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{{Short description|Chemical compound}}
{{Drugbox
| verifiedfields = changed
| verifiedrevid = 477318123
| IUPAC_name = 1-(4-Hydroxy-3-methoxyphenyl)propan-2-amine
| image = 4-Hydroxy-3-methoxyamphetamine.svg
| image_size = 200px
| image_alt = Structural formula of 4-Hydroxy-3-methoxyamphetamine
| width =
| alt =
| caption = Chemical structure of 4-Hydroxy-3-methoxyamphetamine
| CAS_number = 64116-12-5
| PubChem = 443680
| ChemSpiderID = 391837
| UNII = 0F3X4QZV3R
| ChEMBL = 127631
| C=10
| H=15
| N=1
| O=2
| smiles = CC(CC1=CC(=C(C=C1)O)OC)N
| InChI = 1S/C10H15NO2/c1-7(11)4-8-3-5-9(12)10(6-8)13-2/h3,5-7,12H,4,11H2,1-2H3
| InChIKey = YXJYVOSKFXYQEQ-UHFFFAOYSA-N
}}

'''4-Hydroxy-3-methoxyamphetamine''' ('''HMA''') is a [[psychoactive drug]] and a member of the [[amphetamine]] class of [[phenethylamine]]s. It is a [[metabolite]] of the [[psychedelic]] drug [[mescaline]] and is structurally related to other [[substituted amphetamines]].

==Chemical Structure and Properties==
[[File:4-Hydroxy-3-methoxyamphetamine.svg|Chemical structure of 4-Hydroxy-3-methoxyamphetamine|thumb|right]]
4-Hydroxy-3-methoxyamphetamine is characterized by the presence of a [[hydroxy group]] at the 4-position and a [[methoxy group]] at the 3-position on the [[phenyl ring]]. The compound has the molecular formula C10H15NO2 and a molecular weight of 181.23 g/mol. The presence of these functional groups contributes to its pharmacological activity and its interaction with [[neurotransmitter]] systems in the brain.

==Pharmacology==
4-Hydroxy-3-methoxyamphetamine acts primarily as a [[serotonin]] and [[dopamine]] releasing agent. It is thought to exert its effects by increasing the levels of these neurotransmitters in the [[synaptic cleft]], leading to enhanced neurotransmission. This mechanism is similar to that of other [[psychedelic]] and [[stimulant]] drugs, which can result in altered [[perception]], mood, and cognition.

==Metabolism==
As a metabolite of [[mescaline]], 4-Hydroxy-3-methoxyamphetamine is formed in the body following the ingestion of mescaline. The metabolic pathway involves the [[demethylation]] of mescaline, followed by further enzymatic transformations. The presence of this metabolite in the body can be indicative of mescaline use and is often studied in the context of [[drug metabolism]] and [[pharmacokinetics]].

==Potential Effects and Uses==
While 4-Hydroxy-3-methoxyamphetamine itself is not commonly used as a recreational drug, its role as a metabolite of mescaline makes it of interest in the study of [[psychedelic]] substances. The compound's effects are likely to be similar to those of mescaline, including [[hallucinogenic]] experiences, altered [[sensory perception]], and changes in [[thought processes]].

==Safety and Legal Status==
The safety profile of 4-Hydroxy-3-methoxyamphetamine is not well-documented, as it is primarily studied in the context of its parent compound, mescaline. The legal status of this compound varies by jurisdiction, but it is generally controlled under laws regulating [[psychoactive substances]].

==Related Compounds==
4-Hydroxy-3-methoxyamphetamine is related to other [[substituted amphetamines]] such as [[3,4-methylenedioxyamphetamine]] (MDA) and [[3,4-methylenedioxymethamphetamine]] (MDMA). These compounds share similar structural features and pharmacological properties, contributing to their classification within the same chemical family.

==Related Pages==
* [[Mescaline]]
* [[Amphetamine]]
* [[Psychedelic drug]]
* [[Neurotransmitter]]

[[Category:Amphetamines]]
[[Category:Psychedelic phenethylamines]]
[[Category:Serotonin releasing agents]]

4-Hydroxy-3-methoxyamphetamine - Revision history

Prab: CSV import