An inhibitor of monoamine transporters and OCTs
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Decynium-22

Item No. 29494

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-ethyl-2-[(1-ethyl-2(1H)-quinolinylidene)methyl]-quinolinium, monoiodide
CAS Number
977-96-8
Synonyms
  • 1,1′-Diethyl-2,2′-Cyanine
Molecular Formula
C23H23N2 • I
Formula Weight
454.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 1 mg/mlDMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
226, 491, 524 nm
SMILES
CCN(C1=CC=CC=C1C=C/2)C2=C\C3=[N+](CC)C4=C(C=CC=C4)C=C3.[I-]
InChi Code
InChI=1S/C23H23N2.HI/c1-3-24-20(15-13-18-9-5-7-11-22(18)24)17-21-16-14-19-10-6-8-12-23(19)25(21)4-2;/h5-17H,3-4H2,1-2H3;1H/q+1;/p-1
InChi Key
GMYRVMSXMHEDTL-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $54

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    500 mg

    $102

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    1 g

    $190

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    Product Description

    Decynium-22 is an inhibitor of monoamine transporters and organic cation transporters (OCTs).1 It inhibits the plasma membrane monoamine, serotonin (5-HT), norepinephrine, and dopamine monoamine transporters (IC50s = 1.1, 7.9, 30, and 12.9 µM, respectively), and OCT2 and OCT3 (IC50s = 10 and 0.2 µM, respectively) in radioligand binding assays. Decynium-22 also inhibits binding of the α1-adrenergic receptor antagonist prazosin (Item No. 15023) in mouse hippocampal homogenates (IC50 = 60 nM).2 It decreases the time stress-sensitive Wistar Kyoto, but not stress-resistant Long-Evans, rats spend immobile in the forced swim test, indicating antidepressant-like activity, when administered at doses of 1 and 10 µg/kg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fraser-Spears, R., Krause-Heuer, A.M., Basiouny, M., et al. Comparative analysis of novel decynium-22 analogs to inhibit transport by the low-affinity, high-capacity monoamine transporters, organic cation transporters 2 and 3, and plasma membrane monoamine transporter. Eur. J. Pharmacol. 842, 351-364 (2019).

    2. Krause-Heuer, A.M., Fraser-Spears, R., Dobrowolski, J.C., et al. Evaluation of the antidepressant therapeutic potential of isocyanine and pseudoisocyanine analogues of the organic cation decynium-22. Eur. J. Med. Chem. 137, 476-487 (2017).

    3. Marcinkiewcz, C.A., and Devine, D.P. Modulation of OCT3 expression by stress, and antidepressant-like activity of decynium-22 in an animal model of depression. Pharmacol. Biochem. Behav. 131, 33-41 (2015).