Substituted methylenedioxyphenethylamine: Difference between revisions

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'''Substituted methylenedioxyphenethylamine''' ('''MDxx''') is a large chemical class of [[organic compounds]] that includes many psychoactive drugs. These compounds are characterized by a phenethylamine backbone with a methylenedioxy functional group attached to the aromatic ring.
==Substituted Methylenedioxyphenethylamine==


== History ==
[[File:Methylenedioxyphenethylamine.svg|thumb|right|Substituted methylenedioxyphenethylamine]]


The first synthetic compound of this class, [[MDA (drug)|MDA]], was synthesized in 1910 by G. Mannish and W. Jacobson. However, its psychoactive effects were not discovered until the mid-20th century. The most well-known compound of this class, [[MDMA]], was first synthesized in 1912 by Merck but its psychoactive properties were not widely recognized until the 1970s.
Substituted methylenedioxyphenethylamines are a class of chemical compounds that are structurally related to the parent compound methylenedioxyphenethylamine (MDPEA). These compounds are characterized by the presence of a methylenedioxy group attached to a phenethylamine backbone. They are known for their psychoactive properties and are often used in research and recreational contexts.


== Chemistry ==
==Chemical Structure==


Substituted methylenedioxyphenethylamines are derived from [[phenethylamine]] by adding a methylenedioxy group (-O-CH2-O-) to the benzene ring. This group significantly alters the pharmacological properties of the compound. The methylenedioxy group makes the compound more lipophilic, allowing it to cross the [[blood-brain barrier]] more easily.
The basic structure of substituted methylenedioxyphenethylamines consists of a phenethylamine core with a methylenedioxy bridge attached to the benzene ring. This bridge is typically located at the 3,4-positions of the phenyl ring, although other positions are possible.


== Pharmacology ==
[[File:Methylenedioxymethylphenethylamine.svg|thumb|left|Substituted methylenedioxyphenethylamine]]


The pharmacological effects of MDxx compounds are primarily due to their action as [[serotonin]] releasing agents. They increase the release of serotonin in the brain, leading to mood elevation and feelings of empathy. Some compounds in this class, such as [[MDMA]], also have activity at other neurotransmitter systems, including the [[dopamine]] and [[norepinephrine]] systems.
The general formula for these compounds can be represented as C₆H₄O₂CH₂CH₂NH₂, with various substitutions possible on the phenyl ring, the ethyl chain, or the amine group.


== Use and effects ==
==Pharmacology==


MDxx compounds are often used recreationally for their euphoric and empathogenic effects. They are commonly associated with the [[rave]] and [[electronic dance music]] cultures. The effects of these drugs can include feelings of love, altered perception, and increased energy. However, they can also cause negative effects such as anxiety, paranoia, and neurotoxicity.
Substituted methylenedioxyphenethylamines are known for their ability to act on the central nervous system. They primarily function as [[serotonin]] and [[dopamine]] releasing agents, which contributes to their psychoactive effects. These compounds can induce effects such as euphoria, altered perception, and increased energy.


== Legal status ==
==Common Compounds==


Many MDxx compounds are controlled substances in many countries due to their potential for abuse and harm. In the United States, most are classified as [[Schedule I drugs]] under the [[Controlled Substances Act]].
Several well-known psychoactive substances belong to the substituted methylenedioxyphenethylamine class:


== See also ==
* [[3,4-Methylenedioxyamphetamine]] (MDA)
* [[3,4-Methylenedioxymethamphetamine]] (MDMA)
* [[3,4-Methylenedioxy-N-ethylamphetamine]] (MDEA)
 
[[File:BNDM-MDPEA_structure.png|thumb|right|Substituted methylenedioxyphenethylamine]]
 
These compounds are often used recreationally for their empathogenic and entactogenic effects.
 
==Synthesis==
 
The synthesis of substituted methylenedioxyphenethylamines typically involves the reaction of a methylenedioxybenzene derivative with a suitable amine precursor. Various synthetic routes can be employed, depending on the specific substitutions desired on the phenethylamine backbone.
 
