Methylenedioxyhydroxyethylamphetamine

Chemical compound

Methylenedioxyhydroxyethylamphetamine
INN
Drug class
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number
PubChem
DrugBank
ChemSpider
KEGG

Methylenedioxyhydroxyethylamphetamine (MDHOET) is a chemical compound that belongs to the class of substituted amphetamines. It is structurally related to 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxymethamphetamine (MDMA), which are well-known psychoactive substances. MDHOET is characterized by the presence of a methylenedioxy group attached to the phenyl ring and an ethylamino group attached to the alpha carbon of the ethyl chain.

Chemical Structure and Properties

Chemical structure of Methylenedioxyhydroxyethylamphetamine

MDHOET is a derivative of the phenethylamine class, specifically a member of the methylenedioxyphenethylamine family. Its chemical structure includes a 1,3-benzodioxole ring, which is a methylenedioxy group attached to a benzene ring, and an ethylamino group attached to the alpha carbon of the ethyl chain. The presence of a hydroxyl group on the ethyl chain distinguishes it from other related compounds such as MDA and MDMA.

The molecular formula of MDHOET is C₁₁H₁₅NO₃, and it has a molar mass of 209.24 g/mol. The compound is typically synthesized in a laboratory setting and is not known to occur naturally.

Pharmacology

MDHOET is believed to act as a serotonin and dopamine releasing agent, similar to other substituted amphetamines. However, due to the presence of the hydroxyl group, its pharmacological profile may differ from that of MDA and MDMA. The hydroxyl group can influence the compound's ability to cross the blood-brain barrier, potentially affecting its psychoactive properties.

The exact mechanism of action of MDHOET is not well-documented, and its effects on the human body are not fully understood. It is hypothesized to interact with monoamine transporters, leading to increased levels of serotonin and dopamine in the synaptic cleft, which may result in mood enhancement and altered perception.

Legal Status

MDHOET is not widely recognized or regulated in many jurisdictions. However, due to its structural similarity to controlled substances like MDA and MDMA, it may be considered an analogue under certain analogue drug laws. This could subject it to legal restrictions similar to those of its more well-known counterparts.

Synthesis

The synthesis of MDHOET involves the reaction of 3,4-methylenedioxyphenylacetone with ethylamine, followed by reduction to introduce the hydroxyl group. The process requires careful control of reaction conditions to ensure the correct stereochemistry and purity of the final product.

Potential Uses and Research

As of now, MDHOET has not been extensively studied for medical or therapeutic applications. Its potential use as a research chemical in the study of neurotransmitter systems and psychoactive effects remains a possibility. However, due to the lack of comprehensive studies, its safety profile and potential benefits are not well-established.

Related Pages

• 3,4-Methylenedioxyamphetamine
• 3,4-Methylenedioxymethamphetamine
• Substituted amphetamines
• Serotonin releasing agent