A dopamine D2 receptor antagonist
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L-741,626

Item No. 22354

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(4-chlorophenyl)-1-(1H-indol-3-ylmethyl)-4-piperidinol
CAS Number
81226-60-0
Molecular Formula
C20H21ClN2O
Formula Weight
340.9
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 33 mg/mlDMSO: 33 mg/mlEthanol: 33 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
221 nm
SMILES
ClC1=CC=C(C2(O)CCN(CC3=CNC4=C3C=CC=C4)CC2)C=C1
InChi Code
InChI=1S/C20H21ClN2O/c21-17-7-5-16(6-8-17)20(24)9-11-23(12-10-20)14-15-13-22-19-4-2-1-3-18(15)19/h1-8,13,22,24H,9-12,14H2
InChi Key
LLBLNMUONVVVPG-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $75

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    10 mg

    $128

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    25 mg

    $295

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    Product Description

    L-741,626 is an antagonist of the dopamine D2 receptor (Kis = 2.4, 100, and 220 nM for human D2, D3, and D4, respectively, in a radioligand displacement assay).1 L-741,626 is selective for D2 receptors (Ki = 3.98 nM) over serotonin receptors (Kis ≤ 316.2 nM for human 5-HT1A, 5-HT1B, 5-HT1D, 5-HT2A, 5-HT2B, 5-HT2C, and 5-HT3).2 In a functional assay, L-741,626 inhibits quinpirole-stimulated mitogenesis with EC50 values of 4.46 and 90.4 nM in CHO cells transfected with human D2long and D3 receptors, respectively.3 L-741,626 (3 μM) reversibly blocks D2-mediated currents in Xenopus oocytes via G protein-gated inwardly rectifying K+ (GIRK) channels.4 In models of potential antipsychotic activity, L-741,626 inhibits apomorphine-induced climbing behavior in mice (ID50 = 0.3 mg/kg, s.c.) and the conditioned avoidance response (CAR) in rats (ID50 = 6.1 mg/kg, s.c.).5 L-741,626 evokes a catalepsy response (AD50 = 7.0 mg/kg, s.c.) and blocks gnawing induced by methylphenidate (Item No. 11639; ID50 = 2.4 mg/kg, s.c.) in rat models of potential extrapyramidal activity.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kulagowski, J.J., Broughton, H.B., Curtis, N.R., et al. 3-((4-(4-Chlorophenyl)piperazin-1-yl)-methyl)-1H-pyrrolo[2,3-b]pyridine: An antagonist with high affinity and selectivity for the human dopamine D4 receptor. J. Med. Chem. 39(10), 1941-1942 (1996).

    2. Millan, M.J., Gobert, A., Newman-Tancredi, A., et al. S33084, a novel, potent, selective, and competitive antagonist at dopamine D3-receptors: I. Receptorial, electrophysiological and neurochemical profile compared with GR218,231 and L741,626. J. Pharmacol. Exp. Ther. 293(3), 1048-1062 (2000).

    3. Grundt, P., Husband, S.L., Luedtke, R.R., et al. Analogues of the dopamine D2 receptor antagonist L741,626: Binding, function, and SAR. Bioorg. Med. Chem. Lett. 17(3), 745-749 (2007).

    4. Pillai, G., Brown, N.A., McAllister, G., et al. Human D2 and D4 dopamine receptors couple through βγ G-protein subunits to inwardly rectifying K+ channels (GIRK1) in a Xenopus oocyte expression system: selective antagonism by L-741,626 and L-745,870 respectively. Neuropharmacology 37(8), 983-987 (1998).

    5. Millan, M.J., Dekeyne, A., Rivet, J.M., et al. S33084, a novel, potent, selective, and competitive antagonist at dopamine D3-receptors: II. Functional and behavioral profile compared with GR218,231 and L741,626. J. Pharmacol. Exp. Ther. 293(3), 1063-1073 (2000).