An indole alkaloid with antinociceptive activity
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Gelsenicine

Item No. 46552

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,3′R,3′aS,6′R,8′aS)-2′-ethyl-3′a,4′,8′,8′a-tetrahydro-1-methoxy-spiro[3H-indole-3,7′(6′H)-[3,6]methano[3H]oxepino[4,3-b]pyrrol]-2(1H)-one
CAS Number
82354-38-9
Molecular Formula
C19H22N2O3
Formula Weight
326.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Ethanol: Sparingly soluble: 1-10 mg/ml
SMILES
O=C1[C@]2([C@@](OC3)([H])C[C@]4([H])[C@@]3([H])[C@](N=C4CC)([H])C2)C5=CC=CC=C5N1OC
InChi Code
InChI=1S/C19H22N2O3/c1-3-14-11-8-17-19(9-15(20-14)12(11)10-24-17)13-6-4-5-7-16(13)21(23-2)18(19)22/h4-7,11-12,15,17H,3,8-10H2,1-2H3/t11-,12+,15+,17-,19+/m1/s1
InChi Key
BIGABVPVCRHEES-NWPJSNQLSA-N
Origin
Plant/Gelsemium elegans
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

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    10 mg

    $270

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    25 mg

    $551

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    Product Description

    Gelsenicine is an indole alkaloid that has been found in G. elegans and has antinociceptive activity.1,2,3 It reduces acetic acid-induced writhing and formalin-induced paw licking in mice (ED50s = 10.4 and 7.4 µg/kg, respectively) and inhibits chronic constriction injury-induced thermal hyperalgesia in a mouse model of neuropathic pain (ED50 = 9.8 µg/kg).2 Gelsenicine is lethal to rats (LD50s = 0.52 and 0.996 mg/kg in female and male rats, respectively).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lin, L., Cordell, G.A., Ni, C., et al. Gelsamydine, an indole alkaloid from Gelsemium elegans with two monoterpene units. The Journal of Organic Chemistry 54(13), 3199-3202 (1989).

    2. Liu, M., Shen, J., Liu, H., et al. Gelsenicine from Gelsemium elegans attenuates neuropathic and inflammatory pain in mice. Biol. Pharm. Bull. 34(12), 1877-1880 (2011).

    3. Li, Y.J., Yang, K., Long, X.M., et al. Toxicity assessment of gelsenicine and the search for effective antidotes. Hum. Exp. Toxicol. 41, 1-13 (2022).