==Legal Status==
 
The legal status of substituted methylenedioxyphenethylamines varies by country. Many of these compounds are controlled substances due to their potential for abuse and psychoactive effects. For example, MDMA is classified as a Schedule I substance in the United States, indicating a high potential for abuse and no accepted medical use.
 
==Related Pages==


* [[Phenethylamine]]
* [[Phenethylamine]]
* [[Amphetamine]]
* [[Amphetamine]]
* [[Psychedelic drug]]
* [[Psychedelic drug]]
* [[Designer drug]]
* [[Entactogen]]
 
[[File:Lophophine.png|thumb|left|Substituted methylenedioxyphenethylamine]]
 
==See Also==
 
* [[Serotonin releasing agent]]
* [[Dopamine releasing agent]]
* [[Psychoactive drug]]


[[Category:Phenethylamines]]
[[Category:Psychoactive drugs]]
[[Category:Psychoactive drugs]]
[[Category:Phenethylamines]]
[[Category:Serotonin releasing agents]]
[[Category:Serotonin releasing agents]]
{{Psychoactive drug-stub}}
{{Phenethylamine-stub}}
<gallery>
File:Methylenedioxyphenethylamine.svg|Substituted_methylenedioxyphenethylamine
File:Methylenedioxyphenethylamine.svg|Substituted_methylenedioxyphenethylamine
File:Methylenedioxymethylphenethylamine.svg|Substituted_methylenedioxyphenethylamine
File:BNDM-MDPEA_structure.png|Substituted_methylenedioxyphenethylamine
File:Lophophine.png|Substituted_methylenedioxyphenethylamine
File:MMDMPEA_structure.png|Substituted_methylenedioxyphenethylamine
File:MDPEA-NBOMe_structure.png|Substituted_methylenedioxyphenethylamine
File:MDA-2D-skeletal.svg|Substituted_methylenedioxyphenethylamine
File:2,3-MDA.svg|Substituted_methylenedioxyphenethylamine
File:2,3-MDMA.svg|Substituted_methylenedioxyphenethylamine
File:MDMA_(simple).svg|Substituted_methylenedioxyphenethylamine
File:MDEA.svg|Substituted_methylenedioxyphenethylamine
</gallery>

Latest revision as of 11:17, 23 March 2025

Substituted Methylenedioxyphenethylamine[edit]

Substituted methylenedioxyphenethylamine

Substituted methylenedioxyphenethylamines are a class of chemical compounds that are structurally related to the parent compound methylenedioxyphenethylamine (MDPEA). These compounds are characterized by the presence of a methylenedioxy group attached to a phenethylamine backbone. They are known for their psychoactive properties and are often used in research and recreational contexts.

Chemical Structure[edit]

The basic structure of substituted methylenedioxyphenethylamines consists of a phenethylamine core with a methylenedioxy bridge attached to the benzene ring. This bridge is typically located at the 3,4-positions of the phenyl ring, although other positions are possible.

Substituted methylenedioxyphenethylamine

The general formula for these compounds can be represented as C₆H₄O₂CH₂CH₂NH₂, with various substitutions possible on the phenyl ring, the ethyl chain, or the amine group.

Pharmacology[edit]

Substituted methylenedioxyphenethylamines are known for their ability to act on the central nervous system. They primarily function as serotonin and dopamine releasing agents, which contributes to their psychoactive effects. These compounds can induce effects such as euphoria, altered perception, and increased energy.

Common Compounds[edit]

Several well-known psychoactive substances belong to the substituted methylenedioxyphenethylamine class:

Substituted methylenedioxyphenethylamine

These compounds are often used recreationally for their empathogenic and entactogenic effects.

Synthesis[edit]

The synthesis of substituted methylenedioxyphenethylamines typically involves the reaction of a methylenedioxybenzene derivative with a suitable amine precursor. Various synthetic routes can be employed, depending on the specific substitutions desired on the phenethylamine backbone.

Legal Status[edit]

The legal status of substituted methylenedioxyphenethylamines varies by country. Many of these compounds are controlled substances due to their potential for abuse and psychoactive effects. For example, MDMA is classified as a Schedule I substance in the United States, indicating a high potential for abuse and no accepted medical use.

Related Pages[edit]

Substituted methylenedioxyphenethylamine

See Also[edit]