Substituted phenethylamine: Difference between revisions

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'''Substituted phenethylamine''' is a broad class of organic compounds that share a common phenethylamine backbone. Phenethylamine itself is a simple organic compound with the formula C<sub>8</sub>H<sub>11</sub>N, consisting of a phenyl ring and an ethylamine chain. Substituted phenethylamines include a wide range of psychoactive drugs, neurotransmitters, and hormones, distinguished by the addition of various chemical groups to the basic phenethylamine structure. These modifications can significantly alter the compounds' pharmacological properties, making this class of compounds extremely diverse in terms of their effects and applications.
{{Short description|Overview of substituted phenethylamines}}


==Chemical Structure and Classification==
==Substituted Phenethylamines==
Substituted phenethylamines are characterized by the presence of different substituents at various positions on the phenethylamine skeleton. The core structure is phenyl-(CH<sub>2</sub>-CH<sub>2</sub>-NH<sub>2</sub>), and modifications can occur on the phenyl ring (at positions R<sub>1</sub> to R<sub>5</sub>), the alpha carbon (α), or the amino group (NH<sub>2</sub>).
Substituted phenethylamines are a class of compounds that are structurally related to the [[phenethylamine]] molecule. These compounds are characterized by the presence of a phenethylamine core, which consists of a phenyl ring attached to an ethylamine chain. The substitution of various functional groups on the phenyl ring or the ethylamine chain results in a wide variety of compounds with diverse pharmacological properties.


These compounds can be classified based on their substitution patterns, such as:
==Chemical Structure==
* '''Alpha-methylphenethylamine (amphetamine) derivatives''', where a methyl group is added to the alpha carbon.
The basic structure of a phenethylamine consists of a benzene ring (phenyl group) attached to a two-carbon chain ending in an amine group (ethylamine). Substitutions can occur at various positions on the benzene ring or on the ethylamine chain, leading to different chemical and pharmacological properties.
* '''Methylenedioxy derivatives''', which include compounds like MDMA (3,4-methylenedioxymethamphetamine), where a methylenedioxy group is attached to the phenyl ring.
 
* '''Halogenated derivatives''', where one or more halogen atoms (fluorine, chlorine, bromine, or iodine) are attached to the phenyl ring.
[[File:Phenethylamine_structure.png|thumb|right|200px|Basic structure of phenethylamine.]]


==Pharmacology==
==Pharmacology==
The pharmacological effects of substituted phenethylamines vary widely, ranging from stimulant and entactogenic effects to psychedelic and hallucinogenic experiences. This diversity is largely due to the differences in how these compounds interact with various neurotransmitter systems in the brain, including serotonin, dopamine, and norepinephrine pathways.
Substituted phenethylamines can act as [[neurotransmitter]]s, [[neuromodulator]]s, or [[psychoactive drug]]s. They often interact with [[monoamine]] receptors, such as [[dopamine]], [[serotonin]], and [[norepinephrine]] receptors, influencing mood, perception, and cognition.


* '''Stimulants''': Compounds like amphetamine and methamphetamine increase the release of monoamines, leading to increased alertness, concentration, and physical energy.
===Psychoactive Effects===
* '''Entactogens''': MDMA and similar compounds primarily enhance serotonin release, promoting feelings of empathy, euphoria, and emotional closeness.
Many substituted phenethylamines are known for their psychoactive effects. For example, [[amphetamine]] and its derivatives are potent central nervous system stimulants, while others like [[MDMA]] (3,4-methylenedioxy-N-methylamphetamine) are known for their empathogenic and entactogenic effects.
* '''Psychedelics''': Substances such as 2C-B and DOI affect serotonin receptors, particularly the 5-HT<sub>2A</sub> subtype, leading to altered perception, mood, and thought.


==Therapeutic Uses==
===Therapeutic Uses===
Some substituted phenethylamines have recognized medical uses. For example, amphetamines are prescribed for attention deficit hyperactivity disorder (ADHD) and narcolepsy due to their stimulant properties. MDMA is currently under research for its potential to assist in psychotherapy for post-traumatic stress disorder (PTSD).
Some substituted phenethylamines have therapeutic applications. For instance, amphetamines are used in the treatment of [[attention deficit hyperactivity disorder]] (ADHD) and [[narcolepsy]].


==Risks and Legal Status==
==Examples of Substituted Phenethylamines==
The safety profile and legal status of substituted phenethylamines vary significantly. While some, like prescription amphetamines, are controlled substances used in medicine, others, such as many novel psychoactive substances, may be unregulated or illegal. Risks associated with their use include addiction, neurotoxicity, and adverse psychological effects.


==See Also==
===Amphetamines===
Amphetamines are a well-known class of substituted phenethylamines. They include:
* [[Amphetamine]]
* [[Methamphetamine]]
* [[MDMA]]
 
===Phenethylamine Hallucinogens===
Some substituted phenethylamines are known for their hallucinogenic properties, such as:
* [[2C-B]]
* [[Mescaline]]
 
===Other Derivatives===
Other notable derivatives include:
* [[Bupropion]] - an atypical antidepressant
* [[Phenylephrine]] - a decongestant
 
==Synthesis==
The synthesis of substituted phenethylamines involves the introduction of various functional groups onto the phenethylamine core. This can be achieved through different chemical reactions, such as alkylation, acylation, or halogenation.
 
