Isopilocarpine
Isopilocarpine is a synthetic alkaloid analog of Pilocarpine, featuring a 3a,8a-dihydroxy-2-oxo-2,3,3a,4,5,6,7,8-octahydro-1H-quinolin-1-ium core with a substituted methylamino group at position 2. Its stereochemistry and hydroxyl positioning differ from the parent compound, altering its cholinergic activity profile. The molecule exhibits a zwitterionic character due to the quaternary ammonium and adjacent carboxylate functionalities. Structurally, it serves as a key intermediate in the synthesis of Pilocarpine derivatives, enabling stereocontrolled modifications for pharmacokinetic optimization.
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IUPAC Name
(3R,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
📝 Synonyms
(+)-Isopilocarpine
isopilocarpine
3-Isopilocarpine
531-35-1
J9UV7D2OI9
CHEBI:39458
DTXSID701316166
(3R,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydrofuran-2(3H)-one
(3R,4R)-3-ETHYL-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)DIHYDROFURAN-2(3H)-ONE
RefChem:905468
🔬 Chemical Identifiers
CC[C@@H]1[C@H](COC1=O)CC2=CN=CN2C
InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10+/m0/s1
QCHFTSOMWOSFHM-WCBMZHEXSA-N
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