List of entactogens

This is a list of entactogens, or drugs that produce feelings of social connection and empathy.

Phenethylamines

Main article: Substituted phenethylamine

Amphetamines

Main article: Substituted amphetamine

Methylenedioxyamphetamines (benzodioxoles)

Main article: Substituted methylenedioxyphenethylamine

Benzofurans

Main article: Substituted benzofuran

Others

Cathinones

Main article: Substituted cathinone

Psychedelic phenethylamines

Cyclized phenethylamines

2-Aminoindanes

Main article: Substituted 2-aminoindane

2-Aminotetralins

Main article: Substituted 2-aminotetralin

Aminorexes

Main article: Substituted 2-amino-5-aryloxazoline

Tryptamines

Main article: Substituted tryptamine

5-Methoxytryptamines

α-Alkyltryptamines

Main article: Substituted α-alkyltryptamine

β-Keto-α-alkyltryptamines

Main article: Substituted β-ketotryptamine

Tryptamine bioisosteres

Isotryptamines

Main article: Substituted isotryptamine

Indolizines

Main article: Substituted indolizinylethylamine

See also

References

  1. ^ a b c d e f g h i j k l m n o p q Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy" (PDF). J Psychopharmacol. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493.
  2. ^ Kuypers KP, De Sousa Fernandes Perna EB, Theunissen EL, Toennes SW, Mason NL, Hutten NR, Ramaekers JG (2019). "A First-in-Man Study with 4-Fluoroamphetamine Demonstrates it Produces a Mild Psychedelic State". J Psychoactive Drugs. 51 (3): 225–235. doi:10.1080/02791072.2019.1569286. PMID 30676284.
  3. ^ Berquist MD, Leth-Petersen S, Kristensen JL, Fantegrossi WE (February 2020). "Locomotor effects of 3,4-methylenedioxymethamphetamine (MDMA) and its deuterated form in mice: psychostimulant effects, stereotypy, and sensitization". Psychopharmacology (Berl). 237 (2): 431–442. doi:10.1007/s00213-019-05380-3. PMC 7388080. PMID 31729537.
  4. ^ Berquist MD, Leth-Petersen S, Kristensen JL, Fantegrossi WE (March 2020). "In vivo effects of 3,4-methylenedioxymethamphetamine (MDMA) and its deuterated form in rodents: Drug discrimination and thermoregulation". Drug Alcohol Depend. 208 107850. doi:10.1016/j.drugalcdep.2020.107850. PMID 31954950.
  5. ^ a b c d e f g Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  6. ^ Straumann I, Vizeli P, Avedisian I, Erne L, Noorshams D, Vukalovic I, Eckert A, Luethi D, Rudin D, Liechti ME (September 2025). "Acute effects of MDMA, MDA, lysine-MDMA, and lysine-MDA in a randomized, double-blind, placebo-controlled, crossover trial in healthy participants". Neuropsychopharmacology. doi:10.1038/s41386-025-02248-3. PMID 40999236.
  7. ^ a b c Alberto-Silva AS, Hemmer S, Bock HA, da Silva LA, Scott KR, Kastner N, Bhatt M, Niello M, Jäntsch K, Kudlacek O, Bossi E, Stockner T, Meyer MR, McCorvy JD, Brandt SD, Kavanagh P, Sitte HH (September 2024). "Bioisosteric analogs of MDMA: Improving the pharmacological profile?". J Neurochem. 168 (9): 2022–2042. doi:10.1111/jnc.16149. PMC 11449655. PMID 38898705.
  8. ^ a b Kastner N, Nadal-Gratacós N, Hemmer S, Alves da Silva L, McKee JL, Hell T, Cicalese G, Holy M, Kooti F, Jäntsch K, Baron R, Shacham N, Cuccurazzu B, Halberstadt AL, McCorvy JD, Stockner T, Meyer MR, López-Arnau R, Grill M, Sitte HH (December 2025). "Next-Generation MDMA Analogue SDMA: Pharmacological and Metabolic Insights". ACS Chem Neurosci. 16 (24): 4725–4740. doi:10.1021/acschemneuro.5c00782. PMID 41329099.
