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Entactogen

"empathogen" redirects here. For the album by Willow Smith, see Empathogen (album).
Entactogen
Drug class
A selection of MDMA pills, which are often nicknamed "Ecstasy" or "E"
Class identifiers
SynonymsEntactogen; Empathogen; Connectogen[1][2][3][4]
UseRecreational, spiritual, medical, microdosing
Mechanism of actionSerotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonism
Biological targetSerotonin transporter; Norepinephrine transporter; Dopamine transporter; Serotonin 5-HT2 receptors
Chemical classAmphetamines, MDxx, cathinones, benzofurans, α-alkyltryptamines, 2-aminoindanes, others
Legal status
Legal status
  • Variable
In Wikidata
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Entactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observed and reported for experiences with MDMA.[1][2][5][3][4] This class of drug is distinguished from the classes of hallucinogens or psychedelics and stimulants, although entactogens, for instance MDMA, can also have these properties.[1][4][6][7] Entactogens are used both as recreational drugs[8] and are being investigated for medical use in the treatment of psychiatric disorders, for instance MDMA-assisted therapy for post-traumatic stress disorder (PTSD).[9][10][11]

Notable members of this class include MDMA, MDA, MDEA, MDOH, MBDB, 5-APB, 5-MAPB, 6-APB, 6-MAPB, methylone, mephedrone, αMT, αET, and MDAI, among others.[1][5] Most entactogens are phenethylamines and amphetamines, although several, such as αMT and αET, are tryptamines.[1][5] When referring to MDMA and its counterparts, the term MDxx is often used (with the exception of certain non-entactogen drugs like MDPV).

Entactogens act as serotonin releasing agents (SRAs) as their key action.[12][13][5][14][15] However, entactogens also frequently have additional actions, such as induction of dopamine and norepinephrine and serotonin 5-HT2 receptor agonism, which contributes to their effects as well.[12][13][5][14][15] It is thought that dopamine and norepinephrine release provide additional stimulant, euphoriant, and cardiovascular or sympathomimetic effects, serotonin 5-HT2A receptor agonism produces psychedelic effects of variable intensity, and both dopamine release and serotonin 5-HT2 receptor agonism may enhance the entactogenic effects and be critically involved in allowing for the qualitative "magic" of these drugs.[12][13][5][14][15] Entactogens that simultaneously induce serotonin and dopamine release, for instance MDMA, are known to produce long-lasting serotonergic neurotoxicity[16][17][5] with associated cognitive and memory deficits as well as psychiatric changes.[18][19][20][21]

MDA and MDMA were both first synthesized independently in the early 1910s.[22] The psychoactive effects of MDA were discovered in 1930 but were not described until the 1950s, MDA and MDMA emerged as recreational drugs in the 1960s, and the unique entactogenic effects of MDMA were first described in the 1970s.[22][23][24][25][26] Entactogens as a unique pharmacological class depending on induction of serotonin release was established in the mid-1980s and novel entactogens such as MBDB were developed at this time and after.[1][4][6] Gordon Alles discovered the psychoactive effects of MDA,[25][26] Alexander Shulgin played a key role in bringing awareness to MDMA and its unique effects,[24] and Ralph Metzner[27][28][29] and David E. Nichols formally defined entactogens and established them as a distinct class of drugs.[1][4][6] Many entactogens like MDMA are controlled substances throughout the world.[30][31]

