para-Methoxy-N-methylamphetamine

para-Methoxy-N-methylamphetamine

Legal status
Legal status	CA: Schedule I DE: Anlage I (Controlled) UK: Class A US: Controlled under Federal Analogue Act
Identifiers
IUPAC name 1-(4-Methoxyphenyl)-N-methylpropan-2-amine
CAS Number	22331-70-0 Y
PubChem (CID)	90766
ChemSpider	81951
UNII	037U5SR9KL Y
ECHA InfoCard	100.020.242
Chemical and physical data
Formula	C11H17NO
Molar mass	179.259 g/mol
3D model (Jmol)	Interactive image
SMILES CC(CC1=CC=C(C=C1)OC)NC C1=CC(=CC=C1CC(C)NC)OC
InChI InChI=1S/C11H17NO/c1-9(12-2)8-10-4-6-11(13-3)7-5-10/h4-7,9,12H,8H2,1-3H3 Key:UGFMBZYKVQSQFX-UHFFFAOYSA-N
(verify)

para-Methoxy-N-methylamphetamine (also known as PMMA, Red Mitsubishi), chemically known as methyl-MA, 4-methoxy-N-methylamphetamine, 4-MMA) or (4-PMDA, as listed to its original physical name.) is a stimulant and psychedelic drug closely related to the amphetamine-class serotonergic drug para-methoxyamphetamine (PMA). PMMA is the 4-methoxy analog of methamphetamine. Little is known about the pharmacological properties, metabolism, and toxicity of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose.^[1] In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.^[2]

Its effects in humans are reputedly similar to those of PMA, but slightly more empathogenic in nature. It has a reduced tendency to produce severe hyperthermia at low dosages,^[3][4] but at higher dosages side effects and risk of death becomes similar to those of PMA.^[5]

The synthesis and effects of PMMA were described by American experimental chemist Alexander Shulgin in his book PiHKAL, where it is referred to by the name "methyl-MA", as the N-methylated form of 4-MA (PMA). Shulgin reported that PMMA produces an increase in blood pressure and in heart rate, at doses above 100 mg, but causes no psychoactive effects at these levels.

Recreational use

Tablets of PMMA recovered by the U.S. Drug Enforcement Administration

PMMA has been found in tablets and capsules of the MDMA sold as "ecstasy". A number of deaths have been attributed to tablets sold as ecstasy that contained other substances, such as PMMA's structural analog, PMA.^[6][7] Death can occur when an ecstasy user believes they are consuming recreational doses of MDMA, when they are in fact consuming a lethal dose of another substance with similar effects. PMA is of particular concern because it not only causes a release of serotonin but also acts as a monoamine oxidase inhibitor (MAOI); if it is used in combination with MDMA or another MDMA-like substance, serotonin syndrome can result.^[8]

PMMA can be detected with pill testing kits.

Deaths

In January 2011, the Norwegian Broadcasting Corporation reported that Norway had seen 12 deaths related to PMMA over the course of 6 months. In March 2011, Dutch media reported that there had been 4 deaths in the province of Limburg since November 2010.^[9] In April 2011, Icelandic media reported the death of a young woman that may have been connected to PMMA.

In 2011, 4 deaths were recorded in Scotland as a result of ecstasy tablets which also contained PMMA.^[10]

In January 2012, a number of ecstasy-related deaths in Canada in the previous year were linked to PMMA overdoses.^{[11][12][13][14][15][16]}

In September 2012, the deaths of two men in County Cork, Ireland, have been linked to PMMA overdoses.^[17] In the same month, the death of a man in Queensland, Australia was attributed to PMMA.^[18]

In December 2012 and January 2013, several deaths were linked to PMMA in the UK.^[19]

In June 2013 a PMMA-related death occurred in the Dutch city of 's-Hertogenbosch.^[20] Two months later, In August 2013, another possibly PMMA-related death occurred in the nearby town of Sliedrecht.^[21][22][23]

In January 2015 in the UK four people died, suspected of taking ecstasy containing PMMA.^[24] In the same month, in Sweden, another man died from ecstasy laced with PMMA.^[25]

In May 2015 a young woman died in Dublin, Ireland, after taking what is suspected to be PMMA.^[26]

In April 2016 four young Argentines and one Uruguayan died during a massive rave called "Time Warp" in Buenos Aires and five more were hospitalized. PMMA was found in their bodies. ^[27]

Legal status

United States

PMMA is not scheduled at the federal level in the United States,^[28] but could be considered an analog (of PMA), in which case, sales or possession intended for human consumption could be prosecuted under the Federal Analog Act.

Florida

PMMA is a Schedule I controlled substance in the state of Florida, listed as "4-methoxymethamphetamine", making it illegal to buy, sell, or possess in Florida.^[29]

United Kingdom

PMMA is controlled as a Schedule 1, Class A drug in the UK.

See also

• para-Methoxyamphetamine (PMA)
• 2-Methoxymethamphetamine (Methoxyphenamine)
• 3-Methoxymethamphetamine (MMMA)
• 4-Fluoromethamphetamine (4-FMA)
• 4-Methylmethamphetamine (4-MMA)
• 4-Methoxymethcathinone (bk-PMMA)
• Venlafaxine

References

External links

• Methyl-MA entry in PiHKAL
• Methyl-MA entry in PiHKAL • info
• Dutch article by TRIMBOS institute from 31-03-2011
• Icelandic arictle by Mbl news(Mbl.is) from 30-04-2011