MedKoo Cat#: 563751 | Name: Integerrimine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Integerrimine is a natural pyrrolizidine alkaloid, possessing significant hepatotoxicity to humans and animals after metabolic activation by liver P450 enzymes.

Chemical Structure

Integerrimine
Integerrimine
CAS#480-79-5

Theoretical Analysis

MedKoo Cat#: 563751

Name: Integerrimine

CAS#: 480-79-5

Chemical Formula: C18H25NO5

Exact Mass: 335.1733

Molecular Weight: 335.40

Elemental Analysis: C, 64.46; H, 7.51; N, 4.18; O, 23.85

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Integerrimine; Senecionine; Squalidin; Squalidine;
IUPAC/Chemical Name
(15Z)-12-hydroxysenecionan-11,16-dione
InChi Key
HKODIGSRFALUTA-JTLQZVBZSA-N
InChi Code
InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1
SMILES Code
[H][C@@]12[C@]([H])(OC(/C(C[C@H]([C@]3(O)C)C)=C\C)=O)CCN1CC=C2COC3=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 335.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Influence of grass pellet production on pyrrolizidine alkaloids occurring in Senecio aquaticus-infested grassland. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2018 Apr;35(4):750-759. doi: 10.1080/19440049.2018.1430901. Epub 2018 Feb 23. PubMed PMID: 29377789. 5: Cheng D, Nguyen VT, Ndihokubwayo N, Ge J, Mulder PPJ. Pyrrolizidine alkaloid variation in Senecio vulgaris populations from native and invasive ranges. PeerJ. 2017 Aug 14;5:e3686. doi: 10.7717/peerj.3686. eCollection 2017. PubMed PMID: 28828276; PubMed Central PMCID: PMC5560238. 6: Cheng X, Liao M, Diao X, Sun Y, Zhang L. Screening and identification of metabolites of two kinds of main active ingredients and hepatotoxic pyrrolizidine alkaloids in rat after lavage Farfarae Flos extract by UHPLC-Q-TOF-MS mass spectrometry. Biomed Chromatogr. 2018 Feb;32(2). doi: 10.1002/bmc.4047. Epub 2017 Aug 18. PubMed PMID: 28702943. 7: Liu W, Li X, Zhou B, Fang S, Ho W, Chen H, Liang H, Ye L, Tang J. Differential induction of apoptosis and autophagy by pyrrolizidine alkaloid clivorine in human hepatoma Huh-7.5 cells and its toxic implication. PLoS One. 2017 Jun 26;12(6):e0179379. doi: 10.1371/journal.pone.0179379. eCollection 2017. PubMed PMID: 28650983; PubMed Central PMCID: PMC5484491. 8: Yang M, Ruan J, Gao H, Li N, Ma J, Xue J, Ye Y, Fu PP, Wang J, Lin G. First evidence of pyrrolizidine alkaloid N-oxide-induced hepatic sinusoidal obstruction syndrome in humans. Arch Toxicol. 2017 Dec;91(12):3913-3925. doi: 10.1007/s00204-017-2013-y. Epub 2017 Jun 15. PubMed PMID: 28620673. 9: Martinello M, Borin A, Stella R, Bovo D, Biancotto G, Gallina A, Mutinelli F. Development and validation of a QuEChERS method coupled to liquid chromatography and high resolution mass spectrometry to determine pyrrolizidine and tropane alkaloids in honey. Food Chem. 2017 Nov 1;234:295-302. doi: 10.1016/j.foodchem.2017.04.186. Epub 2017 May 2. PubMed PMID: 28551239. 10: Preliasco M, Gardner D, Moraes J, González AC, Uriarte G, Rivero R. Senecio grisebachii Baker: Pyrrolizidine alkaloids and experimental poisoning in calves. Toxicon. 2017 Jul;133:68-73. doi: 10.1016/j.toxicon.2017.05.004. Epub 2017 May 3. PubMed PMID: 28478055. 