Chemistry:4,4'-Dimethylaminorex

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Short description: Chemical compound
4,4'-Dimethylaminorex
4,4'-Dimethylaminorex.svg
Clinical data
Other names4,4'-DMAR
ATC code
  • none
Legal status
Legal status
  • BR: F2
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class A
  • US: Schedule I[1]
  • Illegal in Czech Republic and Sweden
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)

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.[2] It was first detected in the Netherlands in December 2012,[3] and has been sold as a designer drug around Europe since mid-2013.

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.[4] Nineteen deaths linked to 4,4'-DMAR were reported in Northern Ireland in the same time period.[5]

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.[2]

Legality

The UK Home Office expressed intent to ban 4,4'-DMAR following advice from the Advisory Council on the Misuse of Drugs[6] and subsequently it became a class A drug on 11 March 2015.[7]

4,4'-DMAR is an Anlage II controlled substance in Germany (As of May 2015).[8]

Sweden's public health agency suggested to classify 4,4'-DMAR as hazardous substance on November 10, 2014.[9]

4,4'-DMAR is also banned in the Czech Republic.[10]

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.[11][12]

See also

References

  1. ↑ "2021 - Placement of 4,4'-DMAR in Schedule I". https://www.deadiversion.usdoj.gov/fed_regs/rules/2021/fr0812_7.htm. 
  2. ↑ 2.0 2.1 "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. 2014. doi:10.1002/dta.1668. PMID 24841869. 
  3. ↑ "EMCDDA 2012 Annual report on the state of the drugs problem in Europe". http://www.emcdda.europa.eu/attachements.cfm/att_190854_EN_TDAC12001ENC_.pdf. 
  4. ↑ "Risk Assessment Report of a new psychoactive substance: 4-methyl-5-(4-methylphenyl)-4,5-dihydrooxazol-2-amine (4,4′-dimethylaminorex, 4,4′-DMAR)". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). November 2014. http://www.emcdda.europa.eu/system/files/publications/931/4%2C4'-DMAR%20Risk%20Assessment%20Report.pdf. 
  5. ↑ "Unregulated stimulant drug blamed for 19 deaths, Belfast inquest told.". The Guardian. 5 June 2014. https://www.theguardian.com/society/2014/jun/05/unregulated-stimulant-drug-blamed-19-deaths-belfast-inquest. 
  6. ↑ "Letter to ACMD regarding advice on MT-45 and 4,4'-DMAR". UK Home Office. 26 November 2014. https://www.gov.uk/government/publications/letter-to-acmd-regarding-advice-on-mt-45-and-44-dmar. 
  7. ↑ "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. https://www.gov.uk/government/publications/circular-0032015-a-change-to-the-misuse-of-drugs-act-1971-control-of-mt-45-and-44-dmar. 
  8. ↑ "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)" (in German). http://www.gesetze-im-internet.de/btmg_1981/anlage_ii.html. 
  9. ↑ "Cannabinoider föreslås bli klassade som hälsofarlig vara" (in Swedish). http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/november/cannabinoider-foreslas-bli-klassade-som-halsofarlig-vara/. 
  10. ↑ "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (in Czech). Ministerstvo zdravotnictví. http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf. 
  11. ↑ "Federal Register :: Request Access". https://www.ecfr.gov/current/title-21/chapter-II/part-1308/subject-group-ECFRf62f8e189108c4d/section-1308.11. 
  12. ↑ "2021 - Placement of 4,4'-DMAR in Schedule I". https://www.deadiversion.usdoj.gov/fed_regs/rules/2021/fr0812_7.htm. 



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