| Identification | Back Directory | [Name]
akuammine | [CAS]
3512-87-6 | [Synonyms]
akuammine
Vincamajoridine
(2S,3E,7aα,12aα,12bβ,15R)-3-Ethylidene-1,3,4,6,7,12b-hexahydro-9-hydroxy-12-methyl-2H,12H-12a,2,7a-(epoxyethanylidene)indolo[2,3-a]quinolizine-15-carboxylic acid methyl ester
2H,12H-12a,2,7a-(Epoxyethanylylidene)indolo[2,3-a]quinolizine-15-carboxylic acid, 3-ethylidene-1,3,4,6,7,12b-hexahydro-9-hydroxy-12-methyl-, methyl ester, (2S,3E,7aS,12aS,12bS,15R)- | [Molecular Formula]
C22H26N2O4 | [MOL File]
3512-87-6.mol | [Molecular Weight]
382.46 |
| Chemical Properties | Back Directory | [Melting point ]
316 °C | [alpha ]
D16 -105.3° (c = 1.31 in pyridine) | [Boiling point ]
564.0±50.0 °C(Predicted) | [density ]
1.40±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMF: 2 mg/ml,DMSO: 1 mg/ml,Ethanol: insol,PBS (pH 7.2): insol | [form ]
A crystalline solid | [pka]
7.5(at 25℃) | [optical activity]
-73.420 (c 0.8716, CHCl3) |
| Hazard Information | Back Directory | [Uses]
Akuammine is an indole alkaloid that has been found in Picralima nitida and has analgesic activity. It selectively binds to the μ- and κ-opioid receptors over the δ-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 κ-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. | [storage]
-20°C | [References]
[1] Creed, et al. Isolation and pharmacological characterization of six opioidergic Picralima nitida alkaloids. J. Nat. Prod. 84(1), 71-80 (2021). |
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