Substituted phenylmorpholine: Difference between revisions

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'''Substituted phenylmorpholine''' (also known as '''phenmetrazine analogues''') are a chemical class of psychoactive compounds that are based on the phenmetrazine structure. The phenmetrazine structure consists of a [[phenyl ring]] bound to a [[morpholine]] ring at the R2 position.
==Substituted Phenylmorpholine==


== History ==
[[File:Phenmetrazine_derivatives.svg|thumb|right|Substituted phenylmorpholine]]


Phenmetrazine was originally synthesized in the 1950s and was used as an [[appetite suppressant]] in the treatment of [[obesity]]. However, due to its potential for misuse and addiction, it was withdrawn from the market. This led to the development of various substituted phenylmorpholines, which are designed to mimic the effects of phenmetrazine while reducing its potential for abuse.
Substituted phenylmorpholines are a class of chemical compounds that are structurally related to [[phenylmorpholine]]. These compounds are characterized by the presence of a phenyl group attached to a morpholine ring, which is a six-membered ring containing both nitrogen and oxygen atoms. The substitution of different functional groups on the phenyl ring or the morpholine ring can lead to a variety of compounds with diverse pharmacological properties.


== Structure and Activity ==
==Chemical Structure==


The structure of substituted phenylmorpholines consists of a phenyl ring bound to a morpholine ring. The morpholine ring is a six-membered ring with one oxygen atom and one nitrogen atom. The phenyl ring is a six-membered carbon ring with five hydrogen atoms and one phenyl group. The position and type of substitution on the phenyl ring can greatly influence the activity of the compound.
[[File:2-phenylmorpholine.svg|thumb|left|2-Phenylmorpholine]]


== Pharmacology ==
The basic structure of a phenylmorpholine consists of a morpholine ring, which is a heterocyclic amine, bonded to a phenyl group. The morpholine ring itself is composed of four carbon atoms, one nitrogen atom, and one oxygen atom. Substituted phenylmorpholines can have various substituents on the phenyl ring or the morpholine ring, which can significantly alter their chemical and pharmacological properties.


Substituted phenylmorpholines act as [[stimulants]] by increasing the levels of certain chemicals in the brain. They are thought to work by inhibiting the reuptake of [[dopamine]], [[norepinephrine]], and [[serotonin]], thereby increasing the levels of these neurotransmitters in the brain. This results in increased alertness, energy, and mood elevation.
==Pharmacological Properties==


== Examples ==
Substituted phenylmorpholines are known for their stimulant and anorectic effects. They act primarily as central nervous system stimulants and have been used in the treatment of conditions such as obesity and attention deficit hyperactivity disorder (ADHD). The pharmacological activity of these compounds is largely due to their ability to increase the release of monoamines such as dopamine and norepinephrine in the brain.


Some examples of substituted phenylmorpholines include:
==Examples of Substituted Phenylmorpholines==


* [[3-Fluorophenmetrazine]] (3-FPM) - A stimulant drug that is a derivative of phenmetrazine.
===Phenmetrazine===
* [[4-Methylphenmetrazine]] (4-MPM) - A stimulant drug that is a derivative of phenmetrazine.
* [[Desoxypipradrol]] (2-DPMP) - A potent psychostimulant that is structurally related to phenmetrazine.


== Legal Status ==
[[File:Phenmetrazine.svg|thumb|right|Phenmetrazine]]


The legal status of substituted phenylmorpholines varies by country. In some countries, they are classified as controlled substances, while in others they are legal to possess and use.
Phenmetrazine is a well-known substituted phenylmorpholine that was previously used as an appetite suppressant. It was marketed under the brand name Preludin and was known for its efficacy in weight loss. However, due to its potential for abuse and addiction, it has been withdrawn from the market in many countries.


== See Also ==
===Phendimetrazine===


* [[Phenethylamine]]
[[File:Phendimetrazine.svg|thumb|left|Phendimetrazine]]
* [[Amphetamine]]
* [[Methamphetamine]]


[[Category:Psychoactive drugs]]
Phendimetrazine is another substituted phenylmorpholine that is used as an appetite suppressant. It is a prodrug that is metabolized into phenmetrazine in the body. Phendimetrazine is still available by prescription for the short-term management of obesity.
 
===Pseudophenmetrazine===
 
[[File:Pseudophenmetrazine.svg|thumb|right|Pseudophenmetrazine]]
 
Pseudophenmetrazine is a stereoisomer of phenmetrazine. It has similar pharmacological effects but is less commonly used in clinical practice.
 
===Isophenmetrazine===
 
[[File:Isophenmetrazine_structure.png|thumb|left|Isophenmetrazine]]
 
Isophenmetrazine is another derivative of phenmetrazine. It has been studied for its potential stimulant effects but is not widely used.
 
===Phenetrazine===
 
[[File:Phenetrazine_structure.png|thumb|right|Phenetrazine]]
 
Phenetrazine is a lesser-known substituted phenylmorpholine with stimulant properties. It has been investigated for its potential use in various therapeutic applications.
 
==Stereochemistry==
 
[[File:(2S,3S)-3,4-dimethyl-2-phenylmorpholine.png|thumb|left|(2S,3S)-3,4-dimethyl-2-phenylmorpholine]]
 
The stereochemistry of substituted phenylmorpholines can play a significant role in their pharmacological activity. Different stereoisomers can have varying effects on the central nervous system, and the specific configuration of the substituents can influence the compound's potency and efficacy.
 
