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| Clinical data | |
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| Other names | 4-MeO-2,3-MDA; 4-Methoxy-2,3-methylenedioxyamphetamine; 2,3-Methylenedioxy-4-methoxyamphetamine; 4-Methoxy-ORTHO-MDA; 4-MeO-ORTHO-MDA |
| Routes of administration | Oral[1] |
| Drug class | Serotonergic psychedelic;Hallucinogen;Serotonin releasing agent |
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| Pharmacokinetic data | |
| Onset of action | Unknown[1] |
| Duration of action | Unknown[1] |
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| Chemical and physical data | |
| Formula | C11H15NO3 |
| Molar mass | 209.245 g·mol−1 |
| 3D model (JSmol) | |
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MMDA-3b, also known as4-methoxy-2,3-methylenedioxyamphetamine (4-MeO-2,3-MDA), is apsychedelic drug of thephenethylamine,amphetamine, andMDxx families related toORTHO-MDA (2,3-MDA).[2][1] It is the 4-methoxyderivative of ORTHO-MDA and is apositional isomer ofMMDA (5-MeO-3,4-MDA) and related compounds likeMMDA-2 (6-MeO-3,4-MDA) andMMDA-3a (2-MeO-3,4-MDA).[1]
MMDA-3b was included as an entry inAlexander Shulgin's bookPiHKAL (Phenethylamines I Have Known and Loved).[1] He lists its dose as greater than 80 mgorally and itsduration as unknown.[1][3] Shulgin describes 60 mg as being definitely active, qualitatively like3,4-methylenedioxyamphetamine (MDA), but quantitatively perhaps less, whereas an 80 mg dose of MMDA-3b was said to be no more effective than the 60 mg dose.[1] He also says that it is similar at these doses to 20 mg MMDA-3a and may be about 3-fold lesspotent than MMDA-3a.[1] Elsewhere, MMDA-3b is described as 3-fold more potent thanmescaline.[4] Little is known about the drug.[1] Thechemical synthesis of MMDA-3b was also described inPiHKAL.[1]
MMDA-3b has been found to act as anefficaciousserotonin releasing agent with little effect ondopamine similarly to MMDA.[5] For comparison, MDA andMDMA release both serotonin and dopamine, whereas MMDA-2 releases neither serotonin nor dopamine.[5]
MMDA-3b was first described in thescientific literature by Shulgin in 1964.[6] It was subsequently described in greater detail by Shulgin in his bookPiHKAL in 1991.[1] Other 2,3-MDA positional isomers of MMDA-3b includeMMDA-4 andMMDA-5.[2][1]
A more extensive study (Shulgin, 1964b) confirmed these findings and suggested that the activities of 2-methoxy-4,5-methylenedioxyamphetamine (3.19) and 2-methoxy-3,4-methylenedioxyamphetamine (3.20) were as high as 21 and 18 times that of mescaline although these figures have been revised to 12 and 10, respectively (Shulgin and others, 1969). Activity is somewhat reduced when the methylenedioxy group is in other positions, 2,3-methylenedioxy-4-methoxyamphetamine (3.21) being only three times as potent as mescaline, and the importance of the 2-methoxy group in the series is again emphasized by the low equipotency of 3,4-methylenedioxyamphetamine (3.17) and 3-methoxy-4,5-methylenedioxyamphetamine (3.18) compared to the high potency of compounds containing this substituent (3.19, 3.20) (Table 3.4). Most of these compounds produce a typical mescaline syndrome, particularly of closed-eye imagery (Shulgin, Sargent, and Naranjo, 1973), [...]