chemistry

Substituted benzofuran

Substituted benzofuran 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 Substituted benzofuran rather than just read about it. In short: The substituted benzofurans are a class of chemical compounds based on the heterocyclic and polycyclic compound benzofuran. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens.

Key takeaways

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

Reference excerpt

The substituted benzofurans are a class of chemical compounds based on the heterocyclic and polycyclic compound benzofuran. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens. In general, these compounds have a benzofuran core to which a 2-aminoethyl group is attached (at any position), and combined with a range of other substituents. Some psychoactive derivatives from this family have been sold under the street name Benzofury.

Use and effects

Benzofurans like 5-APB and 6-APB are said to have relatively minor psychedelic effects.

Interactions

Pharmacology

Pharmacodynamics

Benzofurans like 5-APB and 6-APB act as serotonin–norepinephrine–dopamine releasing agents and as serotonin 5-HT2 receptor agonists. In addition, some benzofurans, including 5-MAPB, 6-MAPB, BK-5-MAPB, and BK-6-MAPB, have unexpectedly been found to be potent serotonin 5-HT1B receptor agonists. Along with serotonin release and other actions, this property may be involved may be involved in their entactogenic effects. Conversely, MDMA is much less potent as an agonist of the serotonin 5-HT1B receptor.

Chemistry

History The 2,3-dihydrobenzofurans 5-APDB and 6-APDB were described by David E. Nichols and colleagues at Purdue University as MDMA analogues in 1993. Subsequently, the benzofurans 5-APB and 6-APB emerged as novel designer drugs in 2010. Prior to this, they had been patented by Eli Lilly and Company as serotonin 5-HT2C receptor agonists for potential treatment of eating disorders and seizures in 2000 and 2006. 5-APB and 6-APB are often confused with 5-APDB and 6-APDB. The pharmacology of various benzofurans and 2,3-dihydrobenzofurans was further clarified in the mid-2010s and thereafter.

Society and culture

Legal status Substituted benzofurans saw widespread use as recreational drugs by being sold as research chemicals making them exempt from drug legislation. Many of the more common compounds were banned in the UK in June 2013 as temporary class drugs, while others have been made permanently illegal in various jurisdictions.

List of substituted benzofurans

The derivatives may be produced by substitutions at six locations of the benzofuran molecule, as well as saturation of the 2,3- double bond. The following table displays notable derivatives that have been reported:

See also Substituted methylenedioxyphenethylamine § Related compounds Substituted 2-aminoindane Substituted amphetamine Substituted benzothiophene Substituted cathinone Substituted methylenedioxyphenethylamine Substituted methoxyphenethylamine Substituted naphthylethylamine Substituted phenethylamine Substituted tryptamine Aminopropylindole

References

Illustrations

Worked examples

Example 1 — a first encounter with Substituted benzofuran

Start with the simplest possible case. Write down what Substituted benzofuran 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 Substituted benzofuran 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 Substituted benzofuran 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 Substituted benzofuran

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

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

Frequently asked questions

What is Substituted benzofuran in simple terms?

Why does Substituted benzofuran 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 Substituted benzofuran?

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 Substituted benzofuran.