Substituted ethylenedioxyphenethylamine

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EDMA, a notable psychoactive EDxx compound. Ethylenedioxymethamphetamine.svg
EDMA, a notable psychoactive EDxx compound.

The substituted ethylenedioxyphenethylamines (EDxx) are a small group of psychoactive drugs of the phenethylamine family related to the substituted methylenedioxyphenethylamines (MDxx). [1] [2] [3] They include the amphetamines 3,4-ethylenedioxyamphetamine (EDA), 3,4-ethylenedioxy-N-methylamphetamine (EDMA; "MDMC"), and 3-methoxy-4,5-ethylenedioxyamphetamine (MEDA; 5-methoxy-EDA) and the cathinone 3,4-ethylenedioxymethcathinone (EDMC), among others. [1] [2] [3]

Contents

EDxx compounds have been found act as monoamine releasing agents, including of serotonin, norepinephrine, and/or dopamine. [4] [5] [6] [7] [8] However, they showed reduced potency in these assays compared to their MDxx counterparts like MDMA, MMDA (5-methoxy-MDA), and methylone (MDMC). [4] [5] [6] [7] [8] Some, such as EDMA, have been assessed and variably found to produce psychoactive effects in humans. [1] [2] These effects have included paresthesia, nystagmus, sedation, hypnagogic imagery, and/or mild visual effects. [1] However, at assessed doses, there were no entactogenic or stimulant effects and no or only mild hallucinogenic effects at best, which led to conclusions that they were essentially inactive. [1] [2] [3]

EDxx compounds were tested by Alexander Shulgin and described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [1] [2] [3] They were first described in the scientific literature by Shulgin by 1964. [9] [10] [11]

Use and effects

See also

References

  1. 1 2 3 4 5 6 7 8 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628.
  2. 1 2 3 4 5 6 7 Shulgin A, Manning T, Daley PF (2011). "#65. EDA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. pp. 136–137. ISBN   978-0-9630096-3-0.
  3. 1 2 3 4 5 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN   978-0-12-433951-4. Archived from the original on 13 July 2025.
  4. 1 2 McKenna DJ, Guan XM, Shulgin AT (March 1991). "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacology, Biochemistry, and Behavior. 38 (3): 505–512. doi: 10.1016/0091-3057(91)90005-M . PMID   1829838. S2CID   2740262.
  5. 1 2 Del Bello F, Sakloth F, Partilla JS, Baumann MH, Glennon RA (September 2015). "Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine". Bioorganic & Medicinal Chemistry. 23 (17): 5574–5579. doi:10.1016/j.bmc.2015.07.035. PMC   4562428 . PMID   26233799.
  6. 1 2 Sakloth F (11 December 2015). Psychoactive synthetic cathinones (or 'bath salts'): Investigation of mechanisms of action (Ph.D. thesis). Virginia Commonwealth University. Retrieved 19 January 2025– via VCU Scholars Compass.
  7. 1 2 Glennon RA, Dukat M (2017). "Structure-Activity Relationships of Synthetic Cathinones". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. pp. 19–47. doi:10.1007/7854_2016_41. ISBN   978-3-319-52442-9. PMC   5818155 . PMID   27830576. Expansion of the methylenedioxy ring of methylone (24) to an ethylenedioxy ring (i.e., ethylenedioxymethcathinone, EDMC; 30; Figure 7) decreased its potency as a releasing agent at all three transporters by 2- to 3-fold (Del Bello et al., 2015).
  8. 1 2 Yadav BJ (16 July 2019). Understanding Structure–Activity Relationship of Synthetic Cathinones (Bath Salts) Utilizing Methylphenidate. Theses and Dissertations (Ph.D. thesis). Virginia Commonwealth University. doi:10.25772/MJQW-8C64 . Retrieved 24 November 2024– via VCU Scholars Compass. 8 In another study conducted by Del Bello et al.89 it was found that expansion of the methylenedioxy ring of MDMC (27) to an ethylenedioxy ring (EDMC, 31, Figure 14) slightly reduced its potency as a releasing agent at all three transporters.
  9. ↑ Shulgin AT (March 1964). "3-Methoxy-4,5-methylenedioxy Amphetamine, a New Psychotomimetic Agent". Nature. 201 (4924): 1120–1121. Bibcode:1964Natur.201.1120S. doi:10.1038/2011120a0. PMID   14152788. Archived from the original on 2025-07-12.
  10. ↑ Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure–activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. Bibcode:1969Natur.221..537S. doi:10.1038/221537a0. PMID   5789297. Archived from the original on 2025-07-12.
  11. ↑ Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN   978-1-4757-0512-6.
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