Methylisopropyllysergamide

Methylisopropyllysergamide
Clinical data
Other names	MIPLA; Lysergic acid methylisopropylamide
ATC code	None;
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act; US: Schedule I (isomer of LSD); Illegal in France;
Identifiers
	IUPAC name (8β)-N-Isopropyl-N,6-dimethyl-9,10-didehydroergoline-8-carboxamide;
CAS Number	100768-08-9 ;
PubChem CID	57507938;
UNII	AC6WQQ5Y4B;
Chemical and physical data
Formula	C20H25N3O
Molar mass	323.440 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C4N(C)C1Cc2c[nH]c(ccc3)c2c3C1=CC4C(=O)N(C)C(C)C;
	InChI 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)

Methylisopropyllysergamide (MIPLA), also known as lysergic acid methylisopropylamide, 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.

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The drug is a structural isomer 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,^[2] while all other dialkyl analogues tested (dimethyl, dipropyl, methylethyl etc.) are only around 1/10 as potent as LSD,^[3] 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,^[4] 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-HT_2A receptor through which LSD exerts most of its pharmacological effects.^[5]

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Methylisopropyllysergamide

See also

References

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