MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 330129 | Name: Norbormide

Description:

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

Norbormide, also known as Raticate, Shoxin, is a toxic compound used as a rodenticide. It has several mechanisms of action, acting as a vasoconstrictor and calcium channel blocker, but is selectively toxic to rats and has relatively low toxicity to other species, due to a species specific action of opening the permeability transition pores in rat mitochondria.

Chemical Structure

Norbormide
Norbormide
CAS#991-42-4

Theoretical Analysis

MedKoo Cat#: 330129

Name: Norbormide

CAS#: 991-42-4

Chemical Formula: C33H25N3O3

Exact Mass: 511.1896

Molecular Weight: 511.58

Elemental Analysis: C, 77.48; H, 4.93; N, 8.21; O, 9.38

Price and Availability

Size Price Availability Quantity
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Norbormide; Raticate; Shoxin; MCN 1025; Mcneil 1025; S 6999; S-6,999;
IUPAC/Chemical Name
(10E)-8-[hydroxy(phenyl)pyridin-2-ylmethyl]-10-[phenyl(pyridin-2-yl)methylidene]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
InChi Key
DNTHHIVFNQZZRD-CYYJNZCTSA-N
InChi Code
InChI=1S/C33H25N3O3/c37-31-28-22-19-23(33(39,21-13-5-2-6-14-21)25-16-8-10-18-35-25)29(30(28)32(38)36-31)27(22)26(20-11-3-1-4-12-20)24-15-7-9-17-34-24/h1-19,22,28-30,39H,(H,36,37,38)/b27-26+
SMILES Code
O=C(N1)C2C(/C3=C(C4=CC=CC=C4)\C5=NC=CC=C5)C=C(C(C6=CC=CC=C6)(O)C7=NC=CC=C7)C3C2C1=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
>2 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Norbormide, also known as Raticate, Shoxin, is a toxic compound used as a rodenticide.
In vitro activity:
Both norbormide (a racemic mixture of endo and exo isomers) and glibenclamide inhibited KATP currents in rat and mouse caudal artery myocytes, as well as in gastric fundus smooth muscle cells. In rat caudal artery rings, norbormide-induced contraction was partially reverted by the KATP channel opener pinacidil. Reference: Front Pharmacol. 2019 May 23;10:598. https://pubmed.ncbi.nlm.nih.gov/31191321/
In vivo activity:
In urinary bladder and tracheal rings, norbormide inhibited contractile responses to carbachol only at the higher concentration (50 microM). In single gastric fundus myocytes, 50 microM norbormide inhibited L-type Ca(2+) current (I(Ca(L))) by about 60%, neither affecting both activation and inactivation rates of the current nor the current-voltage curve along the voltage axis. Reference: Eur J Pharmacol. 2003 Jun 6;470(3):185-91. https://pubmed.ncbi.nlm.nih.gov/12798957/

