3,4-Methylenedioxy-N-methoxyamphetamine

Chemical compound

3,4-Methylenedioxy-N-methoxyamphetamine
INN
Drug class
Routes of administration	Oral
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status	Uncontrolled
CAS Number	74698-46-5
PubChem	443978
DrugBank
ChemSpider	392063
KEGG

3,4-Methylenedioxy-N-methoxyamphetamine (MDMEO) is a psychedelic and empathogen of the amphetamine class. It is a derivative of 3,4-methylenedioxyamphetamine (MDA) and is structurally related to MDMA.

Chemical structure

MDMEO is a member of the substituted amphetamines class, which are characterized by the presence of a phenethylamine core with a methylenedioxy group attached to the benzene ring. The chemical structure of MDMEO includes a methoxy group attached to the nitrogen atom, distinguishing it from other related compounds such as MDA and MDMA.

Pharmacology

MDMEO is believed to act as a serotonin releasing agent, similar to other compounds in the MDxx series. It may also have effects on dopamine and norepinephrine release, contributing to its psychoactive properties. The exact mechanism of action and the receptor binding profile of MDMEO have not been extensively studied.

Effects

The effects of MDMEO are not well-documented, but it is presumed to produce effects similar to those of other entactogens and psychedelics. Users may experience altered perception, enhanced empathy, and increased sociability. The duration and intensity of these effects can vary depending on the dose and individual differences.

Legal status

MDMEO is not specifically listed as a controlled substance in most jurisdictions. However, it may be considered an analogue of controlled substances such as MDA or MDMA, which could subject it to regulation under analogue laws.

Synthesis

The synthesis of MDMEO involves the reaction of 3,4-methylenedioxyphenylacetone with methoxyamine to form the corresponding oxime, followed by reduction to the amine. This process requires specialized knowledge in organic chemistry and access to precursor chemicals.

Related compounds

• 3,4-Methylenedioxyamphetamine (MDA)
• 3,4-Methylenedioxymethamphetamine (MDMA)
• 3,4-Methylenedioxy-N-ethylamphetamine (MDEA)
• 3,4-Methylenedioxy-N-methylcathinone (Methylone)

Related pages

• Psychedelic drug
• Empathogen
• Substituted amphetamines
• Serotonin releasing agent