MiPLA

Last updated
MiPLA
MIPLSD.svg
Clinical data
Other namesMiPLA; MIPLA; Lysergic acid methylisopropylamide; N-Methyl-N-isopropyllysergamide; LAMIDE; LA-Me/iso
Routes of
administration 		Oral [1] [2] [3]
Drug class Serotonin receptor modulator; 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of action 20–40 minutes [3]
Duration of action 4–6 hours [3]
Identifiers
  • (8β)-N-Isopropyl-N,6-dimethyl-9,10-didehydroergoline-8-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C20H25N3O
Molar mass 323.440 g·mol−1
3D model (JSmol)
  • C4N(C)C1Cc2c[nH]c(ccc3)c2c3C1=CC4C(=O)N(C)C(C)C
  • InChI=1S/C20H25N3O/c1-12(2)23(4)20(24)14-8-16-15-6-5-7-17-19(15)13(10-21-17)9-18(16)22(3)11-14/h5-8,10,12,14,18,21H,9,11H2,1-4H3
  • Key:ROICYBLUWUMJFF-UHFFFAOYSA-N
   (verify)

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). [5] [1] It is taken orally. [1] [2] 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. [5] [1] [6] It is only somewhat less potent than LSD as a psychedelic. [1] [2] MiPLA has been encountered as a novel designer drug. [1] [7] [8] [9]

Contents

Use and effects

MiPLA has about 33% to 50% of the potency of LSD in producing psychedelic effects in humans. [1] [2] 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. [1] [2] Elsewhere, the following has been described about the properties and effects of MiPLA: [3]

"The primary route of administration for MiPLA is orally. Users report that, despite its lower potency, the hallucinogenic effects of MiPLA are very similar to those of LSD. Users typically describe it as "...soft LSD..." However, some reports indicate that the after-effects are harsh and negative. Active doses range from 50 to 300 mcg, depending on the desired effects. Effects occur within 20 to 40 minutes and last for 4 to 6 hours. It is sold recreationally as blotters or powder." [3]

MiPLA and its homologue EiPLA are the only known simple N,N-dialkyllysergamides that approach the potency of LSD itself. [5] All other N,N-dialkyl analogues tested, including the dimethyl, dipropyl, methylethyl, and so on, are only around one-tenth as potent as LSD. [10] However, some N-monoalkyllysergamides, such as the sec-butyl and tert-butyl derivatives, were also found to show activity and potency comparable to LSD. [11] In addition, iPLA, the N-monoisopropyl derivative, is only slightly weaker than MiPLA. [12] [13]

Interactions

Pharmacology

Pharmacodynamics

MiPLA has been found to interact with serotonin receptors, including acting as an agonist of the serotonin 5-HT2A receptor. [14] [15] [5] [13] [1] [16] [17] [18] [19] It also interacts with the dopamine D1 and D2 receptors. [17] [16] The drug fully substitutes for LSD in rodent drug discrimination tests with only slightly lower potency than LSD. [13] [5] [1] [20] In addition, MiPLA produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, with about one-third the potency of LSD. [1] [20] The drug showed roughly the same potency in producing the head-twitch response as EcPLA. [1]

Chemistry

MiPLA, also known as N-methyl-N-isopropyllysergamide or as lysergic acid methylisopropylamide, is a substituted lysergamide and a structural isomer of lysergic acid diethylamide (LSD; N,N-diethyllysergamide), with the alkyl groups on the amide nitrogen having been subjected to a methylene shuffle. [6]

Synthesis

The chemical synthesis of MiPLA has been described. [11] [9]

Analogues

Analogues of MiPLA include iPLA, EiPLA, EPLA, EcPLA, DiPLA, LSB, and LSP, among others. [14] The ester derivatives 1P-MiPLA and 1cP-MiPLA are thought to be prodrugs of MiPLA. [6] [21] [22]

History

MiPLA was originally discovered and described by Albert Hofmann at Sandoz during the original structure–activity research into LSD, with Eli Lilly and Company filing a patent in 1956 and it being published in 1961. [11] It was subsequently investigated in more detail by the team led by David E. Nichols at Purdue University in the 1990s. [1] [13] [5] 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. [12] MiPLA was first encountered as a novel designer drug by 2018. [1] [7] [8] [9]

Society and culture

Austria

MiPLA is technically not illegal in Austria but it may fall in the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich) as an analogue of LSD.[ citation needed ]

France

MiPLA is illegal in France. [4]

Germany

MiPLA is controlled in Germany under the NpSG (New Psychoactive Substances Act) [23] as of July 18, 2019. [24] 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. [25]

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. [26]

