Methylisopropyllysergamide (MIPLA), also known as lysergic acid methylisopropylamide, is an analogue of
LSD
Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity. I ...
that was originally discovered by
Albert Hofmann
Albert Hofmann (11 January 1906 – 29 April 2008) was a Swiss chemist known for being the first to synthesize, ingest, and learn of the psychedelic effects of lysergic acid diethylamide (LSD). Hofmann's team also isolated, named and synthesi ...
at
Sandoz
Sandoz Group AG is a Swiss company that focuses on generic pharmaceuticals and biosimilars. Prior to October 2023, it was part of a division of Novartis that was established in 2003, when Novartis united all of its generics businesses under the ...
during the original structure-activity research into LSD. It has subsequently been investigated in more detail by the team led by
David E. Nichols
David Earl Nichols (born December 23, 1944, Covington, Kentucky) is an American pharmacologist and medicinal chemist.
Previously the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worke ...
at
Purdue University
Purdue University is a Public university#United States, public Land-grant university, land-grant research university in West Lafayette, Indiana, United States, and the flagship campus of the Purdue University system. The university was founded ...
.
The drug is a
structural isomer
In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...
of LSD, with the alkyl groups on the amide nitrogen having been subjected to a
methylene shuffle. MIPLA and its ethylisopropyl homologue
EIPLA are the only simple N,N-dialkyl lysergamides that approach the potency of LSD itself, being around 1/3-1/2 the potency of LSD,
while all other dialkyl analogues tested (dimethyl, dipropyl, methylethyl etc.) are only around 1/10 as potent as LSD,
although some N-monoalkyl lysergamides such as the
''sec''-butyl and ''t''-butyl derivatives were also found to show an activity profile and potency comparable to LSD, and the mono-isopropyl derivative is only slightly weaker than MIPLA.
Apart from its lower potency, the hallucinogenic effects of MIPLA 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
Receptor may refer to:
* Sensory receptor, in physiology, any neurite structure that, on receiving environmental stimuli, produces an informative nerve impulse
*Receptor (biochemistry), in biochemistry, a protein molecule that receives and respond ...
through which LSD exerts most of its pharmacological effects.
See also
*
Ethylpropyllysergamide
''N''-Ethyl-''N''-propyllysergamide (EPLA), also known as lysergic acid ethylpropylamide (LEP or LEP-57), is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD). It is the analogue of LSD in which the amide g ...
(EPLA)
*
Lysergic acid 2-butyl amide
Lysergic acid 2-butyl amide (LSB), also known as 2-butyllysergamide, is an analogue of LSD originally developed by Richard Pioch at Eli Lilly in the 1950s, but mostly publicised through research conducted by the team led by David E. Nichols at P ...
*
Lysergic acid 3-pentyl amide
References
Psychedelic lysergamides
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