88360-87-6

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88360-87-6 Structure

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

Safety Data	Back Directory
[Symbol(GHS) ] GHS07
[Signal word ] Warning
[Hazard statements ] H302+H312+H332
[Precautionary statements ] P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P321-P330-P362+P364-P501
[Toxicity] LD50 intraperitoneal in mouse: > 200mg/kg

Hazard Information	Back Directory
[Description] Amauromine is a neutral antagonist of the cannabinoid (CB) receptor CB₁ that is selective for CB₁ (K_i = 178 nM; K_b = 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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