==Safety and Legal Status==
The safety and legal status of substituted phenethylamines vary widely depending on the specific compound. Some are controlled substances due to their potential for abuse and addiction, while others are legally available for medical use.
 
==Related Pages==
* [[Phenethylamine]]
* [[Phenethylamine]]
* [[Amphetamine]]
* [[Amphetamine]]
* [[MDMA]]
* [[Psychoactive drug]]
* [[Psychoactive drug]]
* [[Neurotransmitter]]
* [[Neurotransmitter]]
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[[Category:Phenethylamines]]
[[Category:Phenethylamines]]
[[Category:Psychoactive drugs]]
[[Category:Psychoactive drugs]]
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{{Pharmacology-stub}}
{{Medicine-stub}}
<gallery>
File:Phenylethyl_Amine_General_Formula_V1.svg|Substituted_phenethylamine
File:Phenethylamine2DCSD.svg|Substituted_phenethylamine
File:Meta-Tyramine.svg|Substituted_phenethylamine
File:Tyramine.svg|Substituted_phenethylamine
File:Dopamine.svg|Substituted_phenethylamine
File:Epinephrine.svg|Substituted_phenethylamine
File:Norepinephrine.svg|Substituted_phenethylamine
File:Norfenefrine.png|Substituted_phenethylamine
File:Octapamine.svg|Substituted_phenethylamine
File:6-Hydroxydopamine.svg|Substituted_phenethylamine
File:Phenylephrine_v2.svg|Substituted_phenethylamine
File:Isoprenaline.svg|Substituted_phenethylamine
</gallery>
== Substituted_phenethylamine ==
<gallery>
File:Phenylethyl_Amine_General_Formula_V1.svg|Substituted_phenethylamine
File:Phenethylamine2DCSD.svg|Substituted_phenethylamine
File:Meta-Tyramine.svg|Substituted_phenethylamine
File:Tyramine.svg|Substituted_phenethylamine
File:Dopamine.svg|Substituted_phenethylamine
File:Epinephrine.svg|Substituted_phenethylamine
File:Norepinephrine.svg|Substituted_phenethylamine
File:Norfenefrine.png|Substituted_phenethylamine
File:Octapamine.svg|Substituted_phenethylamine
File:6-Hydroxydopamine.svg|Substituted_phenethylamine
File:Phenylephrine_v2.svg|Substituted_phenethylamine
File:Isoprenaline.svg|Substituted_phenethylamine
</gallery>

Latest revision as of 17:44, 18 February 2025

Overview of substituted phenethylamines


Substituted Phenethylamines[edit]

Substituted phenethylamines are a class of compounds that are structurally related to the phenethylamine molecule. These compounds are characterized by the presence of a phenethylamine core, which consists of a phenyl ring attached to an ethylamine chain. The substitution of various functional groups on the phenyl ring or the ethylamine chain results in a wide variety of compounds with diverse pharmacological properties.

Chemical Structure[edit]

The basic structure of a phenethylamine consists of a benzene ring (phenyl group) attached to a two-carbon chain ending in an amine group (ethylamine). Substitutions can occur at various positions on the benzene ring or on the ethylamine chain, leading to different chemical and pharmacological properties.

Basic structure of phenethylamine.

Pharmacology[edit]

Substituted phenethylamines can act as neurotransmitters, neuromodulators, or psychoactive drugs. They often interact with monoamine receptors, such as dopamine, serotonin, and norepinephrine receptors, influencing mood, perception, and cognition.

Psychoactive Effects[edit]

Many substituted phenethylamines are known for their psychoactive effects. For example, amphetamine and its derivatives are potent central nervous system stimulants, while others like MDMA (3,4-methylenedioxy-N-methylamphetamine) are known for their empathogenic and entactogenic effects.

Therapeutic Uses[edit]

Some substituted phenethylamines have therapeutic applications. For instance, amphetamines are used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy.

Examples of Substituted Phenethylamines[edit]

Amphetamines[edit]

Amphetamines are a well-known class of substituted phenethylamines. They include:

Phenethylamine Hallucinogens[edit]

Some substituted phenethylamines are known for their hallucinogenic properties, such as:

Other Derivatives[edit]

Other notable derivatives include:

Synthesis[edit]

The synthesis of substituted phenethylamines involves the introduction of various functional groups onto the phenethylamine core. This can be achieved through different chemical reactions, such as alkylation, acylation, or halogenation.

Safety and Legal Status[edit]

The safety and legal status of substituted phenethylamines vary widely depending on the specific compound. Some are controlled substances due to their potential for abuse and addiction, while others are legally available for medical use.

Related Pages[edit]