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 ...
'',
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 ...
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-HT2A and
5-HT2C 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-HT2B 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
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 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
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 ...
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
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 ...
.
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.
See also
*
2,5-Dimethoxy-4-substituted amphetamines (DOx)
References
External links
MEM - Isomer DesignThe Small & Handy MEM Thread - BluelightMEM - PiHKAL - ErowidMEM - 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