==Related Pages==
* [[Phenylmorpholine]]
* [[Central nervous system stimulant]]
* [[Anorectic]]
* [[Monoamine]]
 
{{Portal|Chemistry}}
{{Portal|Medicine}}
 
[[Category:Phenylmorpholines]]
[[Category:Stimulants]]
[[Category:Stimulants]]
[[Category:Phenmetrazines]]
[[Category:Anorectics]]
{{Psychoactive drug-stub}}
== Substituted_phenylmorpholine ==
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File:Phenmetrazine_derivatives.svg|Substituted_phenylmorpholine
File:(2S,3S)-3,4-dimethyl-2-phenylmorpholine.png|Substituted_phenylmorpholine
File:Pseudophenmetrazine.svg|Substituted_phenylmorpholine
File:2-phenylmorpholine.svg|Substituted_phenylmorpholine
File:Phenmetrazine.svg|Substituted_phenylmorpholine
File:Phendimetrazine.svg|Substituted_phenylmorpholine
File:Isophenmetrazine_structure.png|Substituted_phenylmorpholine
File:Phenetrazine_structure.png|Substituted_phenylmorpholine
File:Phenmetetrazine_structure.png|Substituted_phenylmorpholine
File:2-phenyl-3,5-dimethylmorpholine.png|Substituted_phenylmorpholine
File:2-Phenyl-3,6-dimethylmorpholine.svg|Substituted_phenylmorpholine
File:G-130_structure.png|Substituted_phenylmorpholine
</gallery>
<gallery>
File:Phenmetrazine_derivatives.svg|Substituted_phenylmorpholine
File:(2S,3S)-3,4-dimethyl-2-phenylmorpholine.png|Substituted_phenylmorpholine
File:Pseudophenmetrazine.svg|Substituted_phenylmorpholine
File:2-phenylmorpholine.svg|Substituted_phenylmorpholine
File:Phenmetrazine.svg|Substituted_phenylmorpholine
File:Phendimetrazine.svg|Substituted_phenylmorpholine
File:Isophenmetrazine_structure.png|Substituted_phenylmorpholine
File:Phenetrazine_structure.png|Substituted_phenylmorpholine
File:Phenmetetrazine_structure.png|Substituted_phenylmorpholine
File:2-phenyl-3,5-dimethylmorpholine.png|Substituted_phenylmorpholine
File:2-Phenyl-3,6-dimethylmorpholine.svg|Substituted_phenylmorpholine
File:G-130_structure.png|Substituted_phenylmorpholine
</gallery>

Latest revision as of 18:59, 23 March 2025

Substituted Phenylmorpholine[edit]

Substituted phenylmorpholine

Substituted phenylmorpholines are a class of chemical compounds that are structurally related to phenylmorpholine. These compounds are characterized by the presence of a phenyl group attached to a morpholine ring, which is a six-membered ring containing both nitrogen and oxygen atoms. The substitution of different functional groups on the phenyl ring or the morpholine ring can lead to a variety of compounds with diverse pharmacological properties.

Chemical Structure[edit]

2-Phenylmorpholine

The basic structure of a phenylmorpholine consists of a morpholine ring, which is a heterocyclic amine, bonded to a phenyl group. The morpholine ring itself is composed of four carbon atoms, one nitrogen atom, and one oxygen atom. Substituted phenylmorpholines can have various substituents on the phenyl ring or the morpholine ring, which can significantly alter their chemical and pharmacological properties.

Pharmacological Properties[edit]

Substituted phenylmorpholines are known for their stimulant and anorectic effects. They act primarily as central nervous system stimulants and have been used in the treatment of conditions such as obesity and attention deficit hyperactivity disorder (ADHD). The pharmacological activity of these compounds is largely due to their ability to increase the release of monoamines such as dopamine and norepinephrine in the brain.

Examples of Substituted Phenylmorpholines[edit]

Phenmetrazine[edit]

Phenmetrazine

Phenmetrazine is a well-known substituted phenylmorpholine that was previously used as an appetite suppressant. It was marketed under the brand name Preludin and was known for its efficacy in weight loss. However, due to its potential for abuse and addiction, it has been withdrawn from the market in many countries.

Phendimetrazine[edit]

Phendimetrazine

Phendimetrazine is another substituted phenylmorpholine that is used as an appetite suppressant. It is a prodrug that is metabolized into phenmetrazine in the body. Phendimetrazine is still available by prescription for the short-term management of obesity.

Pseudophenmetrazine[edit]

Pseudophenmetrazine

Pseudophenmetrazine is a stereoisomer of phenmetrazine. It has similar pharmacological effects but is less commonly used in clinical practice.

Isophenmetrazine[edit]

Isophenmetrazine

Isophenmetrazine is another derivative of phenmetrazine. It has been studied for its potential stimulant effects but is not widely used.

Phenetrazine[edit]

Phenetrazine

Phenetrazine is a lesser-known substituted phenylmorpholine with stimulant properties. It has been investigated for its potential use in various therapeutic applications.

Stereochemistry[edit]

(2S,3S)-3,4-dimethyl-2-phenylmorpholine

The stereochemistry of substituted phenylmorpholines can play a significant role in their pharmacological activity. Different stereoisomers can have varying effects on the central nervous system, and the specific configuration of the substituents can influence the compound's potency and efficacy.

Related Pages[edit]

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