Irreversible inhibitor of VMAT1 and VMAT2
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Reserpine

Item No. 16474

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester
CAS Number
50-55-5
Synonyms
  • NSC 59272
  • NSC 237659
  • Rausedil
Molecular Formula
C33H40N2O9
Formula Weight
608.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:5): 0.1 mg/mlDMSO: 10 mg/ml
λmax
216, 267, 296 nm
SMILES
COC1=CC(C(O[C@@H]2C[C@@](CN(CCC3=C4NC5=C3C=CC(OC)=C5)[C@]4([H])C6)([H])[C@@]6([H])[C@H](C(OC)=O)[C@H]2OC)=O)=CC(OC)=C1OC
InChi Code
InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
InChi Key
QEVHRUUCFGRFIF-MDEJGZGSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

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    5 g

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    Product Description

    Reserpine is an alkaloid isolated from dried roots of R. serpentine, which is used in traditional Indian medicine. Reserpine irreversibly inhibits both human isoforms of vesicular monoamine transporter, VMAT1 and VMAT2 (Kis = 34 and 12 nM, respectively).1,2 As this leads to metabolism of monoamines, reserpine is used to experimentally deplete monoamines in animals.3,4,5 Reserpine also inhibits the multidrug resistance protein P-glycoprotein (IC50 = 0.5 µM).6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schuldiner, S., Liu, Y., and Edwards, R.H. Reserpine binding to a vesicular amine transporter expressed in Chinese hamster ovary fibroblasts. The Journal of Biological Chemisty 268(1), 29-34 (1993).

    2. Erickson, J.D., Schäfer, M.K.H., Bonner, T.I., et al. Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter. Proc. Natl. Acad. Sci. USA 93(10), 5166-5171 (1996).

    3. Hu, X.T., Wachtel, S.R., Galloway, M.P., et al. Lesions of the nigrostriatal dopamine projection increase the inhibitory effects of D1 and D2 dopamine agonists on caudate-putamen neurons and relieve D2 receptors from the necessity of D1 receptor stimulation. J. Neurosci. 10(7), 2318-2329 (1990).

    4. Stanwood, G.D., Lucki, I., and McGonigle, P. Differential regulation of dopamine D2 and D3 receptors by chronic drug treatments. J. Pharmacol. Exp. Ther. 295(3), 1232-1240 (2000).

    5. Matsumoto, K., Mizowaki, M., Suchitra, T., et al. Central antinociceptive effects of mitragynine in mice: Contribution of descending noradrenergic and serotonergic systems. Eur. J. Pharmacol. 317(1), 75-81 (1996).

    6. Wang, E.j., Lew, K., Barecki, M., et al. Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem. Res. Toxicol. 14(12), 1596-1603 (2001).