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

3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine (MDOH), also known as MDHOET, is a lesser-known psychoactive drug within the chemical class of entactogens, psychedelics, and stimulants. MDOH is closely related to MDMA (3,4-methylenedioxymethamphetamine), commonly known as ecstasy, and is part of the substituted amphetamine and substituted methylenedioxyphenethylamine classes. Despite its structural similarity to MDMA, MDOH has been studied to a much lesser extent, and its pharmacological properties, subjective effects, and potential therapeutic applications are not well-understood.

Chemistry

MDOH is a methylenedioxyphenethylamine derivative, where the methylenedioxyphenethylamine structure is a common backbone for a broad class of psychoactive compounds. The molecule consists of a phenethylamine core with a methylenedioxy bridge between the 3 and 4 positions, to which a hydroxy group is attached at the nitrogen atom, and a methyl group is attached to the nitrogen atom, making it an N-methylated derivative.

Pharmacology

The pharmacological action of MDOH is not well-documented, but it is believed to act primarily as a serotonin, dopamine, and norepinephrine releasing agent or reuptake inhibitor, similar to other compounds in its class. This action can lead to increased neurotransmitter levels in the synapse, which is thought to be responsible for its psychoactive effects. However, the presence of the hydroxy group may significantly alter its pharmacokinetics and pharmacodynamics compared to MDMA and other related compounds.

Effects

The subjective effects of MDOH are not well-documented due to its rarity and limited use in humans. However, based on its chemical similarity to MDMA, it can be speculated that MDOH may produce effects such as euphoria, increased empathy and sociability, altered sensory perception, and mild psychedelic experiences. The potential for negative side effects, including neurotoxicity, cardiovascular issues, and overheating, similar to those associated with MDMA and other stimulants, cannot be ruled out.

Therapeutic Potential

As of now, there is no known therapeutic application for MDOH. Its structural and pharmacological similarity to MDMA suggests that it could potentially be explored for use in psychotherapy, similar to ongoing research into MDMA-assisted therapy for post-traumatic stress disorder (PTSD) and other conditions. However, extensive research would be required to understand its safety, efficacy, and potential therapeutic benefits.

Legal Status

The legal status of MDOH varies by country, but it is likely to be controlled in jurisdictions where analogues of MDMA are regulated. In countries with analogue acts, such as the United States' Federal Analogue Act, MDOH could be considered illegal to manufacture, possess, or distribute for human consumption without specific regulatory approval.

See Also

• MDMA
• Psychoactive drug
• Entactogen
• Stimulant
• Psychedelic drugs