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Methylisopropyllysergamide: Wikis

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Methylisopropyllysergamide
Systematic (IUPAC) name
(8β)- N- isopropyl- N,6- dimethyl- 9,10- didehydroergoline- 8- carboxamide
Identifiers
CAS number  ?
ATC code none
PubChem  ?
Chemical data
Formula C 20H25N3O 
Mol. mass 323.431 g/mol
SMILES eMolecules & PubChem
Synonyms (6aR,9R)- N-methyl- N-isopropyl- 7-methyl- 4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9- carboxamide;

Lysergic acid methylisopropyl amide

Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
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Therapeutic considerations
Pregnancy cat.  ?
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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.[1] 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 through which LSD exerts most of its pharmacological effects.[2]

References

  1. ^ Hofmann A. Psychotomimetic Drugs: Chemical and Pharmacological Aspects. Acta. Physiol. Pharmacol. Neerlandica. 1959;8:240-258.
  2. ^ David E. Nichols. LSD and Its Lysergamide Cousins. The Heffter Review of Psychedelic Research. 2001;2:80-87.
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