A dopamine receptor antagonist and 5-HT1A partial agonist
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Isomer(s)
35140Scoulerine
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(–)-Stepholidine

Item No. 26612

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(13aS)-5,8,13,13a-tetrahydro-3,9-dimethoxy-6H-dibenzo[a,g]quinolizine-2,10-diol
CAS Number
16562-13-3
Molecular Formula
C19H21NO4
Formula Weight
327.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/mlDMSO:PBS (pH 7.2) (1:6): 0.14 mg/mlEthanol: 1.1 mg/ml
λmax
242, 279 nm
SMILES
OC1=CC2=C(C=C1OC)CCN3CC4=C(OC)C(O)=CC=C4C[C@]32[H]
InChi Code
InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
InChi Key
JKPISQIIWUONPB-HNNXBMFYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $359

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    1 mg

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    5 mg

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    Product Description

    (–)-Stepholidine is a dopamine receptor antagonist and a partial agonist of the serotonin (5-HT) receptor subtype 5-HT1A.1,2,3 (–)-Stepholidine binds to dopamine D1, D2, D3, D4, and D5 receptors (Kis = 5.1, 11.6, 24, 1,450, and 5.8 nM, respectively) as well as 5-HT1A, 5-HT2B, α2C-adrenergic receptors (α2C-ARs), and sigma-2 (σ2) receptors in a radioligand binding assay (Kis = 143, 226, 215, and 53 nM, respectively).1 It inhibits dopamine-induced cAMP accumulation in HEK293 cells expressing dopamine D1, D2, and D5 receptors with IC50 values of 20.5, 128, and 27 nM, respectively. (–)-Stepholidine inhibits forskolin-induced cAMP production in CHO cells expressing rat 5-HT1A receptors (EC50 = 1.2 μM).2 In vivo, (–)-stepholidine (1 mg/kg, i.v.) increases dopamine neuron firing rates, the number of spikes in bursts, and the amplitude of slow oscillations by 20, 155, and 126%, respectively, in the rat ventral tegmental area (VTA), effects that can be blocked by the 5-HT1A antagonist WAY-100635 (Item No. 14599).3 Pretreatment with (–)-stepholidine inhibits amphetamine- and phencyclidine-induced locomotor activity in rats (ED50s = 2.4 and 6.5 mg/kg, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Meade, J.A., Free, R.B., Miller, N.R., et al. (−)-Stepholidine is a potent pan-dopamine receptor antagonist of both G protein- and β-arrestin-mediated signaling. Psychopharmacology 232(5), 917-630 (2015).

    2. Mo, J., Zhang, H., Yu, L.-P., et al. L-stepholidine reduced L-DOPA-induced dyskinesia in 6-OHDA-lesioned rat model of Parkinson’s disease. Neurobiol. Aging 31(6), 926-936 (2010).

    3. Gao, M., Chu, H.-Y., Jin, G.-Z., et al. l-Stepholidine-induced excitation of dopamine neurons in rat ventral tegmental area is associated with its 5-HT1A receptor partial agonistic activity. Synapse 65(5), 379-387 (2011).

    4. Natesan, S., Reckless, G.E., Barlow, K.B.L., et al. The antipsychotic potential of l-stepholidine--a naturally occurring dopamine receptor D1 agonist and D2 antagonist. Psychopharmacology 199(2), 275-289 (2008).