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MedKoo Cat#: 562004 | Name: N-Desmethyl Loperamide

Description:

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

N-Desmethyl Loperamide is the major metabolite of loperamide. It is also used as the precusor for radiolabelled loperamide.

Chemical Structure

N-Desmethyl Loperamide
N-Desmethyl Loperamide
CAS#66164-07-6

Theoretical Analysis

MedKoo Cat#: 562004

Name: N-Desmethyl Loperamide

CAS#: 66164-07-6

Chemical Formula: C28H31ClN2O2

Exact Mass: 462.2074

Molecular Weight: 463.01

Elemental Analysis: C, 72.63; H, 6.75; Cl, 7.66; N, 6.05; O, 6.91

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 #
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Synonym
N-Desmethyl Loperamide; dLop; R 20905; R-20905; R20905;
IUPAC/Chemical Name
4-(4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl)-N-methyl-2,2-diphenylbutanamide
InChi Key
ZMOPTLXEYOVARP-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H31ClN2O2/c1-30-26(32)28(23-8-4-2-5-9-23,24-10-6-3-7-11-24)18-21-31-19-16-27(33,17-20-31)22-12-14-25(29)15-13-22/h2-15,33H,16-21H2,1H3,(H,30,32)
SMILES Code
O=C(NC)C(C1=CC=CC=C1)(C2=CC=CC=C2)CCN3CCC(O)(C4=CC=C(Cl)C=C4)CC3
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