11: Zhang W, Huai W, Zhang Y, Shen J, Tang X, Xie X, Wang K, Fan H. Ultra-Performance Liquid Chromatography Hyphenated with Quadrupole-Orbitrap Mass Spectrometry for Simultaneous Determination of Necine-Core-Structure Pyrrolizidine Alkaloids in Crotalaria sessiliflora L. without all Corresponding Standards. Phytochem Anal. 2017 Sep;28(5):365-373. doi: 10.1002/pca.2683. Epub 2017 Mar 23. PubMed PMID: 28332747. 12: Yang X, Wang H, Ni HM, Xiong A, Wang Z, Sesaki H, Ding WX, Yang L. Inhibition of Drp1 protects against senecionine-induced mitochondria-mediated apoptosis in primary hepatocytes and in mice. Redox Biol. 2017 Aug;12:264-273. doi: 10.1016/j.redox.2017.02.020. Epub 2017 Mar 2. PubMed PMID: 28282614; PubMed Central PMCID: PMC5344326. 13: Liu X, Klinkhamer PGL, Vrieling K. The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips. Phytochemistry. 2017 Jun;138:93-103. doi: 10.1016/j.phytochem.2017.02.027. Epub 2017 Mar 6. PubMed PMID: 28267991. 14: Cao K, Xu Y, Mu X, Zhang Q, Wang R, Lv J. Sensitive determination of pyrrolizidine alkaloids in Tussilago farfara L. by field-amplified, sample-stacking, sweeping micellar electrokinetic chromatography. J Sep Sci. 2016 Nov;39(21):4243-4250. doi: 10.1002/jssc.201600762. PubMed PMID: 27673325. 15: Mollinedo P, Vila JL, Arando H, Sauvain M, Deharo E, Bravo JA. Anti-infective assessment of Senecio smithioides (Asteraceae) and isolation of 9-oxoeuryopsin, a furanoeremophilane-type sesquiterpene with antiplasmodial activity. Nat Prod Res. 2015 Nov 25:1-4. [Epub ahead of print] PubMed PMID: 26606687. 16: Martins CH, Cunha BP, Solferini VN, Trigo JR. Feeding on Host Plants with Different Concentrations and Structures of Pyrrolizidine Alkaloids Impacts the Chemical-Defense Effectiveness of a Specialist Herbivore. PLoS One. 2015 Oct 30;10(10):e0141480. doi: 10.1371/journal.pone.0141480. eCollection 2015. PubMed PMID: 26517873; PubMed Central PMCID: PMC4627748. 17: Mudge EM, Jones AM, Brown PN. Quantification of pyrrolizidine alkaloids in North American plants and honey by LC-MS: single laboratory validation. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(12):2068-74. doi: 10.1080/19440049.2015.1099743. Epub 2015 Oct 20. PubMed PMID: 26482059. 18: Sandini TM, Udo MS, Reis-Silva TM, Sanches D, Bernardi MM, Flório JC, Spinosa Hde S. Prenatal exposure to integerrimine N-oxide enriched butanolic residue from Senecio brasiliensis affects behavior and striatal neurotransmitter levels of rats in adulthood. Int J Dev Neurosci. 2015 Dec;47(Pt B):157-64. doi: 10.1016/j.ijdevneu.2015.09.003. Epub 2015 Sep 28. PubMed PMID: 26416213. 19: Chizzola R. Pyrrolizidine Alkaloids in Adenostyles alliariae and A. glabra from the Austrian Alps. Nat Prod Commun. 2015 Jul;10(7):1179-80. PubMed PMID: 26411004. 20: Chen P, Wang Y, Chen L, Jiang W, Niu Y, Shao Q, Gao L, Zhao Q, Yan L, Wang S. Comparison of the anti-inflammatory active constituents and hepatotoxic pyrrolizidine alkaloids in two Senecio plants and their preparations by LC-UV and LC-MS. J Pharm Biomed Anal. 2015 Nov 10;115:260-71. doi: 10.1016/j.jpba.2015.07.014. Epub 2015 Jul 26. PubMed PMID: 26257293.