| Identification | Back Directory | [Name]
amauromine | [CAS]
88360-87-6 | [Synonyms]
WF-6237
FR-900220
amauromine
Antibiotic FR-900220
4'',5'':1',5']dipyrrolo[2,3-b:2',3'-b']diindole-7,15(5H,7aH)-dione
(5aS,7aS,8aR,13aS,15aS,16aR)-8a,16a-Bis(1,1-dimethyl-2-propen-1-yl)-5a,8,8a,13,13a,15a,16,16a-octahydro-pyrazino[1'',2'':1,5
(5aS)-8aα,16aα-Bis(1,1-dimethyl-2-propenyl)-5aα,8,8a,13,13aα,15aβ,16,16a-octahydropyrazino[1'',2'':1,5:4'',5'':1',5']dipyrrolo[2,3-b:2',3'-b']diindole-7,15(5H,7aβH)-dione | [Molecular Formula]
C32H36N4O2 | [MDL Number]
MFCD01939909 | [MOL File]
88360-87-6.mol | [Molecular Weight]
508.662 |
| Chemical Properties | Back Directory | [Boiling point ]
689.9±55.0 °C(Predicted) | [density ]
1.28±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble | [form ]
A solid | [pka]
3.26±0.60(Predicted) | [color ]
Brown |
| Hazard Information | Back Directory | [Description]
Amauromine is a neutral antagonist of the cannabinoid (CB) receptor CB1 that is selective for CB1 (Ki = 178 nM; Kb = 66.6 nM) over CB2, with no activity at CB2 receptors at concentrations up to 10 μM. It is also an antagonist of GPR18 (IC50 = 3.74 μM). Amauromine has vasodilatory activity. | [Uses]
Amauromine is a CB1 and Calcium Channel antagonist. | [IC 50]
CB1: 178 nM (Ki); CB1: 66.6 nM (Kb) | [storage]
Store at -20°C | [References]
[1] MAHMOUD FAHMI ELSEBAI. Identification of a Potent and Selective Cannabinoid CB1 Receptor Antagonist from Auxarthron reticulatum[J]. ACS Medicinal Chemistry Letters, 2011, 2 11: 866-869. DOI: 10.1021/ml200183z
[2] MAMONA NAZIR. GPR18 Inhibiting Amauromine and the Novel Triterpene Glycoside Auxarthonoside from the Sponge-Derived Fungus Auxarthron reticulatum.[J]. Planta medica, 2015, 81 12-13: 1141-1145. DOI: 10.1055/s-0035-1545979
[3] SHIGEHIRO TAKASE. Structure of amauromine, a new alkaloid with vasodilating activity produced by amauroascus sp.[J]. Tetrahedron Letters, 1984, 25 41: Pages 4673-4676. DOI: 10.1016/s0040-4039(01)91230-4 |
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