  9. ^ a b Gatch MB, Dolan SB, Forster MJ (June 2020). "Methylenedioxymethamphetamine-like discriminative stimulus effects of seven cathinones in rats". Behav Pharmacol. 31 (4): 378–384. doi:10.1097/FBP.0000000000000540. PMC 11562892. PMID 31895060.
  10. ^ Luethi D, Liechti ME (April 2020). "Designer drugs: mechanism of action and adverse effects". Arch Toxicol. 94 (4): 1085–1133. Bibcode:2020ArTox..94.1085L. doi:10.1007/s00204-020-02693-7. PMC 7225206. PMID 32249347. In one of the few clinical studies of a designer drug, 4-bromo-2,5-dimethoxyphenylethylamine (2C-B) was shown to induce euphoria, well-being, and changes in perception, and to have mild stimulant properties (Gonzalez et al. 2015). 2C-B may thus be classified as a psychedelic with entactogenic properties, an effect profile that is similar to various other phenethylamine psychedelics (Shulgin and Shulgin 1995).
  11. ^ Wills B, Erickson T (9 March 2012). "Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives". In Barceloux DG (ed.). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. Wiley. pp. 156–192. doi:10.1002/9781118105955.ch10. ISBN 978-0-471-72760-6. DOSE EFFECT: Anecdotal data suggests that recreational doses of 2C-B range from 4—30 mg with lower doses (4—10 mg) producing entactogenic effects, whereas high doses (10— 20 mg) cause psychedelic and sympathomimetic effects.
  12. ^ González D, Torrens M, Farré M (2015-10-12). "Acute Effects of the Novel Psychoactive Drug 2C-B on Emotions". BioMed Research International. 2015 643878. doi:10.1155/2015/643878. PMC 4620274. PMID 26543863.
  13. ^ a b Nichols DE, Brewster WK, Johnson MP, Oberlender R, Riggs RM (February 1990). "Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA)". J Med Chem. 33 (2): 703–710. doi:10.1021/jm00164a037. PMID 1967651.
  14. ^ a b c Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  15. ^ Shulgin AT, Carter MF (1980). "N, N-Diisopropyltryptamine (DIPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT). Two orally active tryptamine analogs with CNS activity". Commun Psychopharmacol. 4 (5): 363–369. PMID 6949674.
  16. ^ a b Palamar JJ, Acosta P (January 2020). "A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines". Hum Psychopharmacol. 35 (1) e2719. doi:10.1002/hup.2719. PMC 6995261. PMID 31909513. [...] These increased sensations of touch [with 5-methoxytryptamines like 5-MeO-DiPT and 5-MeO-MiPT] are likely why some users compared the "body high" with the high associated with MDMA use. [...] I would actually say that it is closer to MDMA in its effects. The whole series of 5-MeO and 4-MeO … they're both very closely related in their effects so it tends to be a body high kind of thing. At higher doses it can get more psychedelic, but it's not that psychedelic. [...]
  17. ^ Carpenter DE (2022-01-25). "DEA Proposes Adding Five Psychedelic Compounds to Schedule 1". Lucid News. Retrieved 2022-01-26. Baggott says his team regularly uses one of the compounds on the list in his lab. "When my team synthesizes and characterizes a new compound, we need to compare it to compounds with known effects. We use 5-MeO-MiPT as one of these known comparison compounds," he says. "It is scientifically interesting to my team because, although it has classical psychedelic effects at higher doses, it has some MDMA-like effects at low doses."
  18. ^ a b WO 2022061242, Baggott M, "Advantageous tryptamine compositions for mental disorders or enhancement", published 2023 March 24, assigned to Tactogen 


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