Preparing Stock Solutions

The following data is based on the product molecular weight 463.01 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: Vaz RJ, Kang J, Luo Y, Rampe D. Molecular determinants of loperamide and N-desmethyl loperamide binding in the hERG cardiac K(+) channel. Bioorg Med Chem Lett. 2017 Dec 15. pii: S0960-894X(17)31181-2. doi: 10.1016/j.bmcl.2017.12.020. [Epub ahead of print] PubMed PMID: 29274816. 2: Bhatti Z, Norsworthy J, Szombathy T. Loperamide metabolite-induced cardiomyopathy and QTc prolongation. Clin Toxicol (Phila). 2017 Aug;55(7):659-661. doi: 10.1080/15563650.2017.1304555. Epub 2017 Mar 28. PubMed PMID: 28349724. 3: Damont A, Goutal S, Auvity S, Valette H, Kuhnast B, Saba W, Tournier N. Imaging the impact of cyclosporin A and dipyridamole on P-glycoprotein (ABCB1) function at the blood-brain barrier: A [(11)C]-N-desmethyl-loperamide PET study in nonhuman primates. Eur J Pharm Sci. 2016 Aug 25;91:98-104. doi: 10.1016/j.ejps.2016.06.005. Epub 2016 Jun 7. PubMed PMID: 27283486. 4: Wanek T, Römermann K, Mairinger S, Stanek J, Sauberer M, Filip T, Traxl A, Kuntner C, Pahnke J, Bauer F, Erker T, Löscher W, Müller M, Langer O. Factors Governing P-Glycoprotein-Mediated Drug-Drug Interactions at the Blood-Brain Barrier Measured with Positron Emission Tomography. Mol Pharm. 2015 Sep 8;12(9):3214-25. doi: 10.1021/acs.molpharmaceut.5b00168. Epub 2015 Aug 3. PubMed PMID: 26202880; PubMed Central PMCID: PMC4566129. 5: Kreisl WC, Bhatia R, Morse CL, Woock AE, Zoghbi SS, Shetty HU, Pike VW, Innis RB. Increased permeability-glycoprotein inhibition at the human blood-brain barrier can be safely achieved by performing PET during peak plasma concentrations of tariquidar. J Nucl Med. 2015 Jan;56(1):82-7. doi: 10.2967/jnumed.114.146894. Epub 2014 Dec 11. PubMed PMID: 25500831; PubMed Central PMCID: PMC4495896. 6: Wanek T, Mairinger S, Langer O. Radioligands targeting P-glycoprotein and other drug efflux proteins at the blood-brain barrier. J Labelled Comp Radiopharm. 2013 Mar-Apr;56(3-4):68-77. doi: 10.1002/jlcr.2993. Review. PubMed PMID: 24285312. 7: Wang M, Gao M, Zheng QH. A high-yield route to synthesize the P-glycoprotein radioligand [11C]N-desmethyl-loperamide and its parent radioligand [11C]loperamide. Bioorg Med Chem Lett. 2013 Oct 1;23(19):5259-63. doi: 10.1016/j.bmcl.2013.08.024. Epub 2013 Aug 13. PubMed PMID: 23981899. 8: Farwell MD, Chong DJ, Iida Y, Bae SA, Easwaramoorthy B, Ichise M. Imaging P-glycoprotein function in rats using [(11)C]-N-desmethyl-loperamide. Ann Nucl Med. 2013 Aug;27(7):618-24. doi: 10.1007/s12149-013-0725-5. Epub 2013 Apr 10. PubMed PMID: 23572210. 9: Sugimoto H, Hirabayashi H, Amano N, Moriwaki T. Retrospective analysis of P-glycoprotein-mediated drug-drug interactions at the blood-brain barrier in humans. Drug Metab Dispos. 2013 Apr;41(4):683-8. doi: 10.1124/dmd.112.049577. Epub 2013 Jan 22. PubMed PMID: 23340958. 10: Zamek-Gliszczynski MJ, Bedwell DW, Bao JQ, Higgins JW. Characterization of SAGE Mdr1a (P-gp), Bcrp, and Mrp2 knockout rats using loperamide, paclitaxel, sulfasalazine, and carboxydichlorofluorescein pharmacokinetics. Drug Metab Dispos. 2012 Sep;40(9):1825-33. doi: 10.1124/dmd.112.046508. Epub 2012 Jun 18. PubMed PMID: 22711747. 11: Moerman L, Dumolyn C, Boon P, De Vos F. The influence of mass of [11C]-laniquidar and [11C]-N-desmethyl-loperamide on P-glycoprotein blockage at the blood-brain barrier. Nucl Med Biol. 2012 Jan;39(1):121-5. doi: 10.1016/j.nucmedbio.2011.06.009. Epub 2011 Sep 29. PubMed PMID: 21958857. 12: Moerman L, Wyffels L, Slaets D, Raedt R, Boon P, De Vos F. Antiepileptic drugs modulate P-glycoproteins in the brain: a mice study with (11)C-desmethylloperamide. Epilepsy Res. 2011 Mar;94(1-2):18-25. doi: 10.1016/j.eplepsyres.2010.12.013. Epub 2011 Jan 31. PubMed PMID: 21277169. 13: Kannan P, Brimacombe KR, Kreisl WC, Liow JS, Zoghbi SS, Telu S, Zhang Y, Pike VW, Halldin C, Gottesman MM, Innis RB, Hall MD. Lysosomal trapping of a radiolabeled substrate of P-glycoprotein as a mechanism for signal amplification in PET. Proc Natl Acad Sci U S A. 2011 Feb 8;108(6):2593-8. doi: 10.1073/pnas.1014641108. Epub 2011 Jan 24. PubMed PMID: 21262843; PubMed Central PMCID: PMC3038699. 14: Leung K. [N-methyl-(11)C]4-(4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl)-2,2-diphenyl-N-met hyl-butanamide. 2009 May 2 [updated 2009 Dec 3]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK23105/ PubMed PMID: 20641310. 15: Seneca N, Zoghbi SS, Shetty HU, Tuan E, Kannan P, Taku A, Innis RB, Pike VW. Effects of ketoconazole on the biodistribution and metabolism of [11C]loperamide and [11C]N-desmethyl-loperamide in wild-type and P-gp knockout mice. Nucl Med Biol. 2010 Apr;37(3):335-45. doi: 10.1016/j.nucmedbio.2009.12.010. PubMed PMID: 20346873; PubMed Central PMCID: PMC2847595. 16: Kreisl WC, Liow JS, Kimura N, Seneca N, Zoghbi SS, Morse CL, Herscovitch P, Pike VW, Innis RB. P-glycoprotein function at the blood-brain barrier in humans can be quantified with the substrate radiotracer 11C-N-desmethyl-loperamide. J Nucl Med. 2010 Apr;51(4):559-66. doi: 10.2967/jnumed.109.070151. Epub 2010 Mar 17. PubMed PMID: 20237038; PubMed Central PMCID: PMC2856602. 17: Kannan P, Brimacombe KR, Zoghbi SS, Liow JS, Morse C, Taku AK, Pike VW, Halldin C, Innis RB, Gottesman MM, Hall MD. N-desmethyl-loperamide is selective for P-glycoprotein among three ATP-binding cassette transporters at the blood-brain barrier. Drug Metab Dispos. 2010 Jun;38(6):917-22. doi: 10.1124/dmd.109.031161. Epub 2010 Mar 8. PubMed PMID: 20212014; PubMed Central PMCID: PMC2879961. 18: Seneca N, Zoghbi SS, Liow JS, Kreisl W, Herscovitch P, Jenko K, Gladding RL, Taku A, Pike VW, Innis RB. Human brain imaging and radiation dosimetry of 11C-N-desmethyl-loperamide, a PET radiotracer to measure the function of P-glycoprotein. J Nucl Med. 2009 May;50(5):807-13. doi: 10.2967/jnumed.108.058453. Epub 2009 Apr 16. PubMed PMID: 19372478; PubMed Central PMCID: PMC2792991. 19: Liow JS, Kreisl W, Zoghbi SS, Lazarova N, Seneca N, Gladding RL, Taku A, Herscovitch P, Pike VW, Innis RB. P-glycoprotein function at the blood-brain barrier imaged using 11C-N-desmethyl-loperamide in monkeys. J Nucl Med. 2009 Jan;50(1):108-15. doi: 10.2967/jnumed.108.056226. Epub 2008 Dec 17. PubMed PMID: 19091890; PubMed Central PMCID: PMC2652692. 20: Lazarova N, Zoghbi SS, Hong J, Seneca N, Tuan E, Gladding RL, Liow JS, Taku A, Innis RB, Pike VW. Synthesis and evaluation of [N-methyl-11C]N-desmethyl-loperamide as a new and improved PET radiotracer for imaging P-gp function. J Med Chem. 2008 Oct 9;51(19):6034-43. doi: 10.1021/jm800510m. Epub 2008 Sep 11. PubMed PMID: 18783208; PubMed Central PMCID: PMC2646255.

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