An alkaloid with diverse biological activities
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Scopolamine

Item No. 40307

Technical Information
Formal Name
αS-(hydroxymethyl)-benzeneacetic acid, (1α,2β,4β,5α,7β)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester
CAS Number
51-34-3
Synonyms
  • Hyoscine
Molecular Formula
C17H21NO4
Formula Weight
Purity
≥98%
Formulation
A low-melting solid
DMSO: Soluble: ≥10 mg/mlEthanol: Soluble: ≥10 mg/mlPBS (pH 7.2): Sparingly soluble: 1-10 mg/ml
SMILES
O=C(O[C@H]1C[C@H](N2C)[C@@H]3O[C@@H]3[C@H]2C1)[C@H](CO)C4=CC=CC=C4
InChi Code
InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1
InChi Key
STECJAGHUSJQJN-FWXGHANASA-N
Origin
Plant/Datura
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Scopolamine is an alkaloid that has been found in D. stramonium and has diverse biological activities.1,2,3,4,5,6 It is an antagonist of muscarinic acetylcholine receptors (mAChRs; Kis = 0.19, 1.41, and 0.18 nM for the rat M1, M2, and M3 receptors, respectively).2 Scopolamine reduces acetylcholine-induced contractions in isolated guinea pig ileum (IC50 = 8.1 nM).3 It inhibits tremors induced by the mAChR agonist oxotremorine (Item No. 35707) in mice (ED50 = 0.23 mg/kg). Scopolamine increases fine motor activity counts and ambulatory activity in rats in a home-cage activity test (ED50 = 0.12 mg/kg for both).4 It has been used to induce learning deficiencies or amnesia in animal models.5,6 Formulations containing scopolamine have been used in the treatment of motion sickness and postoperative nausea and vomiting. This product is also available as an analytical reference standard (Item No. 14108).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ma, L., Gu, R., Tang, L., et alImportant poisonous plants in Tibetan ethnomedicine. Toxins (Basel) 7(1), 138-155 (2015).

    2. Lazareno, S., Buckley, N.J., and Roberts, F.F. Characterization of muscarinic M4 binding sites in rabbit lung, chicken heart, and NG108-15 cell. Mol. Pharmacol. 38(6), 805-815 (1990).

    3. Fjalland, B., Christensen, A.V., and Hyttel, J. Peripheral and central muscarinic receptor affinity of psychotropic drugs. Naunyn. Schmiedebergs. Arch. Pharmacol. 301(1), 5-9 (1977).

    4. Sipos, M.L., Burchnell, V., and Galbicka, G. Dose-response curves and time-course effects of selected anticholinergics on locomotor activity in rats. Psychopharmacology 147(3), 250-256 (1999).

    5. Bratt, A.M., Kelly, M.E., Domeney, A.M., et alAcute and chronic arecoline: Effects on a scopolamine-induced deficit in complex maze learning. Pharmacol. Biochem. Behav. 53(3), 713-721 (1996).

    6. Ano, Y., Kutsukake, T., Sasaki, T., et alIdentification of a novel peptide from β-casein that enhances spatial and object recognition memory in mice. J. Agric. Food Chem. 67(29), 8160-8167 (2019).