4-Hydroxy-3-methoxyamphetamine

Chemical compound

4-Hydroxy-3-methoxyamphetamine
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CAS Number	64116-12-5
PubChem	443680
DrugBank
ChemSpider	391837
KEGG

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

Chemical Structure and Properties

Chemical structure of 4-Hydroxy-3-methoxyamphetamine

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