4,4'-Dimethylaminorex

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.

4,4'-Dimethylaminorex
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
FormulaC11H14N2O
Molar mass190.246 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'-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

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. 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".
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