2C-MMDA-2

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]

2C-MMDA-2

Clinical data
Other names	2C-2; MMDPEA-2; 6-Methoxy-MDPEA; 2-Methoxy-4,5-methylenedioxyphenethylamine
Drug class	Serotonin 5-HT2 receptor agonist
ATC code	None
Identifiers
IUPAC name 2-(6-methoxy-1,3-benzodioxol-5-yl)ethanamine
CAS Number	497096-69-2
PubChem CID	21831819
ChemSpider	13802346
Chemical and physical data
Formula	C10H13NO3
Molar mass	195.218 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC2=C(C=C1CCN)OCO2
InChI 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

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-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[3] Its EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy) values were 148 nM (102%) for G_q signaling and 589 nM (107%) for β-arrestin2 signaling at the serotonin 5-HT_2A receptor, 204 nM (104%) at the serotonin 5-HT_2B receptor, and 9.77 nM (109%) at the serotonin 5-HT_2C 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

• Substituted methylenedioxyphenethylamine
• Substituted methoxyphenethylamine
• Methoxymethylenedioxyphenethylamine
• Lophophine (2C-MMDA-1 or MMDPEA-1)
• 2C2-NBOMe (2C-MMDA-2-NBOMe)