DOx: Difference between revisions

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'''DOx''' is a chemical class of substituted amphetamine compounds that have potent psychedelic effects, including [[4-FA]]; some, like [[DOM]], have been used recreationally. The DOx family includes [[DOB]], [[DOC]], [[DOI]] and others.
{{DISPLAYTITLE:DOx}}


== History ==
==Overview==
The term DOx refers to a broad class of chemicals which include DOB, DOC, DOI and others. These compounds were first synthesized by [[Alexander Shulgin]] in the 1960s and 1970s. In his book [[PiHKAL (Phenethylamines I Have Known And Loved)]], Shulgin lists the dosage range for DOB as 1-3 mg, the duration as 18–30 hours, and the effects as "very strong, long duration, psychedelic".  
The '''DOx''' class of compounds refers to a group of [[psychedelic]] [[phenethylamines]] that are structurally related to [[2,5-dimethoxyamphetamine]] (2,5-DMA). These compounds are known for their potent [[hallucinogenic]] effects and are often used in [[psychedelic research]] and recreational settings. The DOx series includes several well-known substances such as [[DOB]], [[DOC]], and [[DOI]].


== Pharmacology ==
[[File:2,5-DMA.svg|thumb|right|Structure of 2,5-Dimethoxyamphetamine (2,5-DMA)]]
DOx compounds are often taken orally, and many have a long onset of action, often two to three hours. The effects of DOx compounds can last from 14 to 20 hours. DOx compounds are partial agonists at the [[5-HT2A receptor]] and have a high affinity for the [[5-HT2B receptor]] and the [[5-HT2C receptor]].


== Effects ==
==Chemical Structure==
The effects of DOx compounds are similar to those of other [[psychedelic drugs]]. The user may experience visual hallucinations, changes in mood, introspection, euphoria, and altered perception of time and space. At high doses or in sensitive individuals, these effects can be overwhelming and can cause panic attacks, confusion, and delirium.
The DOx compounds are characterized by the presence of a 2,5-dimethoxy substitution pattern on the phenyl ring and an alpha-methyl group on the side chain, similar to [[amphetamine]]. The "x" in DOx represents a halogen or other substituent at the 4-position of the phenyl ring, which can significantly alter the compound's potency and effects.


== Legal status ==
==Pharmacology==
The legal status of DOx compounds varies from country to country. Many countries have laws that ban the manufacture, sale, and possession of DOx compounds. In the United States, DOx compounds are classified as Schedule I controlled substances.
DOx compounds act primarily as [[serotonin receptor]] agonists, particularly at the [[5-HT2A receptor]], which is believed to be responsible for their psychedelic effects. They may also interact with other serotonin receptors and have varying degrees of activity at [[dopamine]] and [[norepinephrine]] receptors.


== See also ==
==Effects==
* [[Phenethylamine]]
The effects of DOx compounds can vary widely depending on the specific compound and dosage. Common effects include altered perception of time and space, visual and auditory hallucinations, and changes in mood and thought processes. These compounds are known for their long duration of action, often lasting 12-24 hours or more.
* [[Psychedelic drug]]
 
* [[Recreational drug use]]
==Common DOx Compounds==
 
===DOB===
[[File:DOB-racemic-skeletal.svg|thumb|left|Structure of DOB]]
'''DOB''' (2,5-dimethoxy-4-bromoamphetamine) is one of the most well-known DOx compounds. It is known for its strong psychedelic effects and long duration.
 
===DOC===
[[File:DOC-racemic-skeletal.svg|thumb|right|Structure of DOC]]
'''DOC''' (2,5-dimethoxy-4-chloroamphetamine) is another popular DOx compound, known for its intense visual effects and long-lasting experience.
 
===DOI===
'''DOI''' (2,5-dimethoxy-4-iodoamphetamine) is similar to DOB and DOC in its effects and duration, with a reputation for producing vivid visual hallucinations.
 
===Other Variants===
Other less common DOx compounds include [[DOAM]], [[DOBU]], [[MEM]], [[DOMOM]], and [[DOMOE]]. Each of these has unique properties and effects, contributing to the diversity of experiences within the DOx class.
 
[[File:DOAM.png|thumb|left|Structure of DOAM]]
[[File:DOBU.svg|thumb|right|Structure of DOBU]]
[[File:MEM.svg|thumb|left|Structure of MEM]]
[[File:DOMOM_structure.png|thumb|right|Structure of DOMOM]]
[[File:DOMOE_structure.png|thumb|left|Structure of DOMOE]]


== References ==
==Safety and Legal Status==
<references />
The safety profile of DOx compounds is not well-established, and they can pose significant risks, especially at high doses. Potential adverse effects include [[hypertension]], [[tachycardia]], [[anxiety]], and [[psychosis]]. The legal status of DOx compounds varies by country, with many being classified as controlled substances due to their potential for abuse and lack of medical use.


