chemistry

MME (drug)

MME (drug) 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 MME (drug) rather than just read about it. In short: MME, also known as 2,4-dimethoxy-5-ethoxyamphetamine or as TMA2-5-EtO, is a psychoactive drug of the phenethylamine, amphetamine, and DOx families related to TMA-2. It is the analogue of TMA-2 in which the methoxy group at the 5 position has been replaced with an ethoxy group.

Key takeaways

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

Reference excerpt

MME, also known as 2,4-dimethoxy-5-ethoxyamphetamine or as TMA2-5-EtO, is a psychoactive drug of the phenethylamine, amphetamine, and DOx families related to TMA-2. It is the analogue of TMA-2 in which the methoxy group at the 5 position has been replaced with an ethoxy group.

Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MME's dose as 40 mg and above orally and its duration as probably 6 to 10 hours. MME received a "plus-two" rating on the Shulgin Rating Scale. However, its specific effects were not described, aside from diarrhea and beyond statements like it having "a possibly interesting collection of effects" and it being "very encouraging". Moreover, Shulgin stated that it was less active than MEM, another related TMA-2 analogue. Shulgin expressed interest in further evaluating higher doses of MME.

Interactions

Pharmacology

Pharmacodynamics Alexander Shulgin describes in PiHKAL an experiment with MME, in which he administered varying amounts of the drug to mice via injections. Shulgin reports that 7 of the 9 mice injected with MME died as a result. After describing his experiment, Shulgin speculates that MME may have an LD50 value of around 60–80 mg/Kg in mice when injected. Shulgin describes that one of the mice began convulsing after being administered MME: "[...] the mouse went into a twitching series of convulsions (known as clonic in the trade) and in five minutes he was dead."

Chemistry

Synthesis Shulgin describes the synthesis of MME in his book PiHKAL. He starts with 4-ethoxy-3-methoxybenzaldehyde. Shulgin labels the 4-ethoxy-3-methoxybenzaldehyde as ethylvanillin, although ethylvanillin is in fact 3-ethoxy-4-hydroxybenzaldehyde. Ethylvanillin can be methylate to 4-ethoxy-3-methoxybenzladehyde. The 4-ethoxy-3-methoxybenzaldehyde is then subjected to a Baeyer–Villiger oxidation with peracetic acid and acetic acid to yield 4-ethoxy-3-methoxyphenol. The 4-ethoxy-3-methoxyphenol is methylated to yield 2,4-dimethoxy-1-ethoxybenzene. The 2,4-dimethoxy-1-ethoxybenzene is subjected to Reimer-Tiemann formylated to 2,4-dimethoxy-5-ethoxybenzaldehyde. The 2,4-dimethoxy-5-ethoxybenzaldehyde by subjecting it to a Knoevenagel condensation with acetic acid, ammonium acetate and nitroethane, and reducing the resulting 1-(2,4-dimethoxy-5-ethoxyphenyl)-2-nitropropene to MME with lithium aluminium hydride under an inert atmosphere.

Analogues MME has several isomers. MEM is one of them along with EMM. According to Alexander Shulgin, EEM is not active. MEM is active in humans and also possesses activity at the serotonin 5-HT2A receptor. Other analogues of MME include Iris (DOM-5-EtO) and metaescaline.

History MME was first described in the scientific literature by Alexander Shulgin in 1968. Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.

See also DOx (psychedelics) TWEETIO § DOx compounds EMM and MEM

References

External links MME - Isomer Design MME - PiHKAL - Erowid MME - PiHKAL - Isomer Design

Illustrations

Worked examples

Example 1 — a first encounter with MME (drug)

Start with the simplest possible case. Write down what MME (drug) 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 MME (drug) 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 MME (drug) 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 MME (drug)

In research: MME (drug) 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 MME (drug) 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: MME (drug) is common in secondary-school and first-year university syllabi. It links to neighbouring topics Drugs not assigned an ATC code, Ethoxy compounds, Methoxy compounds, so understanding it makes those chapters shorter.
In everyday life: Look for MME (drug) 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 MME (drug) in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what MME (drug) 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.
Explain MME (drug) out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is MME (drug) in simple terms?

Why does MME (drug) 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 MME (drug)?

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 MME (drug).