Date published: 2025-11-20

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Monocrotaline N-Oxide (CAS 35337-98-5)

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Alternate Names:
(3R,4S,5S,13aR,13bR)-4,5,8,10,12,13,13a,13b-Octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione 11-Oxide; (13α,14α)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione 4-Oxide
CAS Number:
35337-98-5
Molecular Weight:
341.36
Molecular Formula:
C16H23NO7
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Monocrotaline N-Oxide is a compound of interest in the field of toxicology and environmental research. It is closely related to monocrotaline, a pyrrolizidine alkaloid, and is used to study the metabolic activation and detoxification pathways of these types of alkaloids. Researchers employ Monocrotaline N-Oxide to understand the enzymatic processes involved in the oxidation of pyrrolizidine alkaloids, which can lead to the formation of reactive metabolites with potential toxicity. Additionally, it serves as an analytical standard in the detection and quantification of pyrrolizidine alkaloid contamination in foodstuffs and herbal products. In ecological studies, Monocrotaline N-Oxide is utilized to examine the impact of pyrrolizidine alkaloids on wildlife and livestock that may ingest plants containing these compounds. Furthermore, it helps in the investigation of the chemical stability of pyrrolizidine alkaloids under various environmental conditions, contributing to risk assessment and management strategies.


Monocrotaline N-Oxide (CAS 35337-98-5) References

  1. Development of enzyme-linked immunosorbent assays for the hepatotoxic alkaloids riddelliine and riddelliine N-oxide.  |  Lee, ST., et al. 2001. J Agric Food Chem. 49: 4144-51. PMID: 11513723
  2. Human liver microsomal reduction of pyrrolizidine alkaloid N-oxides to form the corresponding carcinogenic parent alkaloid.  |  Wang, YP., et al. 2005. Toxicol Lett. 155: 411-20. PMID: 15649625
  3. Metabolic activation of the tumorigenic pyrrolizidine alkaloid, monocrotaline, leading to DNA adduct formation in vivo.  |  Wang, YP., et al. 2005. Cancer Lett. 226: 27-35. PMID: 16004930
  4. If you've got it, flaunt it: ingested alkaloids affect corematal display behavior in the salt marsh moth, Estigmene acrea.  |  Jordan, AT., et al. 2005. J Insect Sci. 5: 1. PMID: 16299591
  5. Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine.  |  Xia, Q., et al. 2008. Toxicol Lett. 178: 77-82. PMID: 18395999
  6. Metabolic activation of retronecine and retronecine N-oxide - formation of DHP-derived DNA adducts.  |  Yan, J., et al. 2008. Toxicol Ind Health. 24: 181-8. PMID: 18842697
  7. Hepatic cytochrome P450s play a major role in monocrotaline-induced renal toxicity in mice.  |  Yao, J., et al. 2014. Acta Pharmacol Sin. 35: 292-300. PMID: 24362331
  8. Paternal allocation of sequestered plant pyrrolizidine alkaloid to eggs in the danaine butterfly, Danaus gilippus.  |  Dussourd, DE., et al. 1989. Experientia. 45: 896-8. PMID: 2776861
  9. Pyrrolizidine alkaloid-derived DNA adducts are common toxicological biomarkers of pyrrolizidine alkaloid N-oxides.  |  He, X., et al. 2017. J Food Drug Anal. 25: 984-991. PMID: 28987376
  10. Microbiota-Derived Metabolite Trimethylamine N-Oxide Protects Mitochondrial Energy Metabolism and Cardiac Functionality in a Rat Model of Right Ventricle Heart Failure.  |  Videja, M., et al. 2020. Front Cell Dev Biol. 8: 622741. PMID: 33520996
  11. Simultaneous determination of monocrotaline and its N-oxide metabolite in rat plasma using LC-MS/MS: Application to a pharmacokinetic study.  |  Lin, F., et al. 2021. Biomed Chromatogr. 35: e5207. PMID: 34184288
  12. Activation of monocrotaline, fulvine and their derivatives to toxic pyrroles by some thiols.  |  Juneja, TR., et al. 1984. Toxicol Lett. 21: 185-9. PMID: 6426098
  13. Metabolic activation of pyrrolizidine alkaloids by human, rat and avocado microsomes.  |  Couet, CE., et al. 1996. Toxicon. 34: 1058-61. PMID: 8896199

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Monocrotaline N-Oxide, 5 mg

sc-484410
5 mg
$311.00