2C-MMDA-2

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'''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|5-HT₂ receptor]] [[agonist]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted methylenedioxyphenethylamine|methylenedioxyphenethylamine]] families.<ref name="PiHKAL">{{CitePiHKAL}} "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."</ref><ref name="ShulginManningDaley2011">{{cite book | vauthors = Shulgin A, Manning T, Daley PF | pages = 339, 347 | title = [[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]] | publisher = Transform Press | location = Berkeley, CA | volume = 1 | year = 2011 | isbn = 978-0-9630096-3-0 | oclc = 709667010}}</ref><ref name="WallachCaoCalkins2023">{{cite journal | vauthors = Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | pages = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | url = https://bitnest.netfirms.com/external/10.1038/s41467-023-44016-1}}</ref> Along with [[lophophine]] (2C-MMDA-1 or MMDPEA-1), it is one of the [[positional isomer]]s of [[methoxymethylenedioxyphenethylamine]] (MMDPEA).<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /> 2C-MMDA-2 is also the phenethylamine [[structural analog|analogue]] of [[MMDA-2]].<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" />

'''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|5-HT₂ receptor]] [[agonist]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted methylenedioxyphenethylamine|methylenedioxyphenethylamine]] families.<ref name="PiHKAL">{{CitePiHKAL }} "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."</ref><ref name="Shulgin_2011">{{cite book | vauthors = Shulgin A, Manning T, Daley PF | title = [[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]] | location = Berkeley, CA | volume = 1 | pages = 339, 347 | year = 2011 | publisher = Transform Press | isbn = 978-0-9630096-3-0 | oclc = 709667010 }}</ref><ref name="Wallach_2023">{{cite journal | vauthors = Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nature Communications | volume = 14 | issue = 1 | pages = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | url = https://bitnest.netfirms.com/external/10.1038/s41467-023-44016-1 }}</ref> Along with [[lophophine]] (2C-MMDA-1 or MMDPEA-1), it is one of the [[positional isomer]]s of [[methoxymethylenedioxyphenethylamine]] (MMDPEA).<ref name="PiHKAL" /><ref name="Shulgin_2011" /> 2C-MMDA-2 is also the phenethylamine [[structural analog|analogue]] of [[MMDA-2]].<ref name="PiHKAL" /><ref name="Shulgin_2011" />

== Pharmacology ==

The drug is a [[full agonist]] of the serotonin [[5-HT2A receptor|5-HT_2A]], [[5-HT2B receptor|5-HT_2B]], and [[5-HT2C receptor|5-HT_2C receptor]]s.<ref name="WallachCaoCalkins2023" /> Its {{Abbrlink|EC₅₀|half-maximal effective concentration}} ({{Abbrlink|E_max|maximal efficacy}}) values were 148{{nbsp}}nM (102%) for [[Gq protein|G_q]] [[cell signaling|signaling]] and 589{{nbsp}}nM (107%) for [[β-arrestin2]] signaling at the serotonin 5-HT_2A receptor, 204{{nbsp}}nM (104%) at the serotonin 5-HT_2B receptor, and 9.77{{nbsp}}nM (109%) at the serotonin 5-HT_2C receptor.<ref name="WallachCaoCalkins2023" /> 2C-MMDA-2 was more [[potency (pharmacology)|potent]] as a serotonin 5-HT₂ receptor agonist than [[mescaline]].<ref name="WallachCaoCalkins2023" />

The drug is a [[full agonist]] of the serotonin [[5-HT2A receptor|5-HT_2A]], [[5-HT2B receptor|5-HT_2B]], and [[5-HT2C receptor|5-HT_2C receptor]]s.<ref name="Wallach_2023" /> Its {{Abbrlink|EC₅₀|half-maximal effective concentration}} ({{Abbrlink|E_max|maximal efficacy}}) values were 148{{nbsp}}nM (102%) for [[Gq protein|G_q]] [[cell signaling|signaling]] and 589{{nbsp}}nM (107%) for [[β-arrestin2]] signaling at the serotonin 5-HT_2A receptor, 204{{nbsp}}nM (104%) at the serotonin 5-HT_2B receptor, and 9.77{{nbsp}}nM (109%) at the serotonin 5-HT_2C receptor.<ref name="Wallach_2023" /> 2C-MMDA-2 was more [[potency (pharmacology)|potent]] as a serotonin 5-HT₂ receptor agonist than [[mescaline]].<ref name="Wallach_2023" />

[[Alexander Shulgin]] in 1963 tested 2C-MMDA-2 at doses of up to 2.6{{nbsp}}mg and observed no effects but did not try higher doses.<ref name="PiHKAL" /><ref name="Shulgin-Lab-Notes-1">https://isomerdesign.com/pihkal/notebooks/transcripts/p1/p1.75.pdf {{Bare URL PDF|date=July 2025}}</ref> 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.<ref name="PiHKAL" /> Later, 2C-MMDA-2 was assessed in terms of [[serotonin receptor]] activity by [[Jason Wallach]] and colleagues in 2023.<ref name="WallachCaoCalkins2023" />

== History ==

The [[NBOMe]] [[chemical derivative|derivative]] of 2C-MMDA-2 is [[2C2-NBOMe]].<ref name="WallachCaoCalkins2023" /> It is a highly [[potency (pharmacology)|potent]] serotonin 5-HT₂ receptor agonist and produces the [[head-twitch response]], a behavioral proxy of [[psychedelic drug|psychedelic]] effects, in rodents.<ref name="WallachCaoCalkins2023" />

[[Alexander Shulgin]] in 1963 tested 2C-MMDA-2 at doses of up to 2.6{{nbsp}}mg and observed no effects but did not try higher doses.<ref name="PiHKAL" /><ref name="Shulgin-Lab-Notes-1">{{cite web | title = Subacute effects of XV-106 | url = https://isomerdesign.com/pihkal/notebooks/transcripts/p1/p1.75.pdf | work = pihkal }}</ref> 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.<ref name="PiHKAL" /> Later, 2C-MMDA-2 was assessed in terms of [[serotonin receptor]] activity by [[Jason Wallach]] and colleagues in 2023.<ref name="Wallach_2023" />

== Analogs ==

The [[NBOMe]] [[chemical derivative|derivative]] of 2C-MMDA-2 is [[2C2-NBOMe]].<ref name="Wallach_2023" /> It is a highly [[potency (pharmacology)|potent]] serotonin 5-HT₂ receptor agonist and produces the [[head-twitch response]], a behavioral proxy of [[psychedelic drug|psychedelic]] effects, in rodents.<ref name="Wallach_2023" />

==See also==

==See also==