  1. ^ a b c d e f g Cite error: The named reference Nichols2022 was invoked but never defined (see the help page).
  2. ^ a b Cite error: The named reference StockerLiechti2024 was invoked but never defined (see the help page).
  3. ^ a b Nichols D, Yensen R, Metzner R, Shakespeare W (1993). "The Great Entactogen-Empathogen Debate" (PDF). Newsletter of the Multidisciplinary Association for Psychedelic Studies. 4 (2): 47–49.
  4. ^ a b c d e Cite error: The named reference Nichols1986 was invoked but never defined (see the help page).
  5. ^ a b c d e f g Cite error: The named reference Oeri2021 was invoked but never defined (see the help page).
  6. ^ a b c Nichols DE, Hoffman AJ, Oberlender RA, Jacob P, Shulgin AT (October 1986). "Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class". J Med Chem. 29 (10): 2009–2015. doi:10.1021/jm00160a035. PMID 3761319.
  7. ^ McGregor, Iain S.; Thompson, Murray R.; Callaghan, Paul D. (2010-01-01). Stolerman, Ian P. (ed.). Encyclopedia of Psychopharmacology. Springer Berlin Heidelberg. pp. 758–762. doi:10.1007/978-3-540-68706-1_154. ISBN 9783540686989.
  8. ^ Cite error: The named reference HillThomas2011 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Baldo2024 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference Singh2025 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference WolfgangFonzoGray2025 was invoked but never defined (see the help page).
  12. ^ a b c Cite error: The named reference Kamilar-BrittBedi2015 was invoked but never defined (see the help page).
  13. ^ a b c Cite error: The named reference HalberstadtNichols2020 was invoked but never defined (see the help page).
  14. ^ a b c Cite error: The named reference Baggott2023 was invoked but never defined (see the help page).
  15. ^ a b c Cite error: The named reference Baggott2024 was invoked but never defined (see the help page).
  16. ^ Baggott, Matthew; Mendelson, John (2001). "Does MDMA Cause Brain Damage?". In Holland, J. (ed.). Ecstasy: The Complete Guide: A Comprehensive Look at the Risks and Benefits of MDMA. Inner Traditions/Bear. pp. 110–145, 396–404. ISBN 978-0-89281-857-0.
  17. ^ Sprague JE, Everman SL, Nichols DE (June 1998). "An integrated hypothesis for the serotonergic axonal loss induced by 3,4-methylenedioxymethamphetamine". Neurotoxicology. 19 (3): 427–441. PMID 9621349.
  18. ^ Parrott AC (April 2002). "Recreational Ecstasy/MDMA, the serotonin syndrome, and serotonergic neurotoxicity". Pharmacol Biochem Behav. 71 (4): 837–844. doi:10.1016/s0091-3057(01)00711-0. PMID 11888574.
  19. ^ Parrott AC (September 2013). "MDMA, serotonergic neurotoxicity, and the diverse functional deficits of recreational 'Ecstasy' users". Neurosci Biobehav Rev. 37 (8): 1466–1484. doi:10.1016/j.neubiorev.2013.04.016. PMID 23660456.
  20. ^ Aguilar MA, García-Pardo MP, Parrott AC (January 2020). "Of mice and men on MDMA: A translational comparison of the neuropsychobiological effects of 3,4-methylenedioxymethamphetamine ('Ecstasy')". Brain Res. 1727: 146556. doi:10.1016/j.brainres.2019.146556. PMID 31734398.
  21. ^ Montgomery C, Roberts CA (January 2022). "Neurological and cognitive alterations induced by MDMA in humans" (PDF). Exp Neurol. 347: 113888. doi:10.1016/j.expneurol.2021.113888. PMID 34624331.
  22. ^ a b Passie, Torsten (29 June 2023). The History of MDMA. Oxford University Press. doi:10.1093/oso/9780198867364.001.0001. ISBN 978-0-19-886736-4.
  23. ^ Bernschneider-Reif S, Oxler F, Freudenmann RW (November 2006). "The origin of MDMA ("ecstasy")--separating the facts from the myth". Pharmazie. 61 (11): 966–972. PMID 17152992.
  24. ^ a b Benzenhöfer U, Passie T (August 2010). "Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin". Addiction. 105 (8): 1355–61. doi:10.1111/j.1360-0443.2010.02948.x. PMID 20653618.
  25. ^ a b Gordon A. Alles (1959). "Some Relations Between Chemical Structure and Physiological Action of Mescaline and Related Compounds / Structure and Action of Phenethylamines". In Abramson HA (ed.). Neuropharmacology: Transactions of the Fourth Conference, September 25, 26, and 27, 1957, Princeton, N. J. New York: Josiah Macy Foundation. pp. 181–268. OCLC 9802642. Archived from the original on 21 March 2025.
  26. ^ a b Gordon A. Alles (1959). "Subjective Reactions to Phenethylamine Hallucinogens". A Pharmacologic Approach to the Study of the Mind. Springfield: CC Thomas. pp. 238–250 (241–246). ISBN 978-0-398-04254-7. {{cite book}}: ISBN / Date incompatibility (help)
  27. ^ Eisner, Bruce (1989). "Chapter II. What is an Empathogen?". Ecstasy: The MDMA Story. Berkeley, California: Ronin Pub. pp. 33–50. ISBN 978-0-914171-25-6. OCLC 27935523. OL 2222596M. Archived from the original on 8 June 2023. Retrieved 25 April 2025.
  28. ^ Metzner, Ralph; Adamson, Sophia (2001). "Using MDMA in Healing, Psychotherapy, and Spiritual Practice". In Holland, J. (ed.). Ecstasy: The Complete Guide: A Comprehensive Look at the Risks and Benefits of MDMA. Inner Traditions/Bear. pp. 182–207. ISBN 978-0-89281-857-0. The term "empathogenic," meaning "generating a state of empathy," was independently proposed for these substances in 1983—84 by Ralph Metzner, a psychologist and psychopharmacologist, and David Nichols, a professor of medicinal chemistry at Purdue University. Nichols subsequently rejected the term and now prefers "entactogenic," meaning "touching within," for MDMA. We continue to use the term "empathogenic."
  29. ^ Ralph Metzner (May 1983). [Lecture presented at the Psychedelics and Spirituality Conference]. Psychedelics and Spirituality, University of California, Santa Babara, May 13–14, 1983. Another group of drugs are the phenethylamines, of which MDA [and MDMA] is an example. Instead of calling these "psychedelic drugs," I'd like to suggest the name "empathogenic." Empathogenic means "empathy generating." Everyone I've mentioned this name to thinks it is a good one. These drugs don't produce visions as LSD does. They don't produce multileveled thinking or objectivity toward your mind as LSD and the psychedelics do. They generate a profound state of empathy for self and other in the most general and profound terms. A state of empathy where the feeling is that the self, the other, and the world is basically good, is all right. This state can be referred to as the ground of being, the core of our being, a still point of our being. Then individuals using these substances in therapy can look at their own problems from the standpoint of stillness and empathy. They are able to do changework on themselves very rapidly, compared to ordinary therapy.
  30. ^ Shulgin, Alexander (1992). Controlled Substances: A Chemical and Legal Guide to the Federal Drug Laws. Ronin Pub. ISBN 978-0-914171-50-8. Retrieved 25 April 2025.
  31. ^ Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.

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