A CB1 receptor neutral antagonist
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Amauromine

Item No. 23886

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(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;4'',5'':1',5']dipyrrolo[2,3-b:2',3'-b']diindole-7,15(5H,7aH)-dione
CAS Number
88360-87-6
Molecular Formula
C32H36N4O2
Formula Weight
508.7
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
C=CC(C)(C)[C@]1([C@@]2([H])NC3=C1C=CC=C3)C[C@]4([H])N2C([C@@](C[C@]5(C(C)(C)C=C)[C@@]6([H])NC7=C5C=CC=C7)([H])N6C4=O)=O
InChi Code
InChI=1S/C32H36N4O2/c1-7-29(3,4)31-17-23-25(37)36-24(26(38)35(23)27(31)33-21-15-11-9-13-19(21)31)18-32(30(5,6)8-2)20-14-10-12-16-22(20)34-28(32)36/h7-16,23-24,27-28,33-34H,1-2,17-18H2,3-6H3/t23-,24-,27-,28-,31+,32+/m0/s1
InChi Key
VKEAHNPKYMHYJJ-CBYNOBLXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    250 µg

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    Product 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.1 It is also an antagonist of GPR18 (IC50 = 3.74 µM).2 Amauromine has vasodilatory activity.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Elsebai, M.F., Rempel, V., Schnakenburg, G., et al. Identification of a potent and selective cannabinoid CB1 receptor antagonist from Auxarthron reticulatum. ACS Med. Chem. Lett. 2(11), 866-869 (2011).

    2. Nazir, M., Harms, H., Loef, I., et al. GPR18 inhibiting amauromine and the novel triterpene glycoside auxarthonoside from the sponge-derived fungus Auxarthron reticulatum. Planta. Med. 81(12-13), 1141-1145 (2015).

    3. Takase, S., Kawai, Y., Uchida, I., et al. Structure of amauromine, a new alkaloid with vasodilating activity produced by Amauroascus. sp. Tetrahedron Lett. 25(41), 4673-4676 (1984).