Gallopamil, (-)- | CAS#36622-40-9 | calcium channel blocker

MedKoo Cat#: 597042 | Name: Gallopamil, (-)-

Description:

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

Gallopamil, (-)- is an L-type calcium channel blocker that is an analog of verapamil. It is used in the treatment of abnormal heart rhythms.

Chemical Structure

Gallopamil, (-)-

CAS#36622-40-9 (free base - rotation)

Theoretical Analysis

MedKoo Cat#: 597042

Name: Gallopamil, (-)-

CAS#: 36622-40-9 (free base - rotation)

Chemical Formula: C28H40N2O5

Exact Mass: 484.2937

Molecular Weight: 484.63

Elemental Analysis: C, 69.39; H, 8.32; N, 5.78; O, 16.51

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 #

16662-47-8 (free base) 16662-46-7 (HCl) 36622-39-6 (HCl - rotation) 36622-40-9 (free base - rotation) 38176-09-9 (HCl + rotation) 38176-10-2(free base + rotation)

Synonym

Gallopamil, (-)-; (-)-Gallopamil; (-)-D 600; (-)-D600; (-)-D-600; (-)-Methoxyverapamil; (S)-Gallopamil;

IUPAC/Chemical Name

(S)-5-((3,4-dimethoxyphenethyl)(methyl)amino)-2-isopropyl-2-(3,4,5-trimethoxyphenyl)pentanenitrile

InChi Key

XQLWNAFCTODIRK-NDEPHWFRSA-N

InChi Code

InChI=1S/C28H40N2O5/c1-20(2)28(19-29,22-17-25(33-6)27(35-8)26(18-22)34-7)13-9-14-30(3)15-12-21-10-11-23(31-4)24(16-21)32-5/h10-11,16-18,20H,9,12-15H2,1-8H3/t28-/m0/s1

SMILES Code

N#C[C@](C(C)C)(CCCN(CCC1=CC=C(OC)C(OC)=C1)C)C2=CC(OC)=C(OC)C(OC)=C2

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 484.63 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.

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: Flores-Soto E, Reyes-García J, Carbajal-García A, Campuzano-González E, Perusquía M, Sommer B, Montaño LM. Sex steroids effects on guinea pig airway smooth muscle tone and intracellular Ca(2+) basal levels. Mol Cell Endocrinol. 2017 Jan 5;439:444-456. doi: 10.1016/j.mce.2016.10.004. Epub 2016 Oct 4. PubMed PMID: 27717744. 2: Grigorieva DV, Gorudko IV, Sokolov AV, Kostevich VA, Vasilyev VB, Cherenkevich SN, Panasenko OM. Myeloperoxidase Stimulates Neutrophil Degranulation. Bull Exp Biol Med. 2016 Aug;161(4):495-500. doi: 10.1007/s10517-016-3446-7. Epub 2016 Sep 6. PubMed PMID: 27597056. 3: Sumino K, Sheshadri A, Castro M. Calcium channel blocker reduces airway remodeling-or does it? Am J Respir Crit Care Med. 2015 Apr 15;191(8):863-4. doi: 10.1164/rccm.201502-0322ED. PubMed PMID: 25876196. 4: Aksoy-Aksel A, Manahan-Vaughan D. Synaptic strength at the temporoammonic input to the hippocampal CA1 region in vivo is regulated by NMDA receptors, metabotropic glutamate receptors and voltage-gated calcium channels. Neuroscience. 2015 Nov 19;309:191-9. doi: 10.1016/j.neuroscience.2015.03.014. Epub 2015 Mar 17. PubMed PMID: 25791230. 5: Girodet PO, Dournes G, Thumerel M, Begueret H, Dos Santos P, Ozier A, Dupin I, Trian T, Montaudon M, Laurent F, Marthan R, Berger P. Calcium channel blocker reduces airway remodeling in severe asthma. A proof-of-concept study. Am J Respir Crit Care Med. 2015 Apr 15;191(8):876-83. doi: 10.1164/rccm.201410-1874OC. PubMed PMID: 25633090. 6: St-Onge M, Dubé PA, Gosselin S, Guimont C, Godwin J, Archambault PM, Chauny JM, Frenette AJ, Darveau M, Le Sage N, Poitras J, Provencher J, Juurlink DN, Blais R. Treatment for calcium channel blocker poisoning: a systematic review. Clin Toxicol (Phila). 2014 Nov;52(9):926-44. doi: 10.3109/15563650.2014.965827. Epub 2014 Oct 6. Review. PubMed PMID: 25283255; PubMed Central PMCID: PMC4245158. 7: Szentandrássy N, Nagy D, Ruzsnavszky F, Harmati G, Bányász T, Magyar J, Szentmiklósi AJ, Nánási PP. Powerful technique to test selectivity of agents acting on cardiac ion channels: the action potential voltage-clamp. Curr Med Chem. 2011;18(24):3737-56. Review. PubMed PMID: 21774754. 8: Girodet PO, Ozier A, Bara I, Tunon de Lara JM, Marthan R, Berger P. Airway remodeling in asthma: new mechanisms and potential for pharmacological intervention. Pharmacol Ther. 2011 Jun;130(3):325-37. doi: 10.1016/j.pharmthera.2011.02.001. Epub 2011 Feb 17. Review. PubMed PMID: 21334378. 9: Hayashi S, Hester RK. Reduction in extracellular Ca2+ attenuates endothelium-dependent relaxation more than nitroprusside-induced relaxation. Acta Pharmacol Sin. 2010 Jan;31(1):19-26. doi: 10.1038/aps.2009.164. Epub 2009 Nov 16. PubMed PMID: 19915583; PubMed Central PMCID: PMC4002686. 10: Cheng RC, Tikhonov DB, Zhorov BS. Structural model for phenylalkylamine binding to L-type calcium channels. J Biol Chem. 2009 Oct 9;284(41):28332-42. doi: 10.1074/jbc.M109.027326. Epub 2009 Aug 21. PubMed PMID: 19700404; PubMed Central PMCID: PMC2788883. 11: Matsuoka H, Harada K, Ikeda T, Uetsuki K, Sata T, Warashina A, Inoue M. Ca2+ pathway involved in the refilling of store sites in rat adrenal medullary cells. Am J Physiol Cell Physiol. 2009 Apr;296(4):C889-99. doi: 10.1152/ajpcell.00439.2008. Epub 2009 Jan 28. PubMed PMID: 19176761. 12: Lorenz M, Hellige N, Rieder P, Kinkel HT, Trimpert C, Staudt A, Felix SB, Baumann G, Stangl K, Stangl V. Positive inotropic effects of epigallocatechin-3-gallate (EGCG) involve activation of Na+/H+ and Na+/Ca2+ exchangers. Eur J Heart Fail. 2008 May;10(5):439-45. doi: 10.1016/j.ejheart.2008.03.004. Epub 2008 Apr 10. PubMed PMID: 18406205. 13: Tarabova B, Lacinova L, Engel J. Effects of phenylalkylamines and benzothiazepines on Ca(v)1.3-mediated Ca2+ currents in neonatal mouse inner hair cells. Eur J Pharmacol. 2007 Nov 14;573(1-3):39-48. Epub 2007 Jul 4. PubMed PMID: 17651721. 14: Martelli A, Robbiano L, Grossi S, Mattioli F, Brambilla G. Formation of DNA-damaging N-nitroso compounds from the interaction of calcium-channel blockers with nitrite. Toxicology. 2007 Sep 5;238(2-3):211-5. Epub 2007 Jun 14. PubMed PMID: 17644234. 15: Makani S, Chesler M. Endogenous alkaline transients boost postsynaptic NMDA receptor responses in hippocampal CA1 pyramidal neurons. J Neurosci. 2007 Jul 11;27(28):7438-46. PubMed PMID: 17626204. 16: Stefanova ID, Argirova MD, Krustev AD. Influence of model melanoidins on calcium-dependent transport mechanisms in smooth muscle tissue. Mol Nutr Food Res. 2007 Apr;51(4):468-72. PubMed PMID: 17357983. 17: Pöschel B, Manahan-Vaughan D. Persistent (>24h) long-term depression in the dentate gyrus of freely moving rats is not dependent on activation of NMDA receptors, L-type voltage-gated calcium channels or protein synthesis. Neuropharmacology. 2007 Jan;52(1):46-54. Epub 2006 Aug 8. PubMed PMID: 16899259. 18: Ito T, Fujimura N, Omote K, Namiki A. A selective beta2-adrenergic agonist, terbutaline, improves sepsis-induced diaphragmatic dysfunction in the rat. Life Sci. 2006 Jul 24;79(9):905-12. Epub 2006 Apr 17. PubMed PMID: 16603198. 19: Ansar MM, Ansari M. Nitric oxide involvement in pancreatic beta cell apoptosis by glibenclamide. Nitric Oxide. 2006 Feb;14(1):39-44. Epub 2005 Oct 26. PubMed PMID: 16256381. 20: Belyavskaya NA. Changes in calcium signalling, gravitropism, and statocyte ultrastructure in pea roots induced by calcium channel blockers. J Gravit Physiol. 2004 Jul;11(2):P209-10. PubMed PMID: 16240511.