[[Category:Psychedelic drugs]]
==Related Pages==
[[Category:Amphetamines]]
* [[Psychedelic drug]]
[[Category:Phenethylamines]]
* [[Phenethylamine]]
* [[Serotonin receptor]]
* [[Hallucinogen]]


{{stub}}
[[Category:Psychedelic phenethylamines]]
==DOx==
[[Category:Serotonin receptor agonists]]
<gallery>
File:2,5-DMA.svg|DOx
File:2,5-DMA.svg|DOx
File:DOAM.png|DOx
File:DOB-racemic-skeletal.svg|DOx
File:DOBU.svg|DOx
File:DOC-racemic-skeletal.svg|DOx
File:MEM.svg|DOx
File:DOMOM_structure.png|DOx
File:DOMOE_structure.png|DOx
File:2,5-Dimethoxy-4-ethylamphetamine.svg|DOx
File:2,5-dimethoxy-4-ethylthioamphetamine.svg|DOx
File:2,5-Dimethoxy-4-fluoroamphetamine.svg|DOx
</gallery>
<gallery>
File:2,5-DMA.svg|DOx
File:2,5-DMA.svg|DOx
File:DOAM.png|DOx
File:DOB-racemic-skeletal.svg|DOx
File:DOBU.svg|DOx
File:DOC-racemic-skeletal.svg|DOx
File:MEM.svg|DOx
File:DOMOM_structure.png|DOx
File:DOMOE_structure.png|DOx
File:2,5-Dimethoxy-4-ethylamphetamine.svg|DOx
File:2,5-dimethoxy-4-ethylthioamphetamine.svg|DOx
File:2,5-Dimethoxy-4-fluoroamphetamine.svg|DOx
</gallery>

Latest revision as of 11:02, 23 March 2025


Overview[edit]

The DOx class of compounds refers to a group of psychedelic phenethylamines that are structurally related to 2,5-dimethoxyamphetamine (2,5-DMA). These compounds are known for their potent hallucinogenic effects and are often used in psychedelic research and recreational settings. The DOx series includes several well-known substances such as DOB, DOC, and DOI.

Structure of 2,5-Dimethoxyamphetamine (2,5-DMA)

Chemical Structure[edit]

The DOx compounds are characterized by the presence of a 2,5-dimethoxy substitution pattern on the phenyl ring and an alpha-methyl group on the side chain, similar to amphetamine. The "x" in DOx represents a halogen or other substituent at the 4-position of the phenyl ring, which can significantly alter the compound's potency and effects.

Pharmacology[edit]

DOx compounds act primarily as serotonin receptor agonists, particularly at the 5-HT2A receptor, which is believed to be responsible for their psychedelic effects. They may also interact with other serotonin receptors and have varying degrees of activity at dopamine and norepinephrine receptors.

Effects[edit]

The effects of DOx compounds can vary widely depending on the specific compound and dosage. Common effects include altered perception of time and space, visual and auditory hallucinations, and changes in mood and thought processes. These compounds are known for their long duration of action, often lasting 12-24 hours or more.

Common DOx Compounds[edit]

DOB[edit]

Structure of DOB

DOB (2,5-dimethoxy-4-bromoamphetamine) is one of the most well-known DOx compounds. It is known for its strong psychedelic effects and long duration.

DOC[edit]

Structure of DOC

DOC (2,5-dimethoxy-4-chloroamphetamine) is another popular DOx compound, known for its intense visual effects and long-lasting experience.

DOI[edit]

DOI (2,5-dimethoxy-4-iodoamphetamine) is similar to DOB and DOC in its effects and duration, with a reputation for producing vivid visual hallucinations.

Other Variants[edit]

Other less common DOx compounds include DOAM, DOBU, MEM, DOMOM, and DOMOE. Each of these has unique properties and effects, contributing to the diversity of experiences within the DOx class.

Structure of DOAM
Structure of DOBU
Structure of MEM
Structure of DOMOM
Structure of DOMOE

Safety and Legal Status[edit]

The safety profile of DOx compounds is not well-established, and they can pose significant risks, especially at high doses. Potential adverse effects include hypertension, tachycardia, anxiety, and psychosis. The legal status of DOx compounds varies by country, with many being classified as controlled substances due to their potential for abuse and lack of medical use.

Related Pages[edit]