chemistry

N-Methylmescaline

N-Methylmescaline 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 N-Methylmescaline rather than just read about it. In short: N-Methylmescaline (NMM), also known as methylmescaline (M-M), is a serotonin receptor modulator of the phenethylamine alkaloid family related to mescaline that occurs naturally in the cacti species Lophophora williamsii, Pelecyphora aselliformis, and Pachycereus pringlei, among others. Use and effects According to chemist Alexander Shulgin, N-methylmescaline shows no central or peripheral effects at doses of ~25 mil…

Key takeaways

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

Reference excerpt

N-Methylmescaline (NMM), also known as methylmescaline (M-M), is a serotonin receptor modulator of the phenethylamine alkaloid family related to mescaline that occurs naturally in the cacti species Lophophora williamsii, Pelecyphora aselliformis, and Pachycereus pringlei, among others.

Use and effects

According to chemist Alexander Shulgin, N-methylmescaline shows no central or peripheral effects at doses of ~25 milligrams, which is many times the minor or trace amounts present in peyote. Nonetheless, according to Shulgin, N-methylmescaline, in combination with potent isoquinoline monoamine oxidase inhibitors (MAOIs) that are also present in the cactus, might be the active psychedelic constituent of Pachycereus pringlei, which notably does not contain mescaline.

Interactions

Pharmacology

Pharmacodynamics N-Methylmescaline shows weak affinity for serotonin receptors similarly to mescaline. It was found to have about half the serotonin receptor affinity of mescaline (A2 = 5,250 nM vs. 2,240 nM, respectively). N-Methylmescaline failed to significantly substitute for mescaline (25 mg/kg) in rodent drug discrimination tests either with intraperitoneal or intracerebroventricular injection. In contrast to N-methylmescaline however, trichocereine (N,N-dimethylmescaline) produced similar effects to mescaline at a dose of 50 mg/kg intraperitoneally, whereas it only transiently substituted for mescaline when given intracerebroventricularly. Trichocereine has also been reported to be psychedelic in humans, although findings in this area are controversial and conflicting. It has been noted that N-methylation of psychedelic phenethylamines, for instance Beatrice (N-methyl-DOM), has invariably eliminated their hallucinogenic activity. N-Methylmescaline is less toxic than mescaline in terms of raw LD50.

Chemistry N-Methylmescaline, also known as N-methyl-3,4,5-trimethoxyphenethylamine, is a substituted phenethylamine and scaline. It is specifically the N-methyl analogue of mescaline (3,4,5-trimethoxyphenethylamine).

Synthesis The chemical synthesis of N-methylmescaline has been described.

Analogues Analogues of N-methylmescaline, besides mescaline, include trichocereine (N,N-dimethylmescaline), N-acetylmescaline, N-formylmescaline, and N,N-diformylmescaline, among others. Other psychedelic-related N-methylphenethylamines include methyl-TMA (N-methyl-TMA), Beatrice (N-methyl-DOM), N-methyl-DOET, N-methyl-DOB, N-methyl-2C-I, N-methyl-DMA, N-methyl-MMDA-2, and MDMA (N-methyl-MDA).

History N-Methylmescaline was first described in the scientific literature by Ernst Späth and Johann Bruck in 1937. It was isolated from Lophophora williamsii (peyote) by the researchers and was also synthesized.

Society and culture

Legal status

Canada N-Methylmescaline is not a controlled substance in Canada as of 2025.

United States N-Methylmescaline is not an explicitly controlled substance in the United States. However, it may be considered controlled in this country as it is a positional isomer of 3,4,5-trimethoxyamphetamine (TMA), which is a specifically regulated substance.

See also Scaline Pachycereus pringlei § Constituents and effects

References

External links N-Methylmescaline - Isomer Design N-Methylmescaline - The Shulgin Index N-Methylmescaline - Trout's Notes

Illustrations

Worked examples

Example 1 — a first encounter with N-Methylmescaline

Start with the simplest possible case. Write down what N-Methylmescaline 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 N-Methylmescaline 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 N-Methylmescaline 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 N-Methylmescaline

In research: N-Methylmescaline 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 N-Methylmescaline 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: N-Methylmescaline is common in secondary-school and first-year university syllabi. It links to neighbouring topics Alexander Shulgin, Lophophora alkaloids, Methyl compounds, so understanding it makes those chapters shorter.
In everyday life: Look for N-Methylmescaline 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 N-Methylmescaline in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what N-Methylmescaline 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 N-Methylmescaline out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is N-Methylmescaline in simple terms?

Why does N-Methylmescaline 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 N-Methylmescaline?

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 N-Methylmescaline.