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Methiopropamine

Methiopropamine is a science 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 Methiopropamine rather than just read about it. In short: Methiopropamine (MPA), also known as N-methylthiopropamine, is an organic compound structurally related to methamphetamine. Originally reported in 1942, the molecule consists of a thiophene group with an alkyl amine substituent at the 2-position.

Methiopropamine — main illustration
Methiopropamine — illustration

Key takeaways

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

Reference excerpt

Methiopropamine (MPA), also known as N-methylthiopropamine, is an organic compound structurally related to methamphetamine. Originally reported in 1942, the molecule consists of a thiophene group with an alkyl amine substituent at the 2-position. It appeared for public sale in the United Kingdom in December 2010 as a "research chemical" or "legal high", recently branded as Blow. It has limited popularity as a recreational stimulant.

Pharmacology Methiopropamine functions as a norepinephrine–dopamine reuptake inhibitor (NDRI) that is approximately 1.85 times more selective for norepinephrine than dopamine. It is approximately one-third as potent as dextroamphetamine as a norepinephrine reuptake inhibitor and one-fifth as much as a dopamine reuptake inhibitor. It displays negligible activity as a serotonin reuptake inhibitor. Methiopropamine has the potential for significant acute toxicity with cardiovascular, gastrointestinal, and psychotic symptoms.

Metabolism

For N-alkyl amphetamines, deamination and N-dealkylation are the major elimination pathways and renal excretion is a minor one. Methiopropamine is metabolized into active thiopropamine, 4-hydroxymethiopropamine and thiophene S-oxides. These N-demethylated metabolites are further deaminated by the cytochrome P450 enzyme CYP2C19 in the liver transforming them into inactive 1-(thiophen-2-yl)-2-propan-2-one which can be seen as a phenylacetone derivative. Thiophene-2-carboxylic acid is the final major metabolic product. It is very hydrophilic and is excreted in urine. Methiopropamine and especially thiopropamine are also excreted renally, unchanged.

Synthesis There is a four-step synthesis of methiopropamine. It begins with (thiophen-2-yl)magnesium bromide, which is reacted with propylene oxide, yielding 1-(thiophen-2-yl)-2-hydroxypropane which is reacted with phosphorus tribromide, yielding 1-(thiophen-2-yl)-2-bromopropane which is finally reacted with methylamine, yielding 1-(thiophen-2-yl)-2-methylaminopropane. Methiopropamine is off-white, yellowish powder.

Legal status

China As of October 2015 MPA is a controlled substance in China.

Finland Methiopropamine is illegal in Finland, it is scheduled in "government decree on narcotic substances, preparations and plants".

Germany Methiopropamine is explicitly illegal in Germany.

United Kingdom Following the ban on ethylphenidate, authorities noticed an increase in methiopropamine use by injecting users. The ACMD suggested it be banned on 18 November 2015 as it had similar effects to ethylphenidate. The government enacted a temporary drug control order a week later which came into force on 27 November 2015. Though ordinarily the TCDO would only last 1 year, the ACMD reported that since its invocation prevalence of MPA had significantly decreased, and that it had been challenging to collect information about the drug. As a result of this, they requested that the TCDO be extended a further year. Methiopropanine was made a Class B controlled drug under the Misuse of Drugs Act 1971 (as amended) (Amendment)(No.2) Order 2017 [SI 2017/1114], this came into effect on the 27th of November 2017.

United States Methiopropamine is scheduled at the federal level in the United States. The DEA had planned to place methiopropamine in Schedule I of Controlled Substances and was accepting public comments until October 4, 2021. Later, the compound was placed in Schedule I.

Florida Methiopropamine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.

Tasmania (Australia) Methiopropamine is a "controlled substance" and therefore an "illegal drug" to import, possess or sell/traffic in without express authority of the relevant government agency.

See also 5-MMPA α-Pyrrolidinopentiothiophenone (α-PVT) Thiopropamine, demethylated counterpart Propylhexedrine, another ring substituted stimulant used as over-the-counter decongestant Thiothinone

References

External links Methiopropamine at erowid.org Methiopropamine at isomerdesign.com Methiopropamine at psychonautwiki.org

Illustrations

Methiopropamine illustration
Methiopropamine illustration
Methiopropamine: Methiopropamine metabolism is somewhat similar to methamphetamine. Hydroxylation, demethylation and deamination are in common. Formation of thiophene S-oxide is different, as is the end product which will probably be (substituted) thiophene-2-carboxylic acid. It is then excreted in urine. Compounds on red are inactive.
Methiopropamine metabolism is somewhat similar to methamphetamine. Hydroxylation, demethylation and deamination are in common. Formation of thiophene S-oxide is different, as is the end product which will probably be (substituted) thiophene-2-carboxylic acid. It is then excreted in urine. Compounds on red are inactive.
Methiopropamine: Four-step synthesis of racemic methiopropamine from (thiophen-2-yl)magnesium bromide.
Four-step synthesis of racemic methiopropamine from (thiophen-2-yl)magnesium bromide.

Worked examples

Example 1 — a first encounter with Methiopropamine

Start with the simplest possible case. Write down what Methiopropamine claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In science, 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 Methiopropamine 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 Methiopropamine 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 Methiopropamine

In research
Methiopropamine appears in science 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 Methiopropamine 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
Methiopropamine is common in secondary-school and first-year university syllabi. It links to neighbouring topics Designer drugs, Norepinephrine–dopamine reuptake inhibitors, Secondary amines, so understanding it makes those chapters shorter.
In everyday life
Look for Methiopropamine 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 Methiopropamine in 20 minutes

  1. Read the reference excerpt below once, without taking notes.
  2. Close the page and write down what Methiopropamine means in your own words.
  3. Compare your version with the excerpt and mark what you missed.
  4. Work through the three examples above with pen and paper.
  5. Explain Methiopropamine out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Methiopropamine in simple terms?

Methiopropamine (MPA), also known as N-methylthiopropamine, is an organic compound structurally related to methamphetamine. Originally reported in 1942, the molecule consists of a thiophene group with an alkyl amine substituent at the 2-position.

Why does Methiopropamine matter?

Because it connects several science 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 Methiopropamine?

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 Methiopropamine.

Tags

  • Designer drugs
  • Norepinephrine–dopamine reuptake inhibitors
  • Secondary amines
  • Stimulants
  • Thiopropamines

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