A metabolite of monocrotaline
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Parent Compound(s)
16666Monocrotaline
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Monocrotaline N-oxide

Item No. 45707

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,5,8,10,12,13,13aR,13bR-octahydro-4,5-dihydroxy-3R,4S,5S-trimethyl-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 11-oxide
CAS Number
35337-98-5
Molecular Formula
C16H23NO7
Formula Weight
341.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly Soluble: 1-10 mg/mlWater: Slightly soluble: 0.1-1 mg/ml
SMILES
O=C(O[C@@]1([H])[C@@]2([H])C(CO3)=CC[N+]2([O-])CC1)[C@H](C)[C@@](C)(O)[C@@](C)(O)C3=O
InChi Code
InChI=1S/C16H23NO7/c1-9-13(18)24-11-5-7-17(22)6-4-10(12(11)17)8-23-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-,17?/m0/s1
InChi Key
LHVAZUAALQTANZ-ANYXPJNNSA-N
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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    1 mg

    $65

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    5 mg

    $211

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    10 mg

    $325

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    Product Description

    Monocrotaline N-oxide is a metabolite of monocrotaline (Item No. 16666).1 It is formed from monocrotaline by the cytochrome P450 (CYP) isoform CYP3A. However, monocrotaline N-oxide can be converted back to monocrotaline by human liver microsomes and intestinal bacteria.2,3 Unlike the toxic monocrotaline metabolite monocrotaline pyrrole, monocrotaline N-oxide is not toxic to rats.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, Y.P., Yan, J., Beger, R.D., et al. Metabolic activation of the tumorigenic pyrrolizidine alkaloid, monocrotaline, leading to DNA adduct formation in vivo. Cancer Lett. 226(1), 27-35 (2005).

    2. Wang, Y.P., Yan, J., Fu, P.P., et al. Human liver microsomal reduction of pyrrolizidine alkaloid N-oxides to form the corresponding carcinogenic parent alkaloid. Toxicol. Lett. 155(3), 411-420 (2005).

    3. Tang, J., Wang, Z., Akao, T., et al. Human intestinal bacteria mediate reduction of the n-oxides of isoline and monocrotaline to the corresponding parent alkaloids. Asian J. Chem. 25(4), 2027-2030 (2013).

    4. Bruner, L.H., Carpenter, L.J., Hamlow, P., et al. Effect of a mixed function oxidase inducer and inhibitor on monocrotaline pyrrole pneumotoxicity. Toxicol. Appl. Pharmacol. 85(3), 416-427 (1986).