A diketopiperazine metabolite
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Product Categories

Product Type

Biochemicals
Natural Products
Microbial Metabolites

Research Area

Echinulin

Item No. 22711

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,6S)-3-[[2-(1,1-dimethyl-2-propen-1-yl)-5,7-bis(3-methyl-2-buten-1-yl)-1H-indol-3-yl]methyl]-6-methyl-2,5-piperazinedione
CAS Number
1859-87-6
Molecular Formula
C29H39N3O2
Formula Weight
461.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: soluble
SMILES
C/C(C)=C\CC1=C2C(C(C[C@H]3C(N[C@@H](C)C(N3)=O)=O)=C(C(C)(C)C=C)N2)=CC(C/C=C(C)/C)=C1
InChi Code
InChI=1S/C29H39N3O2/c1-9-29(7,8)26-23(16-24-28(34)30-19(6)27(33)31-24)22-15-20(12-10-17(2)3)14-21(25(22)32-26)13-11-18(4)5/h9-11,14-15,19,24,32H,1,12-13,16H2,2-8H3,(H,30,34)(H,31,33)/t19-,24-/m0/s1
InChi Key
DIKMWTRJIZQJMY-CYFREDJKSA-N
Origin
Fungus/Aspergillus sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    Product Description

    Echinulin is a diketopiperazine metabolite found in fungi that, when administered to rabbits, at a dose of 10 mg/kg, leads to liver and lung damage.1 It has no activity at the δ, κ, or µ-opioid receptors or the cannabinoid CB1 and CB2 receptors.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ali, M., Mohammed, N., Alnaqeeb, M.A., et al. Toxicity of echinulin from Aspergillus chevalieri in rabbits. Toxicol. Lett. 48(3), 235-241 (1989).

    2. Gao, J., Leon, F., Radwan, M.M., et al. Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens. J. Nat. Prod. 74(7), 1636-1639 (2011).