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.[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'-Dimethylaminorex

Clinical data
Other names	4,4'-DMAR
ATC code	none
Legal status
Legal status	DE: Anlage II (Authorized trade only, not prescriptible) UK: Class A US: Schedule I Proposed[1] Illegal in Czech Republic and Sweden
Identifiers
IUPAC name 4-Methyl-5-(4-methylphenyl)-4,5-dihydro-1,3-oxazol-2-amine
CAS Number	1445569-01-6^Y
PubChem CID	20741615
ChemSpider	19546433
UNII	18Y239214S
Chemical and physical data
Formula	C11H14N2O
Molar mass	190.246 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(N=C(N)O1)C1C2=CC=C(C)C=C2
InChI 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.[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]

References

1. "Schedules of Controlled Substances: Placement of 4,4′-DMAR in Schedule I". Federal Register. 7 April 2020.
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.
3. EMCDDA 2012 Annual report on the state of the drugs problem in Europe
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)" (PDF). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). November 2014.
5. "Unregulated stimulant drug blamed for 19 deaths, Belfast inquest told". The Guardian. 5 June 2014.
6. "Letter to ACMD regarding advice on MT-45 and 4,4'-DMAR". UK Home Office. 26 November 2014. Retrieved 19 February 2015.
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. Retrieved 11 March 2015.
8. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)" (in German). Retrieved 29 June 2015.
9. "Cannabinoider föreslås bli klassade som hälsofarlig vara" (in Swedish). Retrieved 29 June 2015.
10. "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.