2,5-Dimethoxy-4-ethoxyamphetamine (MEM) is a psychedelic

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

, and DOx families. It was first described by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

by 1968.

Dosage and effects

In his book ''

PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

'',

lists the active dose range of MEM as 20 to 50mg orally and the duration as 10 to 14hours. According to Shulgin, MEM produces color enhancement, visual phenomena, and pattern movement, among other effects.

Pharmacology

MEM is a

serotonergic psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

and acts as a selective

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT₂ receptor

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

. It is specifically a full agonist of the serotonin 5-HT_2A and 5-HT_2C receptors and to a lesser extent is a

partial Partial may refer to: Mathematics *Partial derivative, derivative with respect to one of several variables of a function, with the other variables held constant ** ∂, a symbol that can denote a partial derivative, sometimes pronounced "partial d ...

to full agonist of the serotonin 5-HT_2B receptor. The psychedelic effects of MEM are thought to be mediated by serotonin 5-HT_2A receptor activation.

Chemistry

MEM, also known as 2,5-dimethoxy-4-ethoxyamphetamine, is a

, and DOx

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

. It is the analogue and derivative of 2,4,5-trimethoxyamphetamine (TMA) in which a 4- ethoxy group is present instead of a 4-

methoxy group In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

Derivatives

A variety of

s of MEM have been developed and studied, for instance by Daniel Trachsel and colleagues. These include MPM, MIPM, MALM, MMALM, MFEM, MDFEM, and MTFEM, among others.

History

MEM was first synthesized by

. It was first described by him in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

by 1968.

References

External links

MEM - Isomer Design

The Small & Handy MEM Thread - Bluelight

MEM - PiHKAL - Erowid

MEM - PiHKAL - Isomer Design
{{DEFAULTSORT:Dimethoxy-4-ethoxyamphetamine, 2,5- 2,5-Dimethoxyphenethylamines 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists DOx (psychedelics) Ethoxy compounds Psychedelic phenethylamines