DMMDA-2
Psychedelic drug
From Wikipedia, the free encyclopedia
DMMDA-2, also known as 2,3-dimethoxy-4,5-methylenedioxyamphetamine or as 5,6-dimethoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to MDA.[1] It is the derivative of MDA with methoxy groups at the 5 and 6 positions and of MMDA and MMDA-2 with an additional methoxy group at either of these positions.[1]
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| Other names | 2,3-Dimethoxy-4,5-methylenedioxyamphetamine; 5,6-Dimethoxy-MDA; 3,4-Methylenedioxy-5,6-dimethoxyamphetamine; 5,6-Dimethoxy-3,4-methylenedioxyamphetamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonergic psychedelic; Hallucinogen; Serotonin releasing agent |
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| Duration of action | Unknown[1] |
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| Formula | C12H17NO4 |
| Molar mass | 239.271 g·mol−1 |
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| Melting point | 178 to 180 °C (352 to 356 °F) |
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Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DMMDA-2's dose as about 50 mg orally and its duration as unknown.[1] Threshold effects are said to occur at a dose of 28 mg (~0.4 mg/kg) or 30 to 50 mg orally.[1][2][3] In earlier publications, Shulgin listed its dose range as approximately 0.6 to 1 mg/kg (or ~42–70 mg for a 70-kg person) orally.[3][4][5] In a subsequent publication, he listed its dose as greater than 50 mg orally.[6]
Information on the properties and effects of DMMDA-2 in humans is sparse and its specific effects were not described, but it has been said to be "much like MDA" and to have similar effects as DMMDA.[1][2][7][3] The effects of DMMDA and DMMDA-2 may reportedly be different from those of other related psychedelics like mescaline, MMDA, and MMDA-2.[7][3] DMMDA-2 has approximately 5 times the potency of mescaline.[1][3][8][4][5][2][9][10] It is more potent than MDA but less potent than DMMDA.[6][5][10][1]
Interactions
Pharmacology
Pharmacodynamics
DMMDA-2 showed reduced albeit significant activity as a serotonin releasing agent compared to certain related compounds like MDA and MMDA.[11] It showed no activity as a dopamine releasing agent, in contrast to MDA but similarly to MMDA and MMDA-2.[11] Whereas DMMDA-2 significantly induced serotonin release, MMDA-2 was inactive in terms of serotonin and dopamine release induction.[11]
Chemistry
Synthesis
The chemical synthesis of DMMDA-2 has been described.[1][3] It can be synthesized from dillapiole.[1][3]
Analogues
A variety of positional isomers of DMMDA-2 are possible and/or known, such as DMMDA among others.[1] Other analogues of DMMDA-2 are also known, such as MMDA-2 among others.[1]
History
DMMDA-2 was first described in the scientific literature by Alexander Shulgin and colleagues in 1967.[3][12][8][13][14] However, Shulgin did not synthesize or test it himself.[1] Subsequently, the drug was described in greater detail by Shulgin in PiHKAL in 1991.[1]
Society and culture
Legal status
DMMDA-2 is a controlled substance in Canada under phenethylamine blanket-ban language.[15]