View source for Methylisopropyllysergamide

{{drugbox |
| width = 140
| image = MIPLSD.png
| IUPAC_name = (8β)- ''N''- isopropyl- ''N'',6- dimethyl- 9,10- didehydroergoline- 8- carboxamide
| C=20 | H=25 | N=3 | O=1
| molecular_weight = 323.431 g/mol
| ATC_prefix = none
| synonyms = (6a''R'',9''R'')- ''N''-methyl- ''N''-isopropyl- 7-methyl- 4,6,6a,7,8,9- hexahydroindolo- [4,3-''fg''] quinoline- 9- carboxamide;
Lysergic acid methylisopropyl amide
| PubChem = 
| smiles = C4N(C)C1Cc2cnc(ccc3)c2c3C1=CC4C(=O)N(C)C(C)C
| metabolism = 
| excretion = 
| legal_AU = 
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| legal_UK = 
| legal_US = 
| legal_status = 
| routes_of_administration = 
}}

'''Methylisopropyllysergamide''' ('''lysergic acid methylisopropyl amide''', '''MIPLA''') is an analogue of [[LSD]] that was originally discovered by [[Albert Hofmann]] at [[Sandoz]] during the original structure-activity research into LSD. It has subsequently been investigated in more detail by the team led by [[David E. Nichols]] at [[Purdue University]]. Methylisopropyllysergamide is a [[structural isomer]] of LSD, with the alkyl groups on the amide nitrogen having been subjected to a [[methylene shuffle]]. It is the only simple N,N-dialkyl lysergamide that approaches the potency of LSD itself, being around 1/3rd-1/2 the potency of LSD, while all other dialkyl analogues (dimethyl, dipropyl, methylethyl etc) are only around 1/10th as potent as LSD.<ref>Hofmann A. Psychotomimetic Drugs: Chemical and Pharmacological Aspects. ''Acta. Physiol. Pharmacol. Neerlandica''. 1959;8:240-258.</ref> Apart from its lower potency, the hallucinogenic effects of methylisopropyllysergamide are similar to those of LSD itself, and the main use for this drug has been in studies of the binding site at the [[5-HT2A receptor|5-HT<sub>2A</sub>]] [[Receptor (biochemistry)|receptor]] through which LSD exerts most of its pharmacological effects.<ref>David E. Nichols. LSD and Its Lysergamide Cousins. ''The Heffter Review of Psychedelic Research''. 2001;2:80-87.</ref> 

==References==
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{{Hallucinogenic lysergamides}}

[[Category:Psychedelic drugs]]
[[Category:Lysergamides]]


{{hallucinogen-stub}}
[[Category:2Fix]]