2C-MMDA-2 (2C-2), also known as MMDPEA-2 or 6-methoxy-MDPEA, as well as 2-methoxy-4,5-methylenedioxyphenethylamine, is a

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 ...

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 ...

and

methylenedioxyphenethylamine 3,4-Methylenedioxyphenethylamine, also known as 3,4-MDPEA, MDPEA, and homopiperonylamine, is a substituted phenethylamine formed by adding a methylenedioxy group to phenethylamine. It is structurally similar to 3,4-Methylenedioxyamphetamine, MD ...

families. "The phenethylamine analog of MMDA-2 has been prepared ..The product, 2-methoxy-4,5-methylenedioxyphenethylamine hydrochloride (2C-MMDA-2 2C-2) ..There were no effects observed at up to 2.6 milligrams, but no higher trials were made. ..The 4-carbon homologue was made similarly ..to give 1-(2-methoxy-4,5-methylenedioxyphenyl)-2-aminobutane hydrochloride (4C-MMDA-2 4C-2) ..This material has never even been tasted. ..The Tweetio homologue of MMDA-2 has been tasted, however. This is 2-ethoxy-4,5-methylenedioxyamphetamine, or EMDA-2. ..At 135 milligrams, there have been reported eyes-closed visual phenomena, with intense colors. The overall duration is similar to MMDA-2 (some 10 hours) and there are reported sleep disturbances. At 185 milligrams, the feelings were intensified, there were “marvelous eyes-closed visuals (the colors were incredible), good concentration, but distinct body-tingles and rushes.” The time span was about 12 hours from start to finish, but it proved to be impossible to sleep afterwards. This homologue is thus about a third the potency of MMDA-2." Along with

lophophine Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA), is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related t ...

(2C-MMDA-1 or MMDPEA-1), it is one of the

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

s of

methoxymethylenedioxyphenethylamine Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA), is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related ...

(MMDPEA). 2C-MMDA-2 is also the phenethylamine analogue of

MMDA-2 MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the amphetamine class. It is closely related to MMDA and MDA. Alexander Shulgin was likely the first to synthesize MMDA-2. In his book ...

Use 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 ...

'' (''Phenethylamines I Have Known and Loved''),

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 ...

described testing 2C-MMDA-2 at doses of up to 2.6mg and observed no effects but did not try higher doses.

Pharmacology

The drug is a

full agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the agoni ...

of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors. Its () values were 148nM (102%) for G_q

signaling A signal is both the process and the result of transmission of data over some media accomplished by embedding some variation. Signals are important in multiple subject fields including signal processing, information theory and biology. ...

and 589nM (107%) for

β-arrestin2 Beta-arrestin-2, or β-arrestin2, also known as arrestin beta-2, is an intracellular protein that in humans is encoded by the ''ARRB2'' gene. Members of arrestin/beta-arrestin protein family are thought to participate in agonist-mediated desens ...

signaling at the serotonin 5-HT_2A receptor, 204nM (104%) at the serotonin 5-HT_2B receptor, and 9.77nM (109%) at the serotonin 5-HT_2C receptor. 2C-MMDA-2 was more potent as a serotonin 5-HT₂ receptor agonist than

mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

Chemistry

Analogues

The

NBOMe The 25-NB (25''x''-NB''x'') series, or NBOMe series, also known as the ''N''-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C (psychedelics), 2C family. The most c ...

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 ...

of 2C-MMDA-2 is

2C2-NBOMe 2C2-NBOMe, also known as 2C-MMDA-2-NBOMe or NBOMe-MMDPEA-2, is a phenethylamine derivative from the 25-NB (NBOMe) family. It is the NBOMe derivative of 2C-MMDA-2 (MMDPEA-2). It acts as a potent agonist at the serotonin 5-HT2A receptor with we ...

. It is a highly potent serotonin 5-HT₂ receptor agonist and produces the

head-twitch response The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...

, a behavioral proxy of

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 ...

effects, in rodents.

History

in tested 2C-MMDA-2 in 1963. He described these findings in his 1991 book ''

'' (''Phenethylamines I Have Known and Loved''), which is when 2C-MMDA-2 appears to have been first described in the literature. Later, 2C-MMDA-2 was assessed in terms of

serotonin receptor 5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in multiple tissues including the central and peripheral nervous systems. They mediate both ex ...

activity by

Jason Wallach Jason Wallach (born 1987) is an American pharmacologist who studies psychedelic drugs and other hallucinogens. He is an assistant professor at Saint Joseph's University's Philadelphia College of Pharmacy. In August 2020, Wallach began a partners ...

and colleagues in 2023.

References

External links

2C-MMDA-2 - Isomer Design
{{Phenethylamines 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists Methoxyphenethylamines Methylenedioxyphenethylamines