A neurotoxic pyridoxine antimetabolite
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Ginkgotoxin

Item No. 33460

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-hydroxy-4-(methoxymethyl)-6-methyl-3-pyridinemethanol
CAS Number
1464-33-1
Synonyms
  • MPN
  • 4'-O-Methylpyridoxine
  • 4’-Methoxypyridoxine
Molecular Formula
C9H13NO3
Formula Weight
183.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 5 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
OC1=C(COC)C(CO)=CN=C1C
InChi Code
InChI=1S/C9H13NO3/c1-6-9(12)8(5-13-2)7(4-11)3-10-6/h3,11-12H,4-5H2,1-2H3
InChi Key
SVINQHQHARVZFF-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $54

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    10 mg

    $102

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    25 mg

    $238

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    50 mg

    $444

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    Product Description

    Ginkgotoxin is a pyridoxine antimetabolite that has been found in G. biloba.1,2 It inhibits pyridoxal kinase (Ki = 3 µM), the enzyme that converts pyridoxine into its active form, pyridoxal 5’-phosphate (PLP; Item No. 20352).3 Ginkgotoxin (200-1,000 µM) induces seizure-like behavior in zebrafish larvae, an effect that can be reversed by PLP or GABA.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wada, K., Ishigaki, S., Ueda, K., et al. An antivitamin B6, 4'-methoxypyridoxine, from the seed of Ginkgo biloba L. Chem. Pharm. Bull. 33(8), 3555-3557 (1985).

    2. Arenz, A., Klein, M.K., Fiehe, K., et al. Occurrence of neurotoxic 4'-O-methylpyridoxine in Ginkgo biloba leaves, Ginkgo medications and Japanese Ginkgo food. Planta Med. 62(6), 548-551 (1996).

    3. Gandhi, A.K., Desai, J.V., Ghatge, M.S., et al. Crystal structures of human pyridoxal kinase in complex with the neurotoxins, ginkgotoxin and theophylline: Insights into pyridoxal kinase inhibition. PLoS One 7(7), e40954 (2012).

    4. Lee, G.-H., Sung, S.-Y., Chang, W.-N., et al. Zebrafish larvae exposed to ginkgotoxin exhibit seizure-like behavior that is relieved by pyridoxal-5'-phosphate, GABA and anti-epileptic drugs. Dis. Model. Mech. 5(6), 785-795 (2012).