MMDA-2
Psychedelic drug
From Wikipedia, the free encyclopedia
MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families.[1][2] It is the 6-methoxy derivative of MDA and is a positional isomer of MMDA (5-methoxy-MDA).[1][2]
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| Other names | 2-Methoxy-4,5-methylenedioxyamphetamine; 6-Methoxy-3,4-methylenedioxyamphetamine; 6-Methoxy-MDA; 6-MeO-MDA |
| Routes of administration | Oral[1] |
| Drug class | Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Duration of action | 8–12 hours[1] |
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| Formula | C11H15NO3 |
| Molar mass | 209.245 g·mol−1 |
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Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MMDA-2's dose as 25 to 50 mg orally and its duration as 8 to 12 hours.[1][2] The effects of MMDA-2 have been reported to include enhanced awareness, empathy, and visual facilitation and distortion, as well as some side effects like gastrointestinal upset and appetite loss.[1] Shlgin states that MMDA-2 at a dose of 30 mg orally is very similar to MDA at a dose of 80 mg orally, and also remarks that it would be impossible for anyone to have a bad experience on the drug at that dose.[1] MMDA-2 is approximately 4- or 5-fold more potent than MMDA, which has a listed dose range of 100 to 250 mg orally.[1]
Interactions
Pharmacology
Pharmacodynamics
MMDA-2 is a moderately potent serotonin receptor agonist in the rat stomach fundus assay (A2 = 224 nM).[3] These serotonin receptors may correspond specifically to the serotonin 5-HT2B receptor.[4][5]
It has been found that MMDA-2, unlike MMDA but similarly to 6-methyl-MDA, is very weak or negligible at inducing the release of serotonin or dopamine in vitro.[6] Accordingly, it does not produce amphetamine-like responses in animals in drug discrimination studies.[7] Instead, MMDA-2 is likely to act as a pure serotonin 5-HT2 receptor agonist similarly to the DOx series of compounds, with activation of the serotonin 5-HT2A receptor believed to be responsible for its psychedelic effects.[8]
Chemistry
Synthesis
The chemical synthesis of MMDA-2 has been described.[1]
Analogues
Analogues of MMDA-2 include 2C-MMDA-2 (MMDPEA-2; 6-methoxy-MDPEA), MDA, MMDA (5-methoxy-MDA), MMDA-3a (2-methoxy-MDA), DMMDA-2 (5,6-dimethoxy-MDA; 5-methoxy-MMDA-2), methyl-MMDA-2 (N-methyl-MMDA-2; 6-methoxy-MDMA), EMDA-2 (6-ethoxy-MDA; 6-ethoxy-MMDA-2), 2C2-NBOMe (2C-MMDA-2-NBOMe; NBOMe-MMDPEA-2), F (5-methoxy-6-APDB), 4T-MMDA-2 (4-thio-MMDA-2), 6-methyl-MDA, 6-bromo-MDA (2-Br-4,5-MDA), and 6-chloro-MDA (2-Cl-4,5-MDA), among others.[1][2]
History
MMDA-2 was first described in the scientific literature by Alexander Shulgin in 1964.[9] Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[1] MMDA-2 was encountered as a novel designer drug by the 1990s.[10][11]
Society and culture
Legal status
Canada
MMDA-2 may be a controlled substance in Canada under phenethylamine blanket-ban language.[12]
United States
MMDA-2 is not an explicitly controlled substance in the United States, but may be considered scheduled as an isomer of MMDA.[13][14]