chemistry

Para-Methoxymethamphetamine

Para-Methoxymethamphetamine is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Para-Methoxymethamphetamine rather than just read about it. In short: para-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA), is a serotonergic drug of the amphetamine family related to para-methoxyamphetamine (PMA). It is the 4-methoxy analogue of methamphetamine.

Key takeaways

Para-Methoxymethamphetamine belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Para-Methoxymethamphetamine to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Para-Methoxymethamphetamine from memory before moving on to harder problems.

Reference excerpt

para-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA), is a serotonergic drug of the amphetamine family related to para-methoxyamphetamine (PMA). It is the 4-methoxy analogue 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. In the early 2010s, a number of deaths in users of the drug MDMA (ecstasy) were linked to misrepresented tablets and capsules of PMMA. PMMA is a serotonin–norepinephrine releasing agent (SNRA) as well as potent monoamine oxidase inhibitor (MAOI). It has a reduced tendency to produce severe hyperthermia at low doses compared to PMA, but at higher doses, side effects and risk of death become similar to those of PMA. 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).

Use and effects According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), the effects of PMMA at a dose of 110 mg orally included tachycardia, compulsive yawning, and nystagmus, among others. It was said to have some of the physical side effects of the entactogen MDMA but none of its central effects. No psychedelic-like effects were mentioned.

Pharmacology

Pharmacodynamics PMMA is a monoamine releasing agent (MRA). The drug's EC50Tooltip half-maximal effective concentration values for induction of monoamine release in rat brain synaptosomes have been reported for the individual enantiomers of PMMA. In the case of (S)-PMMA, they were 41 nM for serotonin, 147 nM for norepinephrine, and 1,000 nM for dopamine, whereas for (R)-PMMA, they were 134 nM for serotonin, >14,000 nM for norepinephrine, and 1,600 nM for dopamine. Hence, PMMA appears to be a serotonin–norepinephrine releasing agent (SNRA) with weak effects on dopamine release. The drug has been found to strongly release serotonin and to weakly release dopamine in the brain in rodents in vivo. In addition to its MRA activity, PMMA is a potent monoamine oxidase A (MAO-A) inhibitor. Its IC50Tooltip half-maximal inhibitory concentration for MAO-A inhibition has been reported to be 1,700 nM. This is several-fold less potent than the related agents para-methoxyamphetamine (PMA) and 4-methylthioamphetamine (4-MTA). PMMA is said to lack affinity for the serotonin 5-HT2A receptor. In one study, its affinities were >20,000 nM for the serotonin 5-HT1A receptor, 13,600 nM for the serotonin 5-HT2A receptor, and >13,000 nM for the serotonin 5-HT2C receptor. On the other hand, PMMA shows much higher affinities for the mouse and rat trace amine-associated receptor 1 (TAAR1). In rodents, PMMA produces hyperlocomotion, no changes in locomotor activity, and/or catatonia, and has effects that are said to differ from those of amphetamine-like stimulants. It has been said not to have amphetamine-like properties in rodents even at high doses. Similarly, PMMA did not substitute for the psychedelic DOM. On the other hand, in contrast to PMA, PMMA fully substituted for MDMA in drug discrimination tests in rodents, despite not having MDMA-like psychoactive effects in humans. In any case, PMMA is said to lack the amphetamine- or stimulant-like properties of MDMA.

Chemistry

Synthesis The chemical synthesis of PMMA has been described.

Detection PMMA can be detected with reagent testing kits.

Analogues Analogues of PMMA include para-methoxyamphetamine (PMA), para-methoxy-N-ethylamphetamine (PMEA), 4-methylthio-N-methylamphetamine (4-MTMA), 4-methyl-N-methylamphetamine (4-MMA; mephedrine), para-chloro-N-methylamphetamine (PCMA), 4-fluoro-N-methylamphetamine (4-FMA), methoxyphenamine (2-methoxy-N-methylamphetamine; OMMA), 3-methoxy-N-methylamphetamine (MMMA), and methedrone (4-methoxymethcathinone; bk-PMMA), among others.

History PMMA was first described in the scientific literature by at least 1984.

Society and culture

Recreational use

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. 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.

Deaths In January 2011, the Norwegian Broadcasting Corporation reported that Norway had seen 12 deaths related to PMMA over the course of six months. In March 2011, Dutch media reported that there had been four deaths in the province of Limburg since November 2010. In April 2011, Icelandic media reported the death of a young woman that may have been connected to PMMA. In 2011, four deaths were recorded in Scotland as a result of ecstasy tablets which also contained PMMA. In January 2012, a number of ecstasy-related deaths in Canada in the previous year were linked to PMMA overdoses. In the single year, approximately 45 exposures occurred, resulting in 21 deaths. Cases were centred primarily in Calgary and Vancouver. In September 2012, the deaths of two men in County Cork, Ireland, have been linked to PMMA overdoses. In the same month, the death of a man in Queensland, Australia was attributed to PMMA. In June 2013 a PMMA-related death occurred in the Dutch city of 's-Hertogenbosch. Two months later, In August 2013, another possibly PMMA-related death occurred in the nearby town of Sliedrecht. In January 2015 in the UK four people died, suspected of taking ecstasy containing PMMA. In the same month, in Sweden, another man died from ecstasy laced with PMMA. In May 2015 a young woman died in Dublin, Ireland, after taking what is suspected to be PMMA. 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.

Legal status

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

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Illustrations

Para-Methoxymethamphetamine: Tablets of PMMA recovered by the U.S. Drug Enforcement Administration — Tablets of PMMA recovered by the U.S. Drug Enforcement Administration

Worked examples

Example 1 — a first encounter with Para-Methoxymethamphetamine

Start with the simplest possible case. Write down what Para-Methoxymethamphetamine claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Para-Methoxymethamphetamine before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Para-Methoxymethamphetamine ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Para-Methoxymethamphetamine

In research: Para-Methoxymethamphetamine appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Para-Methoxymethamphetamine in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Para-Methoxymethamphetamine is common in secondary-school and first-year university syllabi. It links to neighbouring topics 4-Methoxyphenyl compounds, Designer drugs, Methamphetamines, so understanding it makes those chapters shorter.
In everyday life: Look for Para-Methoxymethamphetamine outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Para-Methoxymethamphetamine in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Para-Methoxymethamphetamine means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
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Frequently asked questions

What is Para-Methoxymethamphetamine in simple terms?

Why does Para-Methoxymethamphetamine matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Para-Methoxymethamphetamine?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Para-Methoxymethamphetamine.