Chemistry:MiPLA

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MiPLA, also known as N-methyl-N-isopropyllysergamide or as lysergic acid methylisopropylamide, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).[1][2] It is taken orally.[2][3] The drug is a structural isomer of LSD in which the N,N-diethyl groups have been replaced with N-methyl and N-isopropyl groups.[1][2][4] It is only somewhat less potent than LSD.[2][3]

Use and effects

MiPLA has about one-third to one-half of the potency of LSD in producing psychedelic effects in humans.[2][3] According to Alexander Shulgin, it produced LSD-like effects at a dose of 180 to 300 μg orally, compared to a dose range of 60 to 200 μg in the case of LSD.[2][3]

MiPLA and its homologue EiPLA are the only known simple N,N-dialkyllysergamides that approach the potency of LSD itself.[1] All other N,N-dialkyl analogues tested, including the dimethyl, dipropyl, methylethyl, and so on, are only around one-tenth as potent as LSD.[5] However, some N-monoalkyllysergamides, such as the sec-butyl and tert-butyl derivatives, were also found to show activity and potency comparable to LSD.[6] In addition, iPLA, the N-monoisopropyl derivative, is only slightly weaker than MiPLA.[7][8]

Interactions

Pharmacology

Pharmacodynamics

MiPLA has been found to interact with serotonin receptors, including acting as an agonist of the serotonin 5-HT2A receptor.[9][8][2] It fully substitutes for LSD in rodent drug discrimination tests with only slightly lower potency than LSD.[8][2] In addition, MiPLA produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, with about one-third the potency of LSD.[2] The drug showed roughly the same potency in producing the head-twitch response as EcPLA.[2]

Chemistry

MiPLA is a structural isomer of LSD, with the alkyl groups on the amide nitrogen having been subjected to a methylene shuffle.[4]

Synthesis

The chemical synthesis of MiPLA has been described.[10]

Analogues

Analogues of MiPLA include iPLA, EiPLA, EPLA, EcPLA, DiPLA, LSB, and LSP, among others.[9] The ester derivatives 1P-MiPLA and 1cP-MiPLA are thought to be prodrugs of MiPLA.[4][11][12]

History

MiPLA was originally discovered and described by Albert Hofmann at Sandoz during the original structure–activity research into LSD.[6] It has subsequently been investigated in more detail by the team led by David E. Nichols at Purdue University.[2][1] The main use for this drug has been in studies of the binding site at the serotonin 5-HT2A receptor through which LSD produces its hallucinogenic effects.[7] MiPLA was first encountered as a novel designer drug by 2018.[2]

Society and culture

Austria

France

MiPLA is illegal in France.[13]

Germany

MiPLA is controlled in Germany under the NpSG (New Psychoactive Substances Act)[14] as of July 18, 2019.[15] Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.[16]

Switzerland

MiPLA can be considered a controlled substance in Switzerland as a defined derivative of Lysergic Acid under Verzeichnis E point 263. It is legal when used for scientific or industrial use.[17]

United Kingdom

United States

MiPLA is not scheduled in the United States but may be considered to be an analogue of LSD, which would make it illegal to possess for human consumption under the Federal Analogue Act. However, it may be a Schedule I controlled substance in the United States due to being a skeletal isomer[4] of LSD.{{Citation needed|date=October 2025}

See also

  • Substituted lysergamide
  • Lizard Labs

References

  1. ↑ 1.0 1.1 1.2 1.3 "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology Biochemistry and Behavior 47 (3): 667–673. March 1994. doi:10.1016/0091-3057(94)90172-4. PMID 8208787. 
  2. ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 2.10 2.11 "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology (Berl) 236 (2): 799–808. February 2019. doi:10.1007/s00213-018-5055-9. PMID 30298278. 
  3. ↑ 3.0 3.1 3.2 3.3 Shulgin AT (2016) Pharmacology notebook 9. Available online: https://www.erowid.org/library/books_online/shulgin_labbooks/shulgin_pharmacology_notebook9_searchable.pdf [Accessed: January 20, 2018]
  4. ↑ 4.0 4.1 4.2 4.3 "A highly sensitive UHPLC-MS/MS method for determining 15 designer LSD analogs in biological samples with application to stability studies". Analyst 150 (2): 290–308. January 2025. doi:10.1039/d4an01361a. PMID 39636448. 
  5. ↑ "Psychotomimetic drugs; chemical and pharmacological aspects". Acta Physiologica et Pharmacologica Neerlandica 8: 240–258. June 1959. PMID 13852489. https://www.samorini.it/doc1/alt_aut/ek/hofmann-psychotomimetic-drugs.pdf. 
  6. ↑ 6.0 6.1 Pioch RP, "Lysergic Acid Amides", US patent 2997470, published 1956-03-05, issued 1961-08-22
  7. ↑ 7.0 7.1 "LSD and its lysergamide cousins.". The Heffter Review of Psychedelic Research (Santa Fe, New Mexico: Heffter Research Institute) 2: 80–87. 2001. https://www.thevespiary.org/rhodium/Rhodium/Vespiary/talk/files/5022-chap6c758.pdf. 
  8. ↑ 8.0 8.1 8.2 "Lysergamides revisited". NIDA Research Monograph 146: 52–73. 1994. PMID 8742794. https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=57. "The series of isopropyl amides has recently been completed with the synthesis of the N-isopropyl, in addition to the N-methyl-N-isopropyl, N-ethyl-N-isopropyl, and the N,N-diisopropyl, as shown in figure 12. With the exception of the N,N-diisopropylamide, all compounds completely substitute in the DD paradigm in rats trained to discriminate LSD from saline. In table 6, the receptor-binding data for displacement of [3H]-ketanserin from rat cortical homogenate are shown. [...] TABLE 6. Radioligand binding data for N-methyl-N-isopropyl lysergamides: [3H]-ketanserin displacement (unpublished results) [...]". 
  9. ↑ 9.0 9.1 Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. 36. 2018. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. https://bitnest.netfirms.com/external/10.1007/7854_2017_475. 
  10. ↑ "Structural analysis of an lysergic acid diethylamide (LSD) analogue N-methyl-N-isopropyllysergamide (MiPLA): Insights from Rotamers in NMR spectra". Drug Test Anal 16 (6): 588–594. June 2024. doi:10.1002/dta.3586. PMID 37830386. 
  11. ↑ "Forensic Aspects of Designer LSD Analogs Identification by GC-MS (EI) and UV Spectroscopy". Molecules 29 (23): 5717. December 2024. doi:10.3390/molecules29235717. PMID 39683876. 
  12. ↑ "Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products". Forensic Toxicol 41 (2): 294–303. July 2023. doi:10.1007/s11419-023-00661-1. PMID 36809464. 
  13. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named LegiFrance
  14. ↑ "Anlage NpSG" (in de). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. https://www.gesetze-im-internet.de/npsg/anlage.html. 
  15. ↑ "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (in de). Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27. Bundesanzeiger Verlag. July 17, 2019. pp. 1083–1094. http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl119s1083.pdf. 
  16. ↑ "§ 4 NpSG" (in de). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. https://www.gesetze-im-internet.de/npsg/__4.html. 
  17. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in de). Bundeskanzlei [Federal Chancellery of Switzerland]. https://www.admin.ch/opc/de/classified-compilation/20101220/index.html. 

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