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MedKoo Cat#: 461247 | Name: Retrorsine
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Description:

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

Retrorsine is a hepatotoxic pyrrolizidine alkaloid present in plants of the Senecio genus.

Chemical Structure

Retrorsine
Retrorsine
CAS#480-54-6

Theoretical Analysis

MedKoo Cat#: 461247

Name: Retrorsine

CAS#: 480-54-6

Chemical Formula: C18H25NO6

Exact Mass: 351.1682

Molecular Weight: 351.39

Elemental Analysis: C, 61.52; H, 7.17; N, 3.99; O, 27.32

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Retrorsine; -Longilobine; NSC 107659; NSC-107659; NSC107659; Retrorsin;
IUPAC/Chemical Name
(5R,6S,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
InChi Key
BCJMNZRQJAVDLD-CQRYIUNCSA-N
InChi Code
InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-/m1/s1
SMILES Code
O=C(O[C@]1([H])CCN2[C@]1([H])C(COC([C@](CO)(O)[C@H](C)C/3)=O)=CC2)C3=C/C
Appearance
Solid powder
Purity
>95% (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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 351.39 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
1: Jahouh F, Marongiu F, Serra MP, Laconi E, Banoub J. Gas-phase fragmentation of the N-oxide and N-hydroxylated derivatives of retrorsine using liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Rapid Commun Mass Spectrom. 2015 Oct 15;29(19):1733-48. doi: 10.1002/rcm.7276. PubMed PMID: 26331923. 2: Fashe MM, Juvonen RO, Petsalo A, Rahnasto-Rilla M, Auriola S, Soininen P, Vepsäläinen J, Pasanen M. Identification of a new reactive metabolite of pyrrolizidine alkaloid retrorsine: (3H-pyrrolizin-7-yl)methanol. Chem Res Toxicol. 2014 Nov 17;27(11):1950-7. doi: 10.1021/tx5002964. Epub 2014 Oct 21. PubMed PMID: 25295702. 3: Tu M, Li L, Lei H, Ma Z, Chen Z, Sun S, Xu S, Zhou H, Zeng S, Jiang H. Involvement of organic cation transporter 1 and CYP3A4 in retrorsine-induced toxicity. Toxicology. 2014 Aug 1;322:34-42. doi: 10.1016/j.tox.2014.04.007. Epub 2014 May 4. PubMed PMID: 24799337. 4: Chen YH, Chang MH, Chien CS, Wu SH, Yu CH, Chen HL. Contribution of mature hepatocytes to small hepatocyte-like progenitor cells in retrorsine-exposed rats with chimeric livers. Hepatology. 2013 Mar;57(3):1215-24. doi: 10.1002/hep.26104. Epub 2013 Feb 15. PubMed PMID: 23080021. 5: Maeda H, Ota Y, Wang Y, Ramachandran K, Montgomery RA, Williams GM, Sun Z. Contribution of extrahepatic small cells resembling small hepatocyte-like progenitor cells to liver mass maintenance in transplantation model of retrorsine-pretreated liver. Springerplus. 2013 Sep 8;2:446. doi: 10.1186/2193-1801-2-446. eCollection 2013. PubMed PMID: 24083100; PubMed Central PMCID: PMC3786066. 6: Janeš D, Kreft S. TLC densitometric method for screening of lycopsamine in comfrey root (Symphytum officinale L.) extracts using retrorsine as a reference compound. Acta Pharm. 2014 Dec;64(4):503-8. doi: 10.2478/acph-2014-0031. PubMed PMID: 25531790. 7: Tachibana A, Tateno C, Yoshizato K. Repopulation of the immunosuppressed retrorsine-treated infant rat liver with human hepatocytes. Xenotransplantation. 