4,4′-Dimethylaminorex

Summary

4,4′-Dimethylaminorex, commonly referred to as 4,4′-DMAR and colloquially known as “Serotonin,” belongs to the category of psychostimulant and entactogen designer drugs. This compound shares chemical similarities with aminorex, 4-methylaminorex, and pemoline. It was initially identified in the Netherlands in December 2012 and subsequently emerged in the European designer drug market around mid-2013.
By February 2014, 4,4′-DMAR had been associated with a minimum of 31 fatalities in Hungary, Poland, and the United Kingdom. The majority of these tragic incidents occurred when individuals consumed it in combination with other substances. Furthermore, during the same timeframe, Northern Ireland reported 19 deaths connected to the use of 4,4′-DMAR.
In terms of its pharmacological properties, 4,4′-DMAR functions as a potent and well-balanced serotonin-norepinephrine-dopamine-releasing agent (SNDRA). Its EC50 values for serotonin, norepinephrine, and dopamine release are 18.5 nM, 26.9 nM, and 8.6 nM, respectively.

Identifiers

IUPAC name
CAS Number	1445569-01-6
PubChem CID	20741615
ChemSpider	19546433
UNII	18Y239214S
Chemical and physical data
Formula	C11H14N2O
Molar mass	190.246 g·mol−1

Legality

The UK Home Office, acting on advice from the Advisory Council on the Misuse of Drugs, declared its intention to prohibit 4,4′-DMAR, ultimately classifying it as a class A drug on March 11, 2015.
In Germany, 4,4′-DMAR was designated as an Anlage II controlled substance as of May 2015.
On November 10, 2014, Sweden’s public health agency recommended categorizing 4,4′-DMAR as a hazardous substance.
The Czech Republic has also imposed a ban on 4,4′-DMAR.
In the United States, 4,4′-DMAR was categorized as a Schedule I controlled substance as of November 8, 2021, with only two public comments received during the preceding public commenting period.

FAQ

1. What is 4,4′-Dimethylaminorex (4,4′-DMAR)?

• 4,4′-Dimethylaminorex, also known as 4,4′-DMAR, is a synthetic compound classified as a psychostimulant and entactogen designer drug. It is chemically related to aminorex, 4-methylaminorex, and pemoline.

2. What are the street names for 4,4′-Dimethylaminorex?

• On the street, 4,4′-DMAR is sometimes referred to as “Serotonin.”

3. When and where was 4,4′-DMAR first detected?

• 4,4′-DMAR was first identified in the Netherlands in December 2012. It subsequently appeared in the designer drug market across Europe in mid-2013.

4. Has 4,4′-DMAR been associated with any health risks or fatalities?

• Yes, 4,4′-DMAR has been linked to a number of fatalities, particularly when used in combination with other substances. By February 2014, it had been associated with at least 31 deaths in Hungary, Poland, and the UK. Northern Ireland also reported 19 deaths related to its use during the same period.

5. What are the pharmacological effects of 4,4′-DMAR?

• 4,4′-DMAR acts as a potent serotonin-norepinephrine-dopamine-releasing agent (SNDRA). Its EC50 values for serotonin, norepinephrine, and dopamine release are 18.5 nM, 26.9 nM, and 8.6 nM, respectively.

6. How is 4,4′-Dimethylaminorex regulated internationally?

• The regulation of 4,4′-DMAR varies by country. For instance, it became a class A drug in the UK on March 11, 2015, following advice from the Advisory Council on the Misuse of Drugs. In Germany, it is classified as an Anlage II controlled substance as of May 2015. Sweden’s public health agency suggested classifying it as a hazardous substance on November 10, 2014. Additionally, 4,4′-DMAR is banned in the Czech Republic and classified as a Schedule I controlled substance in the United States as of November 8, 2021.

7. Are there any public comments or discussions related to the regulation of 4,4′-DMAR in the US?

• 4,4′-DMAR became a Schedule I controlled substance in the United States on November 8, 2021, with minimal public commentary or discussion during the scheduling process.

Please note that the use of 4,4′-Dimethylaminorex can be dangerous and is illegal in many places. It is important to prioritize safety and adhere to local laws and regulations regarding its use.

References

1. In 2021, 4,4′-DMAR was classified as a Schedule I substance in the United States. [Source: www.deadiversion.usdoj.gov, Retrieved 2021-10-14]
2. Anvisa, on July 24, 2023, published the Collegiate Board Resolution No. 804, which includes 4,4′-DMAR in the list of substances under special control. [Source: Diário Oficial da União, published 2023-07-25, Archived on 2023-08-27, Retrieved 2023-08-27]
3. A study by Brandt et al. in 2014 characterized 4,4′-DMAR as a potentially lethal designer drug known as ‘Serotoni.’ [Source: Drug Testing and Analysis, Volume 6 (7–8), 2014, doi:10.1002/dta.1668]
4. The European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) featured 4,4′-DMAR in its 2012 Annual Report on the drugs problem in Europe. [Source: EMCDDA 2012 Annual report on the state of the drugs problem in Europe, Archived PDF on 2014-04-23, Retrieved 2014-04-21]
5. In November 2014, the EMCDDA published a Risk Assessment Report on 4,4′-DMAR, a new psychoactive substance. [Source: EMCDDA, November 2014, Archived PDF on 2016-03-16, Retrieved 2016-02-11]
6. The Guardian reported on June 5, 2014, that an unregulated stimulant drug, 4,4′-DMAR, was linked to 19 deaths in Belfast. [Source: The Guardian, Archived from the original on 8 February 2017, Retrieved 13 December 2016]
7. The UK Home Office communicated with the Advisory Council on the Misuse of Drugs regarding advice on MT-45 and 4,4′-DMAR on November 26, 2014. [Source: UK Home Office, Archived from the original on 19 February 2015, Retrieved 19 February 2015]
8. Circular 003/2015 from the UK Home Office announced changes to the Misuse of Drugs Act 1971, including the control of MT-45 and 4,4′-DMAR, on February 20, 2015. [Source: UK Home Office, Archived from the original on 2 April 2015, Retrieved 11 March 2015]
9. 4,4′-DMAR was listed as an Anlage II controlled substance in Germany under the Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz – BtMG) as of May 2015. [Source: Gesetz über den Verkehr mit Betäubungsmitteln (BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel), Archived, Retrieved 29 June 2015]
10. Sweden’s health agency proposed classifying 4,4′-DMAR as a hazardous substance. [Source: In Swedish, Retrieved 29 June 2015]
11. The Czech Republic included 4,4′-DMAR in its list of psychotropic substances in 2016. [Source: In Czech, Archived PDF from the original on 2016-03-09, Retrieved 2016-02-06]
12. For more detailed information and official documents, you can refer to the Federal Register.