Akuammine

Akuammine is an indole alkaloid that has been found in Picralima nitida and has analgesic activity. It selectively binds to the µ- and kappa-opioid receptors over the delta-opioid receptor (Kis = 0.3, 1.68, and 10.4 µM for the human receptors, respectively). Akuammine inhibits forskolin-induced cAMP production in HEK293 cells expressing human µ- or kappa-opioid receptors (IC50s = 2.6 and 0.073 µM, respectively). It increases the latency to withdrawal in the tail-flick or hot plate test in mice when administered at a dose of 60 mg/kg.Formal Name: (2S,3E,7aS,12aS,12bS,15R)-3-ethylidene-1,3,4,6,7,12b-hexahydro-9-hydroxy-12-methyl-2H,12H-12a,2,7a-(epoxyethanylylidene)indolo[2,3-a]quinolizine-15-carboxylic acid, methyl ester. CAS Number: 3512-87-6. Synonyms: (-)-Akuammine, Vincamajoridine. Molecular Formula: C22H26N2O4. Formula Weight: 382.5. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 2 mg/ml, DMSO: 1 mg/ml, Ethanol: insol, PBS (pH 7.2): insol. SMILES: COC([C@@]12[C@]34[C@](N(C5=CC=C(O)C=C54)C)(OC2)[C@](N(C/6)CC3)([H])C[C@H]1C6=C/C)=O. InChi Code: InChI=1S/C22H26N2O4/c1-4-13-11-24-8-7-21-16-9-14(25)5-6-17(16)23(2)22(21)18(24)10-15(13)20(21,12-28-22)19(26)27-3/h4-6,9,15,18,25H,7-8,10-12H2,1-3H3/b13-4-/t15-,18-,20-,21-,22+/m0/s1. InChi Key: YILKZADAWNUTTB-QLWRWLBVSA-N. Origin: Plant/Picralima nitida.