2013 Jul-Aug;20(4):227-38. doi: 10.1111/xen.12037. Epub 2013 May 20. PubMed PMID: 23683097. 8: Han J, Liang A, Yi Y. [Developmental toxicity of retrorsine on mouse embryos in vitro]. Zhongguo Zhong Yao Za Zhi. 2011 Jul;36(14):1901-4. Chinese. PubMed PMID: 22016956. 9: Maeda H, Shigoka M, Wang Y, Fu Y, Wesson RN, Lin Q, Montgomery RA, Enzan H, Sun Z. Disappearance of GFP-positive hepatocytes transplanted into the liver of syngeneic wild-type rats pretreated with retrorsine. PLoS One. 2014 May 5;9(5):e95880. doi: 10.1371/journal.pone.0095880. eCollection 2014. PubMed PMID: 24796859; PubMed Central PMCID: PMC4010421. 10: Best DH, Butz GM, Coleman WB. Cytokine-dependent activation of small hepatocyte-like progenitor cells in retrorsine-induced rat liver injury. Exp Mol Pathol. 2010 Feb;88(1):7-14. doi: 10.1016/j.yexmp.2009.10.009. Epub 2009 Oct 27. PubMed PMID: 19874816. 11: Best DH, Coleman WB. Liver regeneration by small hepatocyte-like progenitor cells after necrotic injury by carbon tetrachloride in retrorsine-exposed rats. Exp Mol Pathol. 2010 Oct;89(2):92-8. doi: 10.1016/j.yexmp.2010.06.007. Epub 2010 Jul 1. PubMed PMID: 20599936. 12: Zhou XF, Wang Q, Chu JX, Liu AL. Effects of retrorsine on mouse hepatocyte proliferation after liver injury. World J Gastroenterol. 2006 Mar 7;12(9):1439-42. PubMed PMID: 16552817; PubMed Central PMCID: PMC4124326. 13: Gordon GJ, Coleman WB, Grisham JW. Bax-mediated apoptosis in the livers of rats after partial hepatectomy in the retrorsine model of hepatocellular injury. Hepatology. 2000 Aug;32(2):312-20. PubMed PMID: 10915738. 14: Chu PS, Lamé MW, Segall HJ. In vivo metabolism of retrorsine and retrorsine-N-oxide. Arch Toxicol. 1993;67(1):39-43. PubMed PMID: 8452478. 15: Picard C, Lambotte L, Starkel P, Sempoux C, Saliez A, Van Den Berge V, de Saeger C, Horsmans Y. Retrorsine: a kinetic study of its influence on rat liver regeneration in the portal branch ligation model. J Hepatol. 2003 Jul;39(1):99-105. PubMed PMID: 12821050. 16: Aston N, Morris P, Tanner S. Retrorsine in breast milk influences copper handling in suckling rat pups. J Hepatol. 1996 Nov;25(5):748-55. PubMed PMID: 8938555. 17: Wang YP, Fu PP, Chou MW. Metabolic activation of the tumorigenic pyrrolizidine alkaloid, retrorsine, leading to DNA adduct formation in vivo. Int J Environ Res Public Health. 2005 Apr;2(1):74-9. PubMed PMID: 16705803; PubMed Central PMCID: PMC3814699. 18: Gordon GJ, Coleman WB, Grisham JW. Induction of cytochrome P450 enzymes in the livers of rats treated with the pyrrolizidine alkaloid retrorsine. Exp Mol Pathol. 2000 Aug;69(1):17-26. PubMed PMID: 10891289. 19: Laconi S, Curreli F, Diana S, Pasciu D, De Filippo G, Sarma DS, Pani P, Laconi E. Liver regeneration in response to partial hepatectomy in rats treated with retrorsine: a kinetic study. J Hepatol. 1999 Dec;31(6):1069-74. PubMed PMID: 10604581. 20: Lin G, Nnane IP, Cheng TY. The effects of pretreatment with glycyrrhizin and glycyrrhetinic acid on the retrorsine-induced hepatotoxicity in rats. Toxicon. 1999 Sep;37(9):1259-70. PubMed PMID: 10400287.