United Kingdom

MiPLA is a controlled substance in the United Kingdom via the Psychoactive Substances Act 2016.[ citation needed ]

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.[ citation needed ] However, it may be a Schedule I controlled substance in the United States due to being a skeletal isomer [6] of LSD.[ citation needed ]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, Nichols DE, Brandt SD (February 2019). "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology (Berl). 236 (2): 799–808. doi:10.1007/s00213-018-5055-9. PMC   6848745 . PMID   30298278.
  2. 1 2 3 4 5 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]
  3. 1 2 3 4 5 "MIPLA (Метилизопропиллизергамид)". АИПСИН (in Russian). Retrieved 3 November 2025.
  4. 1 2 "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
  5. 1 2 3 4 5 6 Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE (March 1994). "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology Biochemistry and Behavior. 47 (3): 667–673. doi:10.1016/0091-3057(94)90172-4. PMID   8208787. S2CID   16490010.
  6. 1 2 3 4 Wachełko O, Nowak K, Tusiewicz K, Zawadzki M, Szpot P (January 2025). "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. doi:10.1039/d4an01361a. PMID   39636448.
  7. 1 2 Tanaka R, Kawamura M, Hakamatsuka T, Kikura-Hanajiri R (2020). "シート状危険ドラッグ製品中のLSD誘導体1cP-LSD, MIPLA, 1B-LSDの同定" [Identification of LSD Derivatives, 1cP-LSD, MIPLA and 1B-LSD in Illegal Products as Paper Sheet]. Yakugaku Zasshi (in Japanese). 140 (11): 1405–1413. doi:10.1248/yakushi.20-00124. PMID   33132277.
  8. 1 2 Brandt SD, Kavanagh PV, Westphal F, Stratford A, Blanckaert P, Dowling G, Grill M, Schwelm HM, Auwärter V, Chapman SJ (March 2022). "Separating the wheat from the chaff: Observations on the analysis of lysergamides LSD, MIPLA, and LAMPA". Drug Test Anal. 14 (3): 545–556. doi:10.1002/dta.3103. PMID   34022102.
  9. 1 2 3 Shoda T, Tsuji G, Kawamura M, Kurohara T, Misawa T, Kikura-Hanajiri R, Demizu Y (June 2024). "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. doi:10.1002/dta.3586. PMID   37830386.
  10. ↑ Hofmann A (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects" (PDF). Acta Physiologica et Pharmacologica Neerlandica. 8: 240–258. PMID   13852489.
  11. 1 2 3 USpatent 2997470,Pioch RP,"Lysergic Acid Amides",published 1956-03-05,issued 1961-08-22
  12. 1 2 Nichols DE (2001). "LSD and its lysergamide cousins" (PDF). The Heffter Review of Psychedelic Research. 2. Santa Fe, New Mexico: Heffter Research Institute: 80–87.
  13. 1 2 3 4 Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited" (PDF). NIDA Research Monograph. 146: 52–73. PMID   8742794. 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) [...]
  14. 1 2 Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN   978-3-662-55878-2. PMID   28401524.
  15. ↑ Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi: 10.1002/wmts.42 . ISSN   2190-460X.
  16. 1 2 Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB (April 1995). "LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors". Psychopharmacology (Berl). 118 (4): 401–409. doi:10.1007/BF02245940. PMID   7568626.
  17. 1 2 McCorvy JD (16 January 2013). Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics (Ph.D. thesis). Purdue University. Archived from the original on 15 May 2025. Retrieved 27 May 2025– via Purdue e-Pubs.{{cite thesis}}: CS1 maint: bot: original URL status unknown (link)
  18. ↑ Parrish JC (30 October 2007). "Toward a molecular understanding of hallucinogen action". Purdue e-Pubs.
  19. ↑ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest   304838368.
  20. 1 2 Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC   9191653 . PMID   31917152.
  21. ↑ Tusiewicz K, Wachełko O, Zawadzki M, Szpot P (December 2024). "Forensic Aspects of Designer LSD Analogs Identification by GC-MS (EI) and UV Spectroscopy". Molecules. 29 (23): 5717. doi: 10.3390/molecules29235717 . PMC   11643092 . PMID   39683876.
  22. ↑ Tanaka R, Kawamura M, Mizutani S, Kikura-Hanajiri R (July 2023). "Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products". Forensic Toxicol. 41 (2): 294–303. doi:10.1007/s11419-023-00661-1. PMC   10310582 . PMID   36809464.
  23. ↑ "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
  24. ↑ "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (PDF). Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27 (in German). Bundesanzeiger Verlag. July 17, 2019. pp. 1083–1094. Retrieved January 1, 2020.
  25. ↑ "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
  26. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.
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