An alkaloid with diverse biological activities
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Brucine

Item No. 27221

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3-dimethoxy-strychnidin-10-one
CAS Number
357-57-3
Synonyms
  • 2,3-Dimethoxystrychnine
Molecular Formula
C23H26N2O4
Formula Weight
394.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: 10 mg/mlChloroform: 30 mg/ml
λmax
210, 264, 304 nm
SMILES
COC(C(OC)=C1)=CC2=C1N3C(C[C@@]4([H])[C@@]5([H])[C@@]3([H])[C@@]26[C@](N7CC6)([H])C[C@@]5([H])C(C7)=CCO4)=O
InChi Code
InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1
InChi Key
RRKTZKIUPZVBMF-IBTVXLQLSA-N
Origin
Plant/Strychnos nux-vomica seeds
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 g

    $41

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    25 g

    $74

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    50 g

    $140

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    100 g

    $255

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    Cayman Chemical
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    Product Description

    Brucine is an alkaloid that has been found in the seeds of the S. nux-vomica tree and has diverse biological activities, including anti-inflammatory, anticancer, and antioxidant properties.1 It inhibits prostaglandin E2 (PGE2; Item No. 14010) production induced by LPS in vitro.2 Topical administration of brucine decreases synoviocyte proliferation and reduces paw and joint swelling in a rat model of adjuvant-induced arthritis and decreases swelling in a mouse model of xylene-induced ear edema. Brucine (4 and 8 mg/kg per day) reduces tumor incidence, number, and volume in a rat model of mammary gland tumorigenesis induced by 7,12-dimethylbenz(a)anthracene (DMBA).1 It prevents decreases in superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPX) activity and increases the level of glutathione (GSH) in mammary tissues, as well as reduces markers of lipid peroxidation in plasma and mammary tissue. Brucine also allosterically enhances the effect of low, but not high, concentrations of acetylcholine at M1 muscarinic acetylcholine receptors.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Saminathan, U., Pugalendhi, P., Subramaniyan, S., et al. Biochemical studies evaluating the chemopreventive potential of brucine in chemically induced mammary carcinogenesis of rats. Toxicol. Mech. Methods 29(1), 8-17 (2019).

    2. Wu, P., Liang, Q., Feng, P., et al. A novel brucine gel transdermal delivery system designed for anti-inflammatory and analgesic activities. Int. J. Mol. Sci. 18(4), e757 (2017).

    3. Birdsall, N.J., Farries, T., Gharagozloo, P., et al. Selective allosteric enhancement of the binding and actions of acetylcholine at muscarinic receptor subtypes. Life Sci. 60(13-14), 1047-1052 (1997).