3,4-Dimethylmethcathinone

Last updated
3,4-Dimethylmethcathinone
3,4-DMMC.svg
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • (±)-1-(3,4-Dimethylphenyl)-2-(methylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H17NO
Molar mass 191.274 g·mol−1
3D model (JSmol)
  • Cc1ccc(C(=O)C(C)NC)cc1C
  • InChI=1S/C12H17NO/c1-8-5-6-11(7-9(8)2)12(14)10(3)13-4/h5-7,10,13H,1-4H3 Yes check.svgY
  • Key:IBZRXTVDTGVBIS-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

3,4-Dimethylmethcathinone (3,4-DMMC) is a stimulant drug first reported in 2010 as a designer drug analogue of mephedrone, apparently produced in response to the banning of mephedrone, following its widespread abuse in many countries in Europe and around the world. [1] 3,4-DMMC has been seized as a designer drug in Australia. [2] In vitro, 3,4-DMMC was shown to be a monoamine transporter substrate that potently inhibits norepinephrine and serotonin reuptake, and to a lesser extent dopamine reuptake. [3]

Contents

As of October 2015 3,4-DMMC is a controlled substance in China. [4]

3,4-DMMC is banned in the Czech Republic. [5]

In the United States 3,4-DMMC is considered a Schedule I controlled substance as a positional isomer of 4-Methylethcathinone (4-MEC). [6]

See also

Related Research Articles

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

3-Trifluoromethylphenylpiperazine (TFMPP) is a recreational drug of the phenylpiperazine chemical class and is a substituted piperazine. Usually in combination with benzylpiperazine (BZP) and other analogues, it is sold as an alternative to the illicit drug MDMA ("Ecstasy").

<span class="mw-page-title-main">Butylone</span> Entactogen, psychedelic, and stimulant drug of the phenethylamine class

Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine, amphetamine, phenylisobutylamine, and cathinone families. It is the β-keto analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.

<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

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">4-Fluoroamphetamine</span> Psychoactive research chemical

4-Fluoroamphetamine, also known as para-fluoroamphetamine (PFA) is a psychoactive research chemical of the phenethylamine and substituted amphetamine chemical classes. It produces stimulant and entactogenic effects. As a recreational drug, 4-FA is sometimes sold along with related compounds such as 2-fluoroamphetamine and 4-fluoromethamphetamine.

<span class="mw-page-title-main">Ethylphenidate</span> Stimulant analog of methylphenidate

Ethylphenidate (EPH) is a central nervous system (CNS) stimulant and a close analog of methylphenidate.

<span class="mw-page-title-main">4-Bromomethcathinone</span> Psychoactive drug and research chemical

4-Bromomethcathinone is a psychoactive drug and research chemical of the phenethylamine, amphetamine, and cathinone chemical classes. It acts as a serotonin and norepinephrine reuptake inhibitor, but acts more like an antidepressant than a stimulant. Halogenated cathinones, including 4-BMC, possess neurotoxic and cytotoxic properties.

<span class="mw-page-title-main">5-APDB</span> Chemical compound

5-(2-Aminopropyl)-2,3-dihydrobenzofuran is a putative entactogen drug of the phenethylamine and amphetamine classes. It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge. 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead. 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic analogues of MDMA.

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

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects.

α-Pyrrolidinopentiophenone Chemical compound

α-Pyrrolidinopentiophenone (α-PVP), also known as α-pyrrolidinovalerophenone, O-2387, β-keto-prolintane, prolintanone, or desmethylpyrovalerone, is a synthetic stimulant of the cathinone class developed in the 1960s that has been sold as a designer drug and often consumed for recreational reasons. α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.

<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">3-Fluoroamphetamine</span> Stimulant drug that acts as an amphetamine

3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.

<span class="mw-page-title-main">3,4-Dichloromethylphenidate</span> Stimulant drug

3,4-dichloromethylphenidate is a potent stimulant drug from the phenidate class closely related to methylphenidate. It acts as a potent serotonin-norepinephrine-dopamine reuptake inhibitor with a long duration of action. It has been sold online as a designer drug.

<span class="mw-page-title-main">Methiopropamine</span> Structural analog of methamphetamine

Methiopropamine (MPA), also known as N-methylthiopropamine, is an organic compound structurally related to methamphetamine. Originally reported in 1942, the molecule consists of a thiophene group with an alkyl amine substituent at the 2-position. It appeared for public sale in the United Kingdom in December 2010 as a "research chemical" or "legal high", recently branded as Blow. It has limited popularity as a recreational stimulant.

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

Pentedrone is a stimulant of the cathinone class that has been sold as a designer drug and has been found since 2010 as an ingredient in a number of "bath salt" mixes sold as legal highs.

A monoamine reuptake inhibitor (MRI) is a drug that acts as a reuptake inhibitor of one or more of the three major monoamine neurotransmitters serotonin, norepinephrine, and dopamine by blocking the action of one or more of the respective monoamine transporters (MATs), which include the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT). This in turn results in an increase in the synaptic concentrations of one or more of these neurotransmitters and therefore an increase in monoaminergic neurotransmission.

<span class="mw-page-title-main">5-MAPB</span> Chemical compound

5-MAPB, also known as 5-(N-methyl-2-aminopropyl)benzofuran, is an entactogen and designer drug of the amphetamine family that is similar to MDMA in its structure and effects.

<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-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.

References

  1. "EMCDDA Annual Report 2010" (PDF). Archived from the original (PDF) on 2012-03-14. Retrieved 2011-10-03.
  2. Locos O, Reynolds D (September 2012). "The characterization of 3,4-dimethylmethcathinone (3,4-DMMC)". Journal of Forensic Sciences. 57 (5): 1303–6. doi:10.1111/j.1556-4029.2012.02142.x. PMID   22564211. S2CID   205770717.
  3. Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME (2018). "Pharmacological profile of mephedrone analogs and related new psychoactive substances" (PDF). Neuropharmacology. 15 (134): 4–12. doi:10.1016/j.neuropharm.2017.07.026. PMID   28755886. S2CID   28786127.
  4. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  5. "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví. Archived from the original (PDF) on 2016-03-09. Retrieved 2016-02-06.
  6. "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). U.S. Department of Justice. February 2023. Retrieved 2023-03-05.