(R)-MDMA

(R)-MDMA
Clinical data
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[1][2]
Drug classSerotonin–norepinephrine releasing agent; Serotonin 5-HT2A receptor agonist; Entactogen; Empathogen[3][4]
Pharmacokinetic data
MetabolismCYP2D6[2]
Elimination half-life11–14 hours[1][2]
Identifiers
IUPAC name
  • (2R)-1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC11H15NO2
Molar mass193.246 g·mol−1
3D model (JSmol)
SMILES
  • C[C@H](CC1=CC2=C(C=C1)OCO2)NC
InChI
  • InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3/t8-/m1/s1
  • Key:SHXWCVYOXRDMCX-MRVPVSSYSA-N

(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.[3][2] Like MDMA, (R)-MDMA is an entactogen or empathogen.[3][2] It is taken by mouth.[3][2]

The drug is a serotonin–norepinephrine releasing agent (SNRA) and weak serotonin 5-HT2A receptor agonist.[3][4] It has substantially less or no significant dopamine-releasing activity compared to MDMA and (S)-MDMA.[3][4] 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.[3][5] In clinical studies, (R)-MDMA produces similar effects to MDMA and (S)-MDMA, but is less potent and has a longer duration.[1][2]

(R)-MDMA was first described in enantiopure form by 1978.[6] Under the developmental code names EMP-01, developed by atai Life Sciences,[7] and MM-402, developed by MindMed,[8] it is under development for the treatment of post-traumatic stress disorder (PTSD), social phobia, and pervasive development disorders (PDDs) such as autism.[9][10][11] It is thought that (R)-MDMA might have a better safety profile than MDMA itself whilst retaining its therapeutic benefits.[3]

  1. ^ a b c Cite error: The named reference Bedi2024 was invoked but never defined (see the help page).
  2. ^ a b c d e f g Cite error: The named reference StraumannAvedisianKlaiber2024 was invoked but never defined (see the help page).
  3. ^ a b c d e f g h Pitts EG, Curry DW, Hampshire KN, Young MB, Howell LL (February 2018). "(±)-MDMA and its enantiomers: potential therapeutic advantages of R(-)-MDMA". Psychopharmacology. 235 (2): 377–392. doi:10.1007/s00213-017-4812-5. PMID 29248945.
  4. ^ a b c Cite error: The named reference RothmanBaumann2006 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference CurryYoungTran2018 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference AndersonBraunBraun1978 was invoked but never defined (see the help page).
  7. ^ "atai Life Sciences Announces Positive Topline Results from Single Ascending Dose Phase 1 Study with EMP-01 (R-MDMA)".
  8. ^ "MM-402 by Mind Medicine MindMed for Autism Spectrum Disorder (ASD): Likelihood of Approval".
  9. ^ "EMP 01 (R-MDMA)". AdisInsight. 20 August 2024. Retrieved 28 October 2024.
  10. ^ "R(-)-Methylenedioxymetamfetamine (MM-402; R(-)-MDMA)". AdisInsight. 30 January 2024. Retrieved 28 October 2024.
  11. ^ "Delving into the Latest Updates on EMP-01 with Synapse". Synapse. 1 November 2024. Retrieved 2 November 2024.
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