Preparing Stock Solutions

The following data is based on the product molecular weight 511.58 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
Formulation protocol:
1. Saponara S, Fusi F, Spiga O, Trezza A, Hopkins B, Brimble MA, Rennison D, Bova S. The Selective Rat Toxicant Norbormide Blocks KATP Channels in Smooth Muscle Cells But Not in Insulin-Secreting Cells. Front Pharmacol. 2019 May 23;10:598. doi: 10.3389/fphar.2019.00598. PMID: 31191321; PMCID: PMC6540933. 2. Fusi F, Saponara S, Sgaragli G, Cargnelli G, Bova S. Ca(2+) entry blocking and contractility promoting actions of norbormide in single rat caudal artery myocytes. Br J Pharmacol. 2002 Oct;137(3):323-8. doi: 10.1038/sj.bjp.0704877. PMID: 12237251; PMCID: PMC1573499. 3. Bova S, Cavalli M, Cima L, Luciani S, Saponara S, Sgaragli G, Cargnelli G, Fusi F. Relaxant and Ca2+ channel blocking properties of norbormide on rat non-vascular smooth muscles. Eur J Pharmacol. 2003 Jun 6;470(3):185-91. doi: 10.1016/s0014-2999(03)01797-7. PMID: 12798957.
In vitro protocol:
1. Saponara S, Fusi F, Spiga O, Trezza A, Hopkins B, Brimble MA, Rennison D, Bova S. The Selective Rat Toxicant Norbormide Blocks KATP Channels in Smooth Muscle Cells But Not in Insulin-Secreting Cells. Front Pharmacol. 2019 May 23;10:598. doi: 10.3389/fphar.2019.00598. PMID: 31191321; PMCID: PMC6540933. 2. Fusi F, Saponara S, Sgaragli G, Cargnelli G, Bova S. Ca(2+) entry blocking and contractility promoting actions of norbormide in single rat caudal artery myocytes. Br J Pharmacol. 2002 Oct;137(3):323-8. doi: 10.1038/sj.bjp.0704877. PMID: 12237251; PMCID: PMC1573499.
In vivo protocol:
1. Bova S, Cavalli M, Cima L, Luciani S, Saponara S, Sgaragli G, Cargnelli G, Fusi F. Relaxant and Ca2+ channel blocking properties of norbormide on rat non-vascular smooth muscles. Eur J Pharmacol. 2003 Jun 6;470(3):185-91. doi: 10.1016/s0014-2999(03)01797-7. PMID: 12798957.
1: D'Amore C, Orso G, Fusi F, Pagano MA, Miotto G, Forgiarini A, De Martin S, Castellani G, Ribaudo G, Rennison D, Brimble MA, Hopkins B, Ferrarese A, Bova S. An NBD Derivative of the Selective Rat Toxicant Norbormide as a New Probe for Living Cell Imaging. Front Pharmacol. 2016 Sep 23;7:315. eCollection 2016. PubMed PMID: 27721792; PubMed Central PMCID: PMC5034647. 2: Choi H, Conole D, Atkinson DJ, Laita O, Jay-Smith M, Pagano MA, Ribaudo G, Cavalli M, Bova S, Hopkins B, Brimble MA, Rennison D. Fatty Acid-Derived Pro-Toxicants of the Rat Selective Toxicant Norbormide. Chem Biodivers. 2016 Jun;13(6):762-75. doi: 10.1002/cbdv.201500241. Epub 2016 Jun 2. PubMed PMID: 27144301. 3: Rennison D, Laita O, Conole D, Jay-Smith M, Knauf J, Bova S, Cavalli M, Hopkins B, Linthicum DS, Brimble MA. Prodrugs of N-dicarboximide derivatives of the rat selective toxicant norbormide. Bioorg Med Chem. 2013 Sep 15;21(18):5886-99. doi: 10.1016/j.bmc.2013.06.071. Epub 2013 Jul 10. PubMed PMID: 23920483. 4: Rennison D, Laita O, Bova S, Cavalli M, Hopkins B, Linthicum DS, Brimble MA. Design and synthesis of prodrugs of the rat selective toxicant norbormide. Bioorg Med Chem. 2012 Jul 1;20(13):3997-4011. doi: 10.1016/j.bmc.2012.05.014. Epub 2012 May 15. PubMed PMID: 22658693. 5: Zulian A, Sileikytė J, Petronilli V, Bova S, Dabbeni-Sala F, Cargnelli G, Rennison D, Brimble MA, Hopkins B, Bernardi P, Ricchelli F. The translocator protein (peripheral benzodiazepine receptor) mediates rat-selective activation of the mitochondrial permeability transition by norbormide. Biochim Biophys Acta. 2011 Dec;1807(12):1600-5. doi: 10.1016/j.bbabio.2011.08.007. Epub 2011 Aug 26. PubMed PMID: 21889488. 6: Ravindran S, Hopkins B, Bova S, Tingle M. In vivo metabolism of norbormide in rats and mice. Environ Toxicol Pharmacol. 2009 Jul;28(1):147-51. doi: 10.1016/j.etap.2009.03.013. Epub 2009 Apr 8. PubMed PMID: 21783995. 7: Ravindran S, Hopkins B, Bova S, Rennison D, Brimble M, Tingle M. In vitro metabolism of norbormide in rat, mouse and guinea pig liver preparations. Environ Toxicol Pharmacol. 2009 Jan;27(1):144-8. doi: 10.1016/j.etap.2008.09.007. Epub 2008 Oct 19. PubMed PMID: 21783932. 8: Zulian A, Petronilli V, Bova S, Dabbeni-Sala F, Cargnelli G, Cavalli M, Rennison D, Stäb J, Laita O, Lee DJ, Brimble MA, Hopkins B, Bernardi P, Ricchelli F. Assessing the molecular basis for rat-selective induction of the mitochondrial permeability transition by norbormide. Biochim Biophys Acta. 2007 Jul;1767(7):980-8. Epub 2007 Apr 14. PubMed PMID: 17509521. 9: Rennison D, Bova S, Cavalli M, Ricchelli F, Zulian A, Hopkins B, Brimble MA. Synthesis and activity studies of analogues of the rat selective toxicant norbormide. Bioorg Med Chem. 2007 Apr 15;15(8):2963-74. Epub 2007 Feb 11. PubMed PMID: 17321141. 10: Ricchelli F, Dabbeni-Sala F, Petronilli V, Bernardi P, Hopkins B, Bova S. Species-specific modulation of the mitochondrial permeability transition by norbormide. Biochim Biophys Acta. 2005 Jun 30;1708(2):178-86. Epub 2005 Mar 19. PubMed PMID: 15953474. 11: Mahteme H, Sundin A, Larsson B, Khamis H, Arow K, Graf W. 5-FU uptake in peritoneal metastases after pretreatment with radioimmunotherapy or vasoconstriction: an autoradiographic study in the rat. Anticancer Res. 2005 Mar-Apr;25(2A):917-22. PubMed PMID: 15868928. 12: Cavalli M, Omiciuolo L, Cargnelli G, Cima L, Hopkins B, Bova S. Distribution of the vasoconstrictor and vasorelaxant effects of norbormide along the vascular tree of the rat. Life Sci. 2004 Sep 17;75(18):2157-65. PubMed PMID: 15325842. 13: Steel PJ, Brimble MA, Hopkins B, Rennison D. Two stereoisomers of the rat toxicant norbormide. Acta Crystallogr C. 2004 May;60(Pt 5):o374-6. Epub 2004 Apr 30. PubMed PMID: 15131397. 14: Bova S, Cavalli M, Cima L, Luciani S, Saponara S, Sgaragli G, Cargnelli G, Fusi F. Relaxant and Ca2+ channel blocking properties of norbormide on rat non-vascular smooth muscles. Eur J Pharmacol. 2003 Jun 6;470(3):185-91. PubMed PMID: 12798957. 15: Neri G, Tortorella C, Andreis PG, Bova S, Malendowicz LK, Ziolkowska A, Nussdorfer GG. Norbormide enhances late steps of steroid-hormone synthesis in rat and mouse adrenal cortex. J Steroid Biochem Mol Biol. 2003 Mar;84(4):479-83. PubMed PMID: 12732293. 16: Fusi F, Saponara S, Sgaragli G, Cargnelli G, Bova S. Ca(2+) entry blocking and contractility promoting actions of norbormide in single rat caudal artery myocytes. Br J Pharmacol. 2002 Oct;137(3):323-8. PubMed PMID: 12237251; PubMed Central PMCID: PMC1573499. 17: Nadian A, Lindblom L. Studies on the development of a microencapsulated delivery system for norbormide, a species-specific acute rodenticide. Int J Pharm. 2002 Aug 21;242(1-2):63-8. PubMed PMID: 12176226. 18: Bova S, Cima L, Golovina V, Luciani S, Cargnelli G. Norbormide: a calcium entry blocker with selective vasoconstrictor activity in rat peripheral arteries. Cardiovasc Drug Rev. 2001 Fall;19(3):226-33. Review. PubMed PMID: 11607040. 19: Bova S, Trevisi L, Cima L, Luciani S, Golovina V, Cargnelli G. Signaling mechanisms for the selective vasoconstrictor effect of norbormide on the rat small arteries. J Pharmacol Exp Ther. 2001 Feb;296(2):458-63. PubMed PMID: 11160631. 20: Bova S, Cargnelli G, D'Amato E, Forti S, Yang Q, Trevisi L, Debetto P, Cima L, Luciani S, Padrini R. Calcium-antagonist effects of norbormide on isolated perfused heart and cardiac myocytes of guinea-pig: a comparison with verapamil. Br J Pharmacol. 1997 Jan;120(1):19-24. PubMed PMID: 9117093; PubMed Central PMCID: PMC1564351.