2C-MMDA-2

Last updated

2C-MMDA-2
2C-MMDA-2.svg
Clinical data
Other names2C-2; MMDPEA-2; 6-Methoxy-MDPEA; 2-Methoxy-4,5-methylenedioxyphenethylamine
Drug class Serotonin 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
Formula C10H13NO3
Molar mass 195.218 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]

Contents

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 2.6 mg and observed no effects but did not try higher doses. [1] [4]

Pharmacology

The drug is a full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [3] Its EC50 Tooltip half-maximal effective concentration (Emax Tooltip 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

Analogues

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

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

References

  1. 1 2 3 4 5 6 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. 1 2 3 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. 1 2 3 4 5 6 7 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. Bibcode:2023NatCo..14.8221W. doi:10.1038/s41467-023-44016-1. PMC   10724237 . PMID   38102107.
  4. 1 2 "Subacute effects of XV-106" (PDF). pihkal.
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