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| Other names | MiPLA; 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 |
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| Pharmacokinetic data | |
| Onset of action | 20–40 minutes[3] |
| Duration of action | 4–6 hours[3] |
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| Chemical and physical data | |
| Formula | C20H25N3O |
| Molar mass | 323.440 g·mol−1 |
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MiPLA, also known asN-methyl-N-isopropyllysergamide or aslysergic acid methylisopropylamide, is apsychedelic drug of thelysergamide family related tolysergic acid diethylamide (LSD).[5][1] It is takenorally.[1][2] The drug is astructural isomer of LSD in which theN,N-diethyl groups have been replaced withN-methyl andN-isopropyl groups.[5][1][6] It is only somewhat lesspotent than LSD as a psychedelic.[1][2] MiPLA has been encountered as a noveldesigner drug.[1][7][8][9]
MiPLA has about 33% to 50% of thepotency of LSD in producingpsychedelic effects in humans.[1][2] According toAlexander Shulgin, it produced LSD-like effects at a dose of 180 to 300 μgorally, 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]
MiPLA and itshomologueEiPLA are the only known simpleN,N-dialkyllysergamides that approach the potency of LSD itself.[5] All otherN,N-dialkylanalogues tested, including thedimethyl,dipropyl,methylethyl, and so on, are only around one-tenth as potent as LSD.[10] However, someN-monoalkyllysergamides, such as thesec-butyl andtert-butyl derivatives, were also found to show activity and potency comparable to LSD.[11] In addition,iPLA, theN-monoisopropyl derivative, is only slightly weaker than MiPLA.[12][13]
MiPLA has been found to interact withserotonin receptors, including acting as anagonist of theserotonin5-HT2A receptor.[14][15][5][13][1][16][17][18][19] It also interacts with thedopamineD1 andD2 receptors.[17][16] The drug fully substitutes forLSD in rodentdrug discrimination tests with only slightly lowerpotency than LSD.[13][5][1][20] In addition, MiPLA produces thehead-twitch response, a behavioral proxy ofpsychedelic 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 asEcPLA.[1]
MiPLA, also known asN-methyl-N-isopropyllysergamide or as lysergic acid methylisopropylamide, is asubstituted lysergamide and astructural isomer oflysergic acid diethylamide (LSD;N,N-diethyllysergamide), with thealkyl groups on theamidenitrogen having been subjected to amethylene shuffle.[6]
Thechemical synthesis of MiPLA has been described.[11][9]
Analogues of MiPLA includeiPLA,EiPLA,EPLA,EcPLA,DiPLA,LSB, andLSP, among others.[14] Theesterderivatives1P-MiPLA and1cP-MiPLA are thought to beprodrugs of MiPLA.[6][21][22]
MiPLA was originally discovered and described byAlbert Hofmann atSandoz during the originalstructure–activity research into LSD, withEli Lilly and Company filing apatent in 1956 and it being published in 1961.[11] It was subsequently investigated in more detail by the team led byDavid E. Nichols atPurdue University in the 1990s.[1][13][5] The main use for this drug has been in studies of the binding site at theserotonin5-HT2A receptor through which LSD produces itshallucinogenic effects.[12] MiPLA was first encountered as a noveldesigner drug by 2018.[1][7][8][9]
MiPLA is technically not illegal inAustria but it may fall in the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich) as an analogue of LSD.[citation needed]
MiPLA is controlled inGermany 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]
MiPLA can be considered a controlled substance inSwitzerland as a defined derivative of Lysergic Acid under Verzeichnis E point 263. It is legal when used for scientific or industrial use.[26]
MiPLA is a controlled substance in theUnited Kingdom via thePsychoactive Substances Act 2016.[citation needed]
MiPLA is not scheduled in theUnited States but may be considered to be an analogue of LSD, which would make it illegal to possess for human consumption under theFederal Analogue Act.[citation needed] However, it may be a Schedule I controlled substance in the United States due to being askeletal isomer[6] of LSD.[citation needed]
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) [...]
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