Substituted methylenedioxyphenethylamine

Substituted methylenedioxyphenethylamine (MDxx) is a large chemical class of organic compounds that includes many psychoactive drugs. These compounds are characterized by a phenethylamine backbone with a methylenedioxy functional group attached to the aromatic ring.

History

The first synthetic compound of this class, MDA, was synthesized in 1910 by G. Mannish and W. Jacobson. However, its psychoactive effects were not discovered until the mid-20th century. The most well-known compound of this class, MDMA, was first synthesized in 1912 by Merck but its psychoactive properties were not widely recognized until the 1970s.

Chemistry

Substituted methylenedioxyphenethylamines are derived from phenethylamine by adding a methylenedioxy group (-O-CH2-O-) to the benzene ring. This group significantly alters the pharmacological properties of the compound. The methylenedioxy group makes the compound more lipophilic, allowing it to cross the blood-brain barrier more easily.

Pharmacology

The pharmacological effects of MDxx compounds are primarily due to their action as serotonin releasing agents. They increase the release of serotonin in the brain, leading to mood elevation and feelings of empathy. Some compounds in this class, such as MDMA, also have activity at other neurotransmitter systems, including the dopamine and norepinephrine systems.

Use and effects

MDxx compounds are often used recreationally for their euphoric and empathogenic effects. They are commonly associated with the rave and electronic dance music cultures. The effects of these drugs can include feelings of love, altered perception, and increased energy. However, they can also cause negative effects such as anxiety, paranoia, and neurotoxicity.

Legal status

Many MDxx compounds are controlled substances in many countries due to their potential for abuse and harm. In the United States, most are classified as Schedule I drugs under the Controlled Substances Act.

See also

• Phenethylamine
• Amphetamine
• Psychedelic drug
• Designer drug