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88360-87-6

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88360-87-6 Structure

88360-87-6 Structure
IdentificationBack 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 PropertiesBack 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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
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 InformationBack 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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