chemistry

Naphthylaminopropane

Naphthylaminopropane 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 Naphthylaminopropane rather than just read about it. In short: Naphthylaminopropane (NAP; code name PAL-287), also known as naphthylisopropylamine (NIPA), is an experimental drug of the amphetamine and naphthylaminopropane families that was under investigation for the treatment of alcohol and stimulant addiction. Pharmacology Pharmacodynamics Activities Naphthylaminopropane is a serotonin–norepinephrine–dopamine releasing agent (SNDRA).

Key takeaways

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

Reference excerpt

Naphthylaminopropane (NAP; code name PAL-287), also known as naphthylisopropylamine (NIPA), is an experimental drug of the amphetamine and naphthylaminopropane families that was under investigation for the treatment of alcohol and stimulant addiction.

Pharmacology

Pharmacodynamics

Activities Naphthylaminopropane is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). Its EC50Tooltip half-maximal effective concentration values for induction of monoamine release are 3.4 nM for serotonin, 11.1 nM for norepinephrine, and 12.6 nM for dopamine. The drug is also an agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. Its EC50 values are 466 nM at the serotonin 5-HT2A receptor, 40 nM at the serotonin 5-HT2B receptor, and 2.3 nM at the serotonin 5-HT2C receptor. It is a full agonist of the serotonin 5-HT2A and 5-HT2B receptors and a weak partial agonist of the serotonin 5-HT2C receptor (EmaxTooltip maximal efficacy = 20%). Naphthylaminopropane has been found to act as a potent monoamine oxidase A (MAO-A) inhibitor, with an IC50Tooltip half-maximal inhibitory concentration of 420 nM. This is similar to the potency of the well-known MAO-A inhibitors para-methoxyamphetamine (PMA) and 4-methylthioamphetamine (4-MTA).

Effects In animal studies, naphthylaminopropane was shown to reduce cocaine self-administration, yet produced relatively weak stimulant effects when administered alone, being a much less effective stimulant than dextroamphetamine. Further research was being conducted in primates to see if the drug would be a useful substitute for treating drug addiction in humans. An important observation is that in behavioral studies, rodents would consistently self-administer selective norepinephrine–dopamine releasing agents (NDRAs) like dextroamphetamine, yet compounds that also potently release serotonin like naphthylaminopropane would not be self-administered. In addition to the drug's effects on self-administration, the available evidence suggests that the locomotor activation caused by dopamine releasers is also dampened when they additionally induce serotonin release. Notably, despite potent dopamine release induction, naphthylaminopropane produces weak or no locomotor activation in rodents. The high affinity of naphthylaminopropane for the serotonin 5-HT2C receptor meant that it might function as an appetite suppressant and was being considered for possible clinical use for this indication (i.e., weight loss). However, concerns were raised over the affinity of the drug for the serotonin 5-HT2B receptor, since some of the more serious side effects of the serotonin-releasing weight loss drug fenfluramine were linked to activation of this receptor. It is uncertain, although was considered unlikely per the researchers who developed the drug, that activation of the serotonin 5-HT2A and 5-HT2B receptors occurs to a significant degree in vivo.

Chemistry Naphthylaminopropane was first described in the scientific literature by 1939. The drug is also known as 2-naphthylaminopropane (2-NAP) or β-naphthylaminopropane, and it was described along with its positional isomer 1-naphthylaminopropane (1-NAP; α-naphthylaminopropane). Both 2-NAP and 1-NAP failed to substitute for dextroamphetamine in rodent drug discrimination tests, suggesting that they lack psychostimulant-like effects. The β-keto and N-methyl analogue of 2-NAP has been assessed and was found to act as a potent SNDRA similarly to naphthylaminopropane. Naphthylaminopropane is structurally related to certain rigid analogues of amphetamine. Rigid amphetamine analogues include 2-aminotetralin (2-AT), 2-amino-1,2-dihydronaphthalene (2-ADN), 1-phenylpiperazine (1-PP), 2-aminoindane (2-AI), 6-ABTooltip 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and 7-ABTooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene. A few derivatives of naphthylaminopropane have been developed or have appeared, including methamnetamine (N-methylnaphthylaminopropane; MNAP; PAL-1046), N-ethylnaphthylaminopropane (ENAP; PAL-1045), and BMAPN (βk-methamnetamine; β-keto-MNAP; 2-naphthylmethcathinone). Like naphthylaminopropane, these derivatives also act as potent monoamine releasing agents, including of serotonin, norepinephrine, and/or dopamine.

See also Substituted naphthylethylamine 5-APDI 6-APT HDEP-28 HDMP-28 Naphthylmetrazine Naphyrone Naphthylpropylaminopentane

References

Illustrations

Worked examples

Example 1 — a first encounter with Naphthylaminopropane

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

In research: Naphthylaminopropane 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 Naphthylaminopropane 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: Naphthylaminopropane is common in secondary-school and first-year university syllabi. It links to neighbouring topics 2-Naphthyl compounds, 5-HT2A agonists, 5-HT2B agonists, so understanding it makes those chapters shorter.
In everyday life: Look for Naphthylaminopropane 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 Naphthylaminopropane in 20 minutes

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

Frequently asked questions

What is Naphthylaminopropane in simple terms?

Why does Naphthylaminopropane 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 Naphthylaminopropane?

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 Naphthylaminopropane.