2C-MMDA-2
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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]
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| Other names | 2C-2; MMDPEA-2; 6-Methoxy-MDPEA; 2-Methoxy-4,5-methylenedioxyphenethylamine |
| Drug class | Serotonin 5-HT2 receptor agonist |
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| Formula | C10H13NO3 |
| Molar mass | 195.218 g·mol−1 |
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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
Pharmacodynamics
2C-MMDA-2 is a full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[3] Its EC50 (Emax) 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
- Substituted methylenedioxyphenethylamine
- Substituted methoxyphenethylamine
- Methoxymethylenedioxyphenethylamine
- Lophophine (2C-MMDA-1 or MMDPEA-1)
- 2C-MMDA-3a (MMDPEA-3a)
- 2C2-NBOMe (2C-MMDA-2-NBOMe)