4,4'-Dimethylaminorex

4,4'-Dimethylaminorex
Clinical data
Other names	4,4'-DMAR
ATC code	none;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); DE: Anlage II (Authorized trade only, not prescriptible); UK: Class A; US: Schedule I; 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 ;
PubChem CID	20741615;
ChemSpider	19546433;
UNII	18Y239214S;
KEGG	C22805;
CompTox Dashboard (EPA)	DTXSID901031562 ;
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'-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'-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^[update].^[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]

References

^ "2021 - Placement of 4,4'-DMAR in Schedule I". www.deadiversion.usdoj.gov. Retrieved 2021-10-14.
^ 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.
^ ^a ^b 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.
^ "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.
^ "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.
^ "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.
^ "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.
^ "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.
^ "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.
^ "Cannabinoider föreslås bli klassade som hälsofarlig vara" (in Swedish). Retrieved 29 June 2015.
^ "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.
^ "Federal Register :: Request Access".
^ "2021 - Placement of 4,4'-DMAR in Schedule I".

[1] "2021 - Placement of 4,4'-DMAR in Schedule I". www.deadiversion.usdoj.gov. Retrieved 2021-10-14.

[2] 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.

[BrandtBaumann2014-3] 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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4,4'-Dimethylaminorex

Legality

See also

References