4,4'-Dimethylaminorex

Last updated
4,4'-Dimethylaminorex
4,4'-Dimethylaminorex.svg
Clinical data
Other names4,4'-DMAR
ATC code
  • none
Legal status
Legal status
  • BR: Class F2 (Prohibited psychotropics) [1]
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class A
  • US:Schedule I [2]
  • Illegal in Czech Republic and Sweden
Identifiers
  • 4-Methyl-5-(4-methylphenyl)-4,5-dihydro-1,3-oxazol-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C11H14N2O
Molar mass 190.246 g·mol−1
3D model (JSmol)
  • CC(N=C(N)O1)C1C2=CC=C(C)C=C2
  • InChI=1S/C11H14N2O/c1-7-3-5-9(6-4-7)10-8(2)13-11(12)14-10/h3-6,8,10H,1-2H3,(H2,12,13)
  • Key:NPILLHMQNMXXTL-UHFFFAOYSA-N

4,4'-Dimethylaminorex (abbreviated as 4,4'-DMAR), sometimes referred to by the street name "Serotoni", is a psychostimulant and entactogen designer drug related to aminorex, 4-methylaminorex, and pemoline. [3] It was first detected in the Netherlands in December 2012, [4] and has been sold as a designer drug around Europe since mid-2013.

Contents

4,4'-DMAR had been linked to at least 31 deaths in Hungary, Poland, and the UK by February 2014, mostly when consumed in combination with other drugs. [5] Nineteen deaths linked to 4,4'-DMAR were reported in Northern Ireland in the same time period. [6]

4,4'-DMAR acts as a potent and balanced serotonin-norepinephrine-dopamine releasing agent (SNDRA), with EC50 values for serotonin, norepinephrine, and dopamine release of 18.5 nM, 26.9 nM, and 8.6 nM, respectively. [3]

Legality

The UK Home Office expressed intent to ban 4,4'-DMAR following advice from the Advisory Council on the Misuse of Drugs [7] and subsequently it became a class A drug on 11 March 2015. [8]

4,4'-DMAR is an Anlage II controlled substance in Germany as of May 2015. [9]

Sweden's public health agency suggested to classify 4,4'-DMAR as hazardous substance on November 10, 2014. [10]

4,4'-DMAR is also banned in the Czech Republic. [11]

4,4'-DMAR is a Schedule I controlled substance in the US as of November 8, 2021. It only received two public comments during its public commenting period prior to being scheduled. [12] [13]

See also

Related Research Articles

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<span class="mw-page-title-main">Monoamine releasing agent</span> Class of compounds

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<span class="mw-page-title-main">Norepinephrine releasing agent</span> Catecholaminergic type of drug

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6-APB is an empathogenic psychoactive compound of the substituted benzofuran and substituted phenethylamine classes. 6-APB and other compounds are sometimes informally called "Benzofury" in newspaper reports. It is similar in structure to MDA, but differs in that the 3,4-methylenedioxyphenyl ring system has been replaced with a benzofuran ring. 6-APB is also the unsaturated benzofuran derivative of 6-APDB. It may appear as a tan grainy powder. While the drug never became particularly popular, it briefly entered the rave and underground clubbing scene in the UK before its sale and import were banned. It falls under the category of research chemicals, sometimes called "legal highs." Because 6-APB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to their popularity.

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

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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. 3,4-DMMC has been seized as a designer drug in Australia. 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.

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<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 a least one in large mammal study. 3-MMC is a monoamine transporter substrate that potently inhibits norepinephrine uptake and displays more pronounced dopaminergic vs. serotonergic activity.

<i>N</i>-Ethylhexedrone Chemical compound

N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.

<span class="mw-page-title-main">2C-B-aminorex</span> Chemical compound

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<span class="mw-page-title-main">4'-Fluoro-4-methylaminorex</span> Chemical compound

4'-Fluoro-4-methylaminorex is a recreational designer drug from the substituted aminorex family, with stimulant effects. It was first detected in Slovenia in 2018. It was made illegal in Italy in March 2020.

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

3',4'-Methylenedioxy-4-methylaminorex (MDMAR) is a recreational designer drug from the substituted aminorex family, with monoamine releasing effects.

References

  1. Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. "2021 - Placement of 4,4'-DMAR in Schedule I". www.deadiversion.usdoj.gov. Retrieved 2021-10-14.
  3. 1 2 Brandt SD, Baumann MH, Partilla JS, Kavanagh PV, Power JD, Talbot B, et al. (2014). "Characterization of a novel and potentially lethal designer drug (±)-cis-para-methyl-4-methylaminorex (4,4'-DMAR, or 'Serotoni')". Drug Testing and Analysis. 6 (7–8): 684–95. doi:10.1002/dta.1668. PMC   4128571 . PMID   24841869.
  4. "EMCDDA 2012 Annual report on the state of the drugs problem in Europe" (PDF). Archived (PDF) from the original on 2014-04-23. Retrieved 2014-04-21.
  5. "Risk Assessment Report of a new psychoactive substance: 4-methyl-5-(4-methylphenyl)-4,5-dihydrooxazol-2-amine (4,4′-dimethylaminorex, 4,4′-DMAR)" (PDF). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). November 2014. Archived (PDF) from the original on 2016-03-16. Retrieved 2016-02-11.
  6. "Unregulated stimulant drug blamed for 19 deaths, Belfast inquest told". The Guardian. 5 June 2014. Archived from the original on 8 February 2017. Retrieved 13 December 2016.
  7. "Letter to ACMD regarding advice on MT-45 and 4,4'-DMAR". UK Home Office. 26 November 2014. Archived from the original on 19 February 2015. Retrieved 19 February 2015.
  8. "Circular 003/2015: a change to the Misuse of Drugs Act 1971: control of MT-45 and 4,4'-DMAR". UK Home Office. 20 February 2015. Archived from the original on 2 April 2015. Retrieved 11 March 2015.
  9. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)" (in German). Archived from the original on 24 September 2015. Retrieved 29 June 2015.
  10. "Cannabinoider föreslås bli klassade som hälsofarlig vara" (in Swedish). Retrieved 29 June 2015.
  11. "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 (PDF) from the original on 2016-03-09. Retrieved 2016-02-06.
  12. "Federal Register :: Request Access".
  13. "2021 - Placement of 4,4'-DMAR in Schedule I".