3,4-Methylenedioxy-N-hydroxyamphetamine

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Chemical compound


3,4-Methylenedioxy-N-hydroxyamphetamine
INN
Drug class
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number 74698-46-5
PubChem 4433
DrugBank
ChemSpider 4278
KEGG


3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH) 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.

Chemical Structure

MDOH is characterized by the presence of a methylenedioxy group attached to the phenyl ring and an N-hydroxy group attached to the amphetamine backbone. The chemical formula for MDOH is C10H13NO3.

Pharmacology

MDOH is known to act as a serotonin releasing agent, similar to its analogs MDA and MDMA. It affects the central nervous system by increasing the release of serotonin, which can lead to altered mood and perception.

Effects

The effects of MDOH are not as well-documented as those of MDMA or MDA. However, it is believed to produce entactogenic effects, which are characterized by feelings of emotional closeness and empathy. The psychoactive effects are likely to be similar to those of other empathogens.

Legal Status

The legal status of MDOH varies by country. In many jurisdictions, it is considered a controlled substance due to its structural similarity to MDMA and MDA, which are both classified as illegal drugs.

Synthesis

The synthesis of MDOH involves the introduction of an N-hydroxy group to the amphetamine structure. This can be achieved through various chemical reactions, often starting from precursor compounds such as safrole or isosafrole.

Related Compounds

See Also

Related pages

  • Structure of 3,4-Methylenedioxy-N-hydroxyamphetamine

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Contributors: Prab R. Tumpati, MD