(R)-MDMA
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| Other names | (R)-Methylenedioxy-methamphetamine; (R)-MDMA; (R)-(–)-MDMA; R(–)-MDMA; (–)-MDMA; (R)-Midomafetamine; (R)-(–)-Midomafetamine; (–)-Midomafetamine; Armidomafetamine; levo-MDMA; l-MDMA; EMP-01; EMP01; MM-402; MM402 |
| Routes of administration | Oral |
| Drug class | Serotonin–norepinephrine releasing agent; Serotonin 5-HT2A receptor agonist; Entactogen; Empathogen |
| Pharmacokinetic data | |
| Metabolism | CYP2D6 |
| Elimination half-life | 11–14 hours |
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| Chemical and physical data | |
| Formula | C11H15NO2 |
| Molar mass | 193.246 g·mol−1 |
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(R)-3,4-Methylenedioxy-N-methylamphetamine ((R)-MDMA), also known as (R)-midomafetamine or as levo-MDMA, is the (R)- or levorotatory (l-) enantiomer of 3,4-methylenedioxy-N-methylamphetamine (MDMA; midomafetamine; "ecstasy"), a racemic mixture of (R)-MDMA and (S)-MDMA. Like MDMA, (R)-MDMA is an entactogen or empathogen. It is taken by mouth.
The drug is a serotonin–norepinephrine releasing agent (SNRA) and weak serotonin 5-HT2A receptor agonist. It has substantially less or no significant dopamine-releasing activity compared to MDMA and (S)-MDMA. In preclinial studies, (R)-MDMA shows equivalent therapeutic-like effects to MDMA, such as increased prosocial behavior, but shows reduced psychostimulant-like effects, addictive potential, and serotonergic neurotoxicity. In clinical studies, (R)-MDMA produces similar effects to MDMA and (S)-MDMA, but is less potent and has a longer duration.
(R)-MDMA was first described in enantiopure form by 1978. Under the developmental code names EMP-01, developed by atai Life Sciences, and MM-402, developed by MindMed, it is under development for the treatment of post-traumatic stress disorder (PTSD), social phobia, and pervasive development disorders (PDDs) such as autism. It is thought that (R)-MDMA might have a better safety profile than MDMA itself whilst retaining its therapeutic benefits.