/C11H15NO/c1-8-6-4-5-7-10(8)11(13)9(2)12-3/h4-7,9,12H,1-3H3
  • Key:PRGXFAWAMOFULD-UHFFFAOYSA-N

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). [1] [2] It was first identified in Sweden in 2014, [3] and has subsequently been reported in other European countries such as Poland [4] and Spain. [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">Methylenedioxypyrovalerone</span> Chemical compound

Methylenedioxypyrovalerone (MDPV) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI). It was first developed in the 1960s by a team at Boehringer Ingelheim. Its activity at the dopamine transporter is six times stronger than at the norepinephrine transporter and it is virtually inactive at the serotonin transporter. MDPV remained an obscure stimulant until around 2004 when it was reportedly sold as a designer drug. In the US, products containing MDPV and labeled as bath salts were sold as recreational drugs in gas stations, similar to the marketing for Spice and K2 as incense, until it was banned in 2011.

<i>alpha</i>-Pyrrolidinopropiophenone Chemical compound

α-Pyrrolidinopropiophenone (α-PPP), is a stimulant drug. It is similar in structure to the appetite suppressant diethylpropion and has analogous effects in animals. Little is known about this compound, but it has been detected by laboratories in Germany as an ingredient in "ecstasy" tablets seized by law enforcement authorities. This drug has been found to produce stimulant effects in animals and presumably also produces these effects in humans, based on the context in which it has been found.

<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">Phthalimidopropiophenone</span> Chemical compound

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<span class="mw-page-title-main">4'-Methyl-α-pyrrolidinopropiophenone</span> Chemical compound

4'-Methyl-α-pyrrolidinopropiophenone is a stimulant drug and substituted cathinone. It is structurally very similar to α-PPP, with only one added methyl group in the para position on the phenyl ring. 4-MePPP was sold in Germany as a designer drug in the late 1990s and early 2000s, along with a number of other pyrrolidinophenone derivatives. Although it has never achieved the same international popularity as its better-known relations α-PPP and MDPV, 4-MePPP is still sometimes found as an ingredient of grey-market "bath salt" blends such as "NRG-3".

<span class="mw-page-title-main">3',4'-Methylenedioxy-α-pyrrolidinobutiophenone</span> Stimulant drug

3',4'-Methylenedioxy-α-pyrrolidinobutyrophenone (MDPBP) is a stimulant of the cathinone class developed in the 1960s, which has been reported as a novel designer drug. MDPBP is sometimes sold under the name "NRG-1" as a mixture with other cathinone derivatives, including flephedrone, pentylone, MαPPP and its higher homologue MDPV. As with other cathinones, MDPBP has been shown to have reinforcing effects in rats.

<i>alpha</i>-Pyrrolidinopentiophenone Chemical compound

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

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<span class="mw-page-title-main">3-Fluoromethcathinone</span> Designer stimulant drug

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

4-Methylethcathinone or 4-MEC is a chemical that bears a chemical resemblance to mephedrone. Due to its similarity to mephedrone, it is thought to be a stimulant and entactogen drug of the phenethylamine, amphetamine, and cathinone chemical classes. It has been marketed alone or in mixtures with other substituted cathinones under the name "NRG-2", although other blends such as "NRG-1" may have been more ambiguous with their ingredients.

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 mislabeled as plant food, powdered cleaner, and other such products.

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

3-Methylmethcathinone, also known as 3-MMC and metaphedrone, is a designer drug from the substituted cathinone family. 3-MMC is closely related in structure to the more commonly known illicit drug mephedrone (4-MMC), and is also illegal in most countries that have banned mephedrone due to 3-MMC being a structural isomer of 4-MMC. However, 3-MMC has still appeared on the recreational drug market as an alternative to mephedrone, and was first identified being sold in Sweden in 2012. Unlike some synthetic cathinones, 3-MMC has been evaluated in at least one large mammal study. 3-MMC is a monoamine transporter substrate that potently inhibits norepinephrine uptake and displays more pronounced dopaminergic vs. serotonergic activity.

<i>alpha</i>-Pyrrolidinohexiophenone Stimulant drug

α-Pyrrolidinohexiophenone is a synthetic stimulant drug of the cathinone class developed in the 1960s which has been reported as a novel designer drug.

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

4-Methylcathinone, is a stimulant drug of the cathinone chemical class. It is a metabolite of the better known drug mephedrone (4-methylmethcathinone).

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

4-Methylpentedrone, is a stimulant drug of the cathinone class that has been sold online as a designer drug. It is a higher homolog of 4-methylmethcathinone (mephedrone) and 4-methylbuphedrone (4-MeMABP), and the p-methyl derivative of pentedrone. It can also be viewed as the methylamino analog of pyrovalerone.

<i>alpha</i>-Pyrrolidinopentiothiophenone Stimulant drug

α-Pyrro​lidino​pentio​thiophenone is a synthetic stimulant of the cathinone class that has been sold online as a designer drug. It is an analogue of α-PVP where the phenyl ring has been replaced by thiophene.

<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">TH-PVP</span> Chemical compound

TH-PVP is a substituted cathinone derivative which has been sold as a designer drug. It was first identified by a forensic laboratory in Hungary in 2015, but has subsequently been found in numerous other countries around the world including Spain, Belgium, Poland, Turkey and Brazil. Pharmacological studies in vitro showed it to inhibit reuptake and promote the release of monoamine neurotransmitters with some selectivity for serotonin, but it failed to produce stimulant effects in animals, and has a pharmacological profile more comparable to that of sedating empathogens such as MDAI and 5-Methyl-MDA.

References

  1. Maas A, Sydow K, Madea B, Hess C (April 2017). "Separation of ortho, meta and para isomers of methylmethcathinone (MMC) and methylethcathinone (MEC) using LC-ESI-MS/MS: Application to forensic serum samples". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 1051: 118–125. doi:10.1016/j.jchromb.2017.01.046. PMID   28262446.
  2. Nowak PM, Woźniakiewicz M, Mitoraj M, Sagan F, Kościelniak P (March 2018). "Thermodynamics of acid-base dissociation of several cathinones and 1-phenylethylamine, studied by an accurate capillary electrophoresis method free from the Joule heating impact". Journal of Chromatography A. 1539: 78–86. doi:10.1016/j.chroma.2018.01.047. PMID   29409596.
  3. "Europol 2014 Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). European Monitoring Centre for Drugs and Drug Addiction. 10 May 2005.
  4. Adamowicz P, Gieroń J, Gil D, Lechowicz W, Skulska A, Tokarczyk B (January 2016). "The prevalence of new psychoactive substances in biological material - a three-year review of casework in Poland". Drug Testing and Analysis. 8 (1): 63–70. doi:10.1002/dta.1924. PMID   26666629.
  5. Hart CL (2021). Drug use for grown-ups : chasing liberty in the land of fear. New York. ISBN   978-1-101-98164-1.{{cite book}}: CS1 maint: location missing publisher (link)