An alkaloid with diverse biological activities
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Isomer(s)
21100Mesembrine
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(±)-Mesembrenol

Item No. 40470

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6S)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,3a,6,7,7a-hexahydro-1H-indol-6-ol
Molecular Formula
C17H23NO3
Formula Weight
289.4
Purity
≥98%
Formulation (Request formulation change)
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: Slightly soluble: 0.1-1 mg/ml
SMILES
COC1=C(OC)C=C(C2(CCN3C)C3([H])C[C@H](O)C=C2)C=C1
InChi Code
InChI=1S/C17H23NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-7,10,13,16,19H,8-9,11H2,1-3H3/t13-,16?,17?/m1/s1
InChi Key
PQBHZMSTECYZLH-NVPAJSRCSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $396

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    1 mg

    $752

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    Product Description

    (±)-Mesembrenol is an alkaloid that has been found in S. tortuosum and has diverse biological activities.1 It binds to the serotonin transporter (SERT) with a Ki value of 62 nM. (±)-Mesembrenol reduces single-shock- and theta burst-stimulated population spike amplitudes in rat hippocampal slices.2 It also reduces population spike amplitudes increased by the AMPA agonist (S)-(–)-5-fluorowillardiine (Item No. 37372) when used at a concentration of 0.035 µM. (±)-Mesembrenol (10-50 µM) reduces anxiety-like behavior in zebrafish larvae in a light-dark challenge.3 As one of the major mesembrine-type alkaloids found in certain chemotypes of S. tortuosum, (±)-mesembrenol can be used as a marker compound in the quality control of S. tortuosum raw materials and finished products.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Harvey, A.L., Young, L.C., Viljoen, A.M., et al. Pharmacological actions of the South African medicinal and functional food plant Sceletium tortuosum and its principal alkaloids. J. Ethnopharmacol. 137(3), 1124-1129 (2011).

    2. Dimpfel, W., Franklin, R., Gericke, N., et al. Effect of Zembrin® and four of its alkaloid constituents on electric excitability of the rat hippocampus. J. Ethnopharmacol. 223, 135-141 (2018).

    3. Maphanga, V.B., Skalicka-Wozniak, K., Budzynska, B., et al. Mesembryanthemum tortuosum L. alkaloids modify anxiety-like behaviour in a zebrafish model. J. Ethnopharmacol. 290, 115068 (2022).

    4. Shikanga, E.A., Viljoen, A.M., Combrinck, S., et al. The chemotypic variation of Sceletium tortuosum alkaloids and commercial product formulations. Biochem. Syst. Ecol. 44, 364-373 (2012).