DIPLA

Last updated

DIPLA
N,N-Diisopropyllysergamide.svg
Clinical data
Other namesDiPLA; N,N-Diisopropyllysergamide; Lysergic acid diisopropylamide
Drug class Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-7-methyl-N,N-di(propan-2-yl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
PubChem CID
Chemical and physical data
Formula C22H29N3O
Molar mass 351.494 g·mol−1
3D model (JSmol)
  • CN1C[C@@H](C=C2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)N(C(C)C)C(C)C
  • InChI=1S/C22H29N3O/c1-13(2)25(14(3)4)22(26)16-9-18-17-7-6-8-19-21(17)15(11-23-19)10-20(18)24(5)12-16/h6-9,11,13-14,16,20,23H,10,12H2,1-5H3/t16-,20-/m1/s1
  • Key:UGLFFFFNSMDCNO-OXQOHEQNSA-N

DIPLA, also known as N,N-diisopropyllysergamide or as lysergic acid diisopropylamide, is a putative serotonergic psychedelic of the lysergamide family related to lysergic acid diethylamide (LSD). [1] [2] [3] [4] It is the analogue of LSD in which the N,N-diethyl groups have been replaced with N,N-diisopropyl groups. [3] [2] [5]

Contents

Use and effects

DIPLA is not known to have been assessed in humans. [3] [6]

Pharmacology

In an early study, DIPLA showed 23.2% of the antiserotonergic activity of LSD in the isolated rat uterus and hence was about 4-fold less potent than LSD in this assay. [3] [4] [7] Subsequently, DIPLA was reported to have an affinity (Ki) for the serotonin 5-HT2A receptor of 9.0 to 20.2 nM, which was about 4- to 9-fold lower than that of LSD (Ki = 4.8 nM). [8] [2] [5] [9] It is an agonist of the serotonin 5-HT2A receptor and also interacts with other receptors such as the serotonin 5-HT1A receptor, the serotonin 5-HT2C receptor, and dopamine receptors. [8] [1] DIPLA fully substituted for LSD in rodent drug discrimination tests, suggesting that it could have psychedelic effects in humans. [2] [9] Unlike other assessed lysergamides however, DIPLA was much less potent than LSD, about 8-fold so in the drug discrimination test. [5] [9]

History

DIPLA was first described in the scientific literature by Albert Hofmann and colleagues by 1955. [10] [11] Subsequently, it was studied in more detail by David E. Nichols and colleagues in the 1990s and thereafter. [2] [5] [9] [1]

See also

References

  1. 1 2 3 Jain MK, Gumpper RH, Slocum ST, Schmitz GP, Madsen JS, Tummino TA, et al. (July 2025). "The polypharmacology of psychedelics reveals multiple targets for potential therapeutics" (PDF). Neuron. doi:10.1016/j.neuron.2025.06.012. PMID   40683247.
  2. 1 2 3 4 5 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. Although all N-isopropyl homologs have only 25 to 30 percent affinity of LSD for this site, it is interesting to note that the N-methyl-N-isopropyl compound discussed earlier has nearly equal affinity to LSD for the 5-HT2 site labeled with the agonist ligand [ 125I]-R-DOI. This illustrates the importance of determining the relative efficacy of these compounds rather than just receptor affinity. [...] TABLE 6. Radioligand binding data for N-methyl-N-isopropyl lysergamides: [ 3H]-ketanserin displacement (unpublished results).
  3. 1 2 3 4 Oberlender RA (May 1989). "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens". Purdue e-Pubs. Purdue University. Table 2. Relative potency values for lysergic acid amides. [...]
  4. 1 2 Cerletti A, Doepfner W (January 1958). "Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids". The Journal of Pharmacology and Experimental Therapeutics. 122 (1): 124–136. doi:10.1016/S0022-3565(25)11933-2. PMID   13502837. Archived from the original on 2025-06-30.
  5. 1 2 3 4 Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE (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 . Retrieved 27 July 2025.
  6. ↑ 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.
  7. ↑ Rothlin E (March 1957). "Lysergic acid diethylamide and related substances". Annals of the New York Academy of Sciences. 66 (3): 668–676. Bibcode:1957NYASA..66..668R. doi:10.1111/j.1749-6632.1957.tb40756.x. PMID   13425249. Archived from the original on 12 July 2025. Finally, we have the disubstituted amides of d-lysergic acid: the dimethyl, diethyl. di-isopropyl, and dibutyl amides. They are 3 to 5 times weaker than LSD in their antagonism toward serotonin.
  8. 1 2 Nichols DE (2017). "Chemistry and Structure–Activity Relationships of Psychedelics". Behavioral Neurobiology of Psychedelic Drugs. Current Topics in Behavioral Neurosciences. Vol. 36. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 1–43. doi:10.1007/7854_2017_475. ISBN   978-3-662-55878-2. PMID   28401524 . Retrieved 27 July 2025.{{cite book}}: |journal= ignored (help)
  9. 1 2 3 4 Nichols DE (2001). "LSD and Its Lysergamide Cousins" (PDF). The Heffter Review of Psychedelic Research. 2. Heffter Research Institute: 80–87. ISSN   1534-9640. Table 3. Affinity for 5-HT2A and 5-HT1A receptors and potency in the rat two-lever drug discrimination assay for selected lysergic acid amides. [...]
  10. ↑ Stoll A, Hofmann A (1955). "Amide der stereoisomeren Lysergsäuren und Dihydro-lysergsäuren. 38. Mitteilung über Mutterkornalkaloide" [Amides of stereoisomeric lysergic and dihydrolysergic acids. 38. Ergot alkaloids]. Helvetica Chimica Acta. 38 (2): 421–433. Bibcode:1955HChAc..38..421S. doi:10.1002/hlca.19550380207. ISSN   0018-019X.
  11. ↑ Hofmann A (June 1959). "Psychotomimetic Drugs: Chemical and Pharmacological Aspects" (PDF). Acta Physiologica et Pharmacologica Neerlandica. 8: 240–258. PMID   13852489.


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