chemistry

Scaline

Scaline 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 Scaline rather than just read about it. In short: A scaline, also known as a substituted mescaline analogue and typically but not always a 4-substituted 3,5-dimethoxyphenethylamine, is an analogue of the phenethylamine serotonergic psychedelic mescaline (3,4,5-trimethoxyphenethylamine). Other related compounds include the 2C (4-substituted 2,5-dimethoxyphenethylamine) and DOx (4-substituted 2,5-dimethoxyamphetamine) compounds as well as 3,4,5-trimethoxyamphetamine…

Key takeaways

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

Reference excerpt

A scaline, also known as a substituted mescaline analogue and typically but not always a 4-substituted 3,5-dimethoxyphenethylamine, is an analogue of the phenethylamine serotonergic psychedelic mescaline (3,4,5-trimethoxyphenethylamine). Other related compounds include the 2C (4-substituted 2,5-dimethoxyphenethylamine) and DOx (4-substituted 2,5-dimethoxyamphetamine) compounds as well as 3,4,5-trimethoxyamphetamine (TMA) and other 4-substituted 3,5-dimethoxyamphetamines (3C drugs). They are also mescaline analogues, but the 2C and DOx drugs have a methoxy group at the 2 position instead of the 3 position of the phenyl ring, while TMA is an amphetamine rather than a phenethylamine. The pharmacology of mescaline analogues has been studied. Mescaline analogues, or 4-substituted 3,5-dimethoxyphenethylamines specifically, tend to be much less potent than the 2C and DOx drugs. This relates to the fact that the 2,4,5-substitution pattern tends to be optimal in terms of receptor affinity and potency. However, mescaline analogues are frequently much more potent than mescaline. Substituted mescaline analogues have been extensively characterized by Alexander Shulgin and described in his books such as PiHKAL (Phenethylamines I Have Known and Loved) and The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds as well as in his literature reviews. They have also been studied by David E. Nichols and Daniel Trachsel, among other researchers. A closely related group is thioscalines, which are compounds in which one or more of the methoxy groups of mescaline are replaced with alkylthio groups.

Use and effects

Interactions

Pharmacology

Pharmacodynamics

Society and culture

Legal status

Canada Mescaline and 3,4,5-trimethoxyamphetamine (TMA) are the only scalines (and derivatives) that are controlled substances in Canada as of 2025.

List of scalines

4-Substituted

4-Alkoxy-substituted 4-Methoxyescaline (4-MeO-E; MeOEtO) (3,5-dimethoxy-4-(2-methoxyethoxy)phenethylamine) Allylescaline (AL) (4-allyloxy-3,5-dimethoxyphenethylamine) Amylescaline (4-n-amyloxy-3,5-dimethoxyphenethylamine) Benzscaline (BZ) (4-benzyloxy-3,5-dimethoxyphenethylamine) Buscaline (B) (4-butoxy-3,5-dimethoxyphenethylamine) Cyclopropylmescaline (CPM) (4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine) Cycloproscaline (CP) (4-cyclopropoxy-3,5-dimethoxyphenethylamine) Difluoroescaline (DFE) (multiple forms) Difluoroisoproscaline (DFIP) (multiple forms) Difluoromescaline (DFM) (4-difluoromethoxy-3,5-dimethoxyphenethylamine) Escaline (E) (4-ethoxy-3,5-dimethoxyphenethylamine) Fluoroescaline (FE) (multiple forms) Fluoromescaline (FM) (4-fluoromethoxy-3,5-dimethoxyphenethylamine) Fluoroproscaline (FP) (multiple forms) Hexylescaline (4-n-hexyloxy-3,5-dimethoxyphenethylamine) Isobuscaline (IB) (4-isobutoxy-3,5-dimethoxyphenethylamine) Isoproscaline (IP) (4-isopropoxy-3,5-dimethoxyphenethylamine) Methallylescaline (MAL) (4-methylallyloxy-3,5-dimethoxyphenethylamine) Phenescaline (4-phenylethoxy-3,5-dimethoxyphenethylamine) Phescaline (4-phenoxy-3,5-dimethoxyphenethylamine) Propynylscaline (4-propynyloxy-3,5-dimethoxyphenethylamine) Proscaline (P) (4-propoxy-3,5-dimethoxyphenethylamine) Septylescaline (4-n-heptyloxy-3,5-dimethoxyphenethylamine) Trifluoroescaline (TFE) (multiple forms) Trifluoromescaline (TFM) (4-trifluoromethoxy-3,5-dimethoxyphenethylamine) Trifluoroproscaline (TFP) (multiple forms) Viscaline (4-vinyl-3,5-dimethoxyphenethylamine)

4-Alkylthio-substituted 4-Thiobuscaline (4-TB) (4-butylthio-3,5-dimethoxyphenethylamine) 4-Thioescaline (4-TE) (4-ethylthio-3,5-dimethoxyphenethylamine) 4-Thiomescaline (4-TM) (4-methylthio-3,5-dimethoxyphenethylamine) 4-Thioproscaline (4-TP) (4-propylthio-3,5-dimethoxyphenethylamine)

Others Biscaline (4-phenyl-3,5-dimethoxyphenethylamine) 4-Bromomescaline (4-Br-3,5-DMPEA) (4-bromo-3,5-dimethoxyphenethylamine) 4-Desmethylmescaline (desmethyl) (4-hydroxy-3,5-dimethoxyphenethylamine) 4-Desoxymescaline (desoxy) (4-methyl-3,5-dimethoxyphenethylamine)

3- or 5-Extended

Asymbescaline (ASB) (3,4-diethoxy-5-methoxyphenethylamine) Metadifluoromescaline (MDFM) (3,4-dimethoxy-5-difluoromethoxyphenethylamine) Metaescaline (ME) (3-ethoxy-4,5-dimethoxyphenethylamine) Metaproscaline (MP) (3,4-dimethoxy-5-propoxyphenethylamine) Symbescaline (SB) (4-methoxy-3,5-diethoxyphenethylamine) 4-Thioasymbescaline (4-TASB) (4-ethylthio-3-ethoxy-5-methoxyphenethylamine) 4-Thiometaescaline (4-TME) (4-methylthio-3-ethoxy-5-methoxyphenethylamine) 4-Thiosymbescaline (4-TSB) (4-methylthio-3,5-diethoxyphenethylamine) 4-Thiotrescaline (4-T-TRIS; 4-thiotrisescaline) (4-ethylthio-3,5-diethoxyphenethylamine) Trescaline (TRIS; trisescaline) (3,4,5-triethoxyphenethylamine)

3- or 5-Replaced 3-Desmethylmescaline (3-DESMETHYL) (3,4-dimethoxy-5-hydroxyphenethylamine) 3-Thioasymbescaline (3-TASB) (3-ethylthio-4-ethoxy-5-methoxyphenethylamine) 5-Thioasymbescaline (5-TASB) (3,4-diethoxy-5-methylthiophenethylamine) 3-Thioescaline (3-TE) (3-methoxy-4-ethoxy-5-methylthiophenethylamine) 3-Thiomescaline (3-TM) (3,4-dimethoxy-5-methylthiophenethylamine) 3-Thiometaescaline (3-TME) (3-ethylthio-4,5-dimethoxyphenethylamine) 5-Thiometaescaline (5-TME) (3-ethoxy-4-methoxy-5-methylthiophenethylamine) 3-Thiosymbescaline (3-TSB) (3-ethoxy-4-methoxy-5-ethylthiophenethylamine) 3-Thiotrescaline (3-T-TRIS; 3-thiotrisescaline) (3,4-diethoxy-5-ethylthiophenethylamine) 3,4,5-Trideoxymescaline (TMePEA) (3,4,5-trimethylphenethylamine)

2- or 6-Substituted 2-Bromo-6-chloromescaline (2-bromo-6-chloro-3,4,5-trimethoxyphenethylamine) 2-Bromo-6-methylmescaline (2-bromo-6-methyl-3,4,5-trimethoxyphenethylamine) 2-Bromomescaline (2-bromo-3,4,5-trimethoxyphenethylamine) 2-Chloromescaline (2-chloro-3,4,5-trimethoxyphenethylamine) 2-Iodomescaline (2-iodo-3,4,5-trimethoxyphenethylamine) 2-Methylmescaline (2-methyl-3,4,5-trimethoxyphenethylamine) 2,6-Dibromomescaline (2,6-dibromo-3,4,5-trimethoxyphenethylamine) 2,6-Dichloromescaline (2,6-dichloro-3,4,5-trimethoxyphenethylamine) 2,6-Dimethylmescaline (2,6-dimethyl-3,4,5-trimethoxyphenethylamine) 2,3,4,5,6-Pentamethoxyphenethylamine (PeMPEA; 2,6-dimethoxymescaline) 2,3,4,5-Tetramethoxyphenethylamine (TeMPEA; TeMPEA-1; 2-methoxymescaline)

… excerpt ends here. Continue reading the full article.

Illustrations

Worked examples

Example 1 — a first encounter with Scaline

Start with the simplest possible case. Write down what Scaline 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 Scaline 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 Scaline 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 Scaline

In research: Scaline 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 Scaline 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: Scaline is common in secondary-school and first-year university syllabi. It links to neighbouring topics Alexander Shulgin, Chemical classes of psychoactive drugs, Psychedelic phenethylamines, so understanding it makes those chapters shorter.
In everyday life: Look for Scaline 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 Scaline in 20 minutes

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

Frequently asked questions

What is Scaline in simple terms?

Why does Scaline 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 Scaline?

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 Scaline.