A selective σ2 receptor agonist
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Siramesine (fumarate)

Item No. 21817

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1'-[4-[1-(4-fluorophenyl)-1H-indol-3-yl]butyl]-spiro[isobenzofuran-1(3H),4'-piperidine], 2E-2-butenedioate
CAS Number
163630-79-3
Synonyms
  • Lu 28-179
Molecular Formula
C30H31FN2O • C4H4O4
Formula Weight
570.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.25 mg/ml
λmax
258, 296 nm
SMILES
FC(C=C1)=CC=C1N2C=C(CCCCN3CCC4(C(C=CC=C5)=C5CO4)CC3)C6=C2C=CC=C6.OC(/C=C/C(O)=O)=O
InChi Code
InChI=1S/C30H31FN2O.C4H4O4/c31-25-12-14-26(15-13-25)33-21-23(27-9-2-4-11-29(27)33)7-5-6-18-32-19-16-30(17-20-32)28-10-3-1-8-24(28)22-34-30;5-3(6)1-2-4(7)8/h1-4,8-15,21H,5-7,16-20,22H2;1-2H,(H,5,6)(H,7,8)/b;2-1+
InChi Key
VONJQLKJOYOVBE-WLHGVMLRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

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    10 mg

    $196

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    25 mg

    $437

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    Cayman Chemical
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    Product Description

    Siramesine is an agonist of the sigma-2 (σ2) receptor (IC50 = 0.19 nM).1 It is selective for σ2 over σ1 (IC50 = 17 nM) and related receptors and transporters.1 Siramesine is anxiolytic without inducing sedation or impairing motor coordination in animal studies.1 It is known to induce the death of cancer cells in vitro by destabilizing lysosomes, although it has also been shown to destabilize mitochondria and, with lapatinib (Item No. 11493), induce ferroptosis.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sánchez, C., Arnt, J., Costall, B., et al. The selective σ2-ligand Lu 28-179 has potent anxiolytic-like effects in rodents. J. Pharmacol. Exp. Ther. 283(3), 1323-1332 (1997).

    2. Česen, M.H., Repnik, U., Turk, V., et al. Siramesine triggers cell death through destabilisation of mitochondria, but not lysosomes. Cell Death Dis. 4(10), e818 (2013).

    3. Ma, S., Henson, E.S., Chen, Y., et al. Ferroptosis is induced following siramesine and lapatinib treatment of breast cancer cells. Cell Death Dis. 7(7), e2307 (2016).

    4. Ostenfeld, M.S., Fehrenbacher, N., Høyer-Hansen, M., et al. Effective tumor cell death by σ-2 receptor ligand siramesine involves lysosomal leakage and oxidative stress. Cancer Res. 65(19), 8975-8983 (2005).