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2C-MMDA-2

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2C-MMDA-2
Clinical data
Other names2C-2; MMDPEA-2; 6-Methoxy-MDPEA; 2-Methoxy-4,5-methylenedioxyphenethylamine
Drug classSerotonin 5-HT2 receptor agonist
ATC code
  • None
Identifiers
  • 2-(6-methoxy-1,3-benzodioxol-5-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC10H13NO3
Molar mass195.218 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(C=C1CCN)OCO2
  • InChI=1S/C10H13NO3/c1-12-8-5-10-9(13-6-14-10)4-7(8)2-3-11/h4-5H,2-3,6,11H2,1H3
  • Key:VHBCQDKBQRHHPZ-UHFFFAOYSA-N

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.[1][2][3] Along with lophophine (2C-MMDA-1 or MMDPEA-1), it is one of the positional isomers of methoxymethylenedioxyphenethylamine (MMDPEA).[1][2] 2C-MMDA-2 is also the phenethylamine analogue of MMDA-2.[1][2]

Use and effects

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In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin described testing 2C-MMDA-2 at doses of up to 2.6 mg and observed no effects but did not try higher doses.[1][4]

Pharmacology

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The drug is a full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[3] Its EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) values were 148 nM (102%) for Gq signaling and 589 nM (107%) for β-arrestin2 signaling at the serotonin 5-HT2A receptor, 204 nM (104%) at the serotonin 5-HT2B receptor, and 9.77 nM (109%) at the serotonin 5-HT2C receptor.[3] 2C-MMDA-2 was more potent as a serotonin 5-HT2 receptor agonist than mescaline.[3]

Chemistry

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Analogues

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The NBOMe derivative of 2C-MMDA-2 is 2C2-NBOMe.[3] It is a highly potent serotonin 5-HT2 receptor agonist and produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[3]

History

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Alexander Shulgin in tested 2C-MMDA-2 in 1963.[1][4] 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.[1] Later, 2C-MMDA-2 was assessed in terms of serotonin receptor activity by Jason Wallach and colleagues in 2023.[3]

See also

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References

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  1. ^ a b c d e f Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "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."
  2. ^ a b c Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 339, 347. ISBN 978-0-9630096-3-0. OCLC 709667010.
  3. ^ a b c d e f g Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nature Communications. 14 (1) 8221. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
  4. ^ a b "Subacute effects of XV-106" (PDF). pihkal.
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