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Lysergic acid 2,4-dimethylazetidide: Wikis

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Lysergic acid 2,4-dimethylazetidide
Systematic (IUPAC) name
(8β)-8- {[(2S,4S)- 2,4-dimethylazetidin- 1-yl] carbonyl}- 6-methyl- 9,10- didehydroergoline
Identifiers
CAS number  ?
ATC code  ?
PubChem 10472143
Chemical data
Formula C 21H25N3O 
Mol. mass 335.442 g/mol
SMILES eMolecules & PubChem
Synonyms Lysergic acid 2,4-dimethylazetidine
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

Lysergic acid 2,4-dimethylazetidide (LA-SS-Az) is an analogue of LSD developed by the team led by David E. Nichols at Purdue University. It was developed as a rigid analogue of LSD with the diethylamide group constrained into an azetidine ring in order to map the binding site at the 5-HT2A receptor. There are three possible stereoisomers around the azetidine ring, with the (S,S)-(+) isomer being the most active, slightly more potent than LSD itself in drug discrimination tests using trained rats.[1]

References

  1. ^ Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM. Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). Journal of Medicinal Chemistry. 2002 Sep 12;45(19):4344-9. PMID 12213075
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