3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine

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Chemical compound related to MDMA


3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine
INN
Drug class
Routes of administration Oral
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status Uncontrolled
CAS Number 207740-24-3
PubChem 443492
DrugBank
ChemSpider 391667
KEGG


3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine (MDHMA) is a chemical compound that is structurally related to MDMA (3,4-methylenedioxy-N-methylamphetamine). It is a member of the amphetamine class of drugs and is known for its psychoactive properties.

Chemical structure and properties[edit | edit source]

MDHMA is a derivative of amphetamine, characterized by the presence of a methylenedioxy group attached to the phenyl ring and an N-hydroxy-N-methyl group attached to the alpha carbon. The chemical formula for MDHMA is C11H15NO3.

Pharmacology[edit | edit source]

MDHMA acts as a serotonin releasing agent, similar to its analog MDMA. It is believed to increase the levels of serotonin in the brain, leading to its psychoactive effects. The compound's exact mechanism of action and its effects on other neurotransmitters such as dopamine and norepinephrine are not well-documented.

Effects[edit | edit source]

The effects of MDHMA are not extensively studied, but it is presumed to have similar effects to MDMA, including euphoria, increased sociability, and enhanced sensory perception. However, due to the presence of the N-hydroxy group, its potency and duration of action may differ.

Legal status[edit | edit source]

MDHMA is not specifically listed as a controlled substance in most jurisdictions. However, it may be considered an analog of MDMA and thus subject to regulation under analog laws in certain countries.

Synthesis[edit | edit source]

The synthesis of MDHMA involves the modification of the MDMA structure by introducing an N-hydroxy group. This can be achieved through various chemical reactions, but detailed synthetic pathways are typically not disclosed in public literature due to legal and safety concerns.

Related compounds[edit | edit source]

  • MDMA
  • MDA (3,4-methylenedioxyamphetamine)
  • MDEA (3,4-methylenedioxy-N-ethylamphetamine)

See also[edit | edit source]

Related pages[edit | edit source]

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