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MedKoo Cat#: 524824 | Name: CP-122721

Description:

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

CP-122721 is a NK1 receptor antagonist that possesses unique antidepressant, anxiolytic, and antiemetic properties. It is also a potent and selective substance P receptor antagonist.

Chemical Structure

CP-122721
CP-122721
CAS#145742-28-5

Theoretical Analysis

MedKoo Cat#: 524824

Name: CP-122721

CAS#: 145742-28-5

Chemical Formula: C20H23F3N2O2

Exact Mass: 380.1712

Molecular Weight: 380.40

Elemental Analysis: C, 63.15; H, 6.09; F, 14.98; N, 7.36; O, 8.41

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
CP-122721; CP122721; CP 122721; UNII-R7OYP6N58F.
IUPAC/Chemical Name
(2S,3S)-N-(2-methoxy-5-(trifluoromethoxy)benzyl)-2-phenylpiperidin-3-amine
InChi Key
ZIWFCOIGUNPHPM-HKUYNNGSSA-N
InChi Code
InChI=1S/C20H23F3N2O2/c1-26-18-10-9-16(27-20(21,22)23)12-15(18)13-25-17-8-5-11-24-19(17)14-6-3-2-4-7-14/h2-4,6-7,9-10,12,17,19,24-25H,5,8,11,13H2,1H3/t17-,19-/m0/s1
SMILES Code
COc1ccc(OC(F)(F)F)cc1CN[C@H]2CCCN[C@H]2c3ccccc3
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, not in water
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 380.40 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
1: Lelas S, Li YW, Wallace-Boone TL, Taber MT, Newton AE, Pieschl RL, Davis CD, Molski TF, Newberry KS, Parker MF, Gillman KW, Bronson JJ, Macor JE, Lodge NJ. NK1 receptor antagonism lowers occupancy requirement for antidepressant-like effects of SSRIs in the gerbil forced swim test. Neuropharmacology. 2013 Oct;73:232-40. doi: 10.1016/j.neuropharm.2013.05.038. Epub 2013 Jun 12. PubMed PMID: 23770339. 2: Nakamura A, Tanaka T, Imanishi A, Kawamoto M, Toyoda M, Mizojiri G, Tsukimi Y. Bidirectional regulation of human colonic smooth muscle contractility by tachykinin NK(2) receptors. J Pharmacol Sci. 2011;117(2):106-15. Epub 2011 Sep 23. PubMed PMID: 21946672. 3: Obach RS, Margolis JM, Logman MJ. In vitro metabolism of CP-122,721 ((2S,3S)-2-phenyl-3-[(5-trifluoromethoxy-2-methoxy)benzylamino]piperidine), a non-peptide antagonist of the substance P receptor. Drug Metab Pharmacokinet. 2007 Oct;22(5):336-49. PubMed PMID: 17965517. 4: Wallace-Boone TL, Newton AE, Wright RN, Lodge NJ, McElroy JF. Behavioral and pharmacological validation of the gerbil forced-swim test: effects of neurokinin-1 receptor antagonists. Neuropsychopharmacology. 2008 Jul;33(8):1919-28. Epub 2007 Oct 3. PubMed PMID: 17912250. 5: Fridén M, Gupta A, Antonsson M, Bredberg U, Hammarlund-Udenaes M. In vitro methods for estimating unbound drug concentrations in the brain interstitial and intracellular fluids. Drug Metab Dispos. 2007 Sep;35(9):1711-9. Epub 2007 Jun 25. PubMed PMID: 17591680. 6: Kamel A, Du Y, Colizza K, Prakash C. Metabolism and excretion of CP-122,721, a non-peptide antagonist of the neurokinin NK1 receptor, in dogs: identification of the novel cleaved product 5-trifluoromethoxy salicylic acid in plasma. Xenobiotica. 2007 May;37(5):559-78. PubMed PMID: 17523057. 7: Colizza K, Awad M, Kamel A. Metabolism, pharmacokinetics, and excretion of the substance P receptor antagonist CP-122,721 in humans: structural characterization of the novel major circulating metabolite 5-trifluoromethoxy salicylic acid by high-