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 5-HT2 receptor agonist of the phenethylamine and methylenedioxyphenethylamine 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 (2C-MMDA-1 or MMDPEA-1), it is one of the positional isomers of methoxymethylenedioxyphenethylamine (MMDPEA). 2C-MMDA-2 is also the phenethylamine analogue of MMDA-2.
Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin described testing 2C-MMDA-2 at doses of up to 2.6mg and observed no effects but did not try higher doses.
Pharmacology Pharmacodynamics 2C-MMDA-2 is a full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. Its () values were 148nM (102%) for Gq signaling and 589nM (107%) for β-arrestin2 signaling at the serotonin 5-HT2A receptor, 204nM (104%) at the serotonin 5-HT2B receptor, and 9.77nM (109%) at the serotonin 5-HT2C receptor. 2C-MMDA-2 was more potent as a serotonin 5-HT2 receptor agonist than mescaline.
Chemistry Analogues The NBOMe derivative of 2C-MMDA-2 is 2C2-NBOMe. It is a highly potent serotonin 5-HT2 receptor agonist and produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.
History Alexander Shulgin in tested 2C-MMDA-2 in 1963. He described these findings in his 1991 book PiHKAL (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 activity by Jason Wallach and colleagues in 2023.
See also Substituted methylenedioxyphenethylamine Substituted methoxyphenethylamine Methoxymethylenedioxyphenethylamine Lophophine (2C-MMDA-1 or MMDPEA-1) 2C-MMDA-3a (MMDPEA-3a) 2C2-NBOMe (2C-MMDA-2-NBOMe)
References
External links 2C-MMDA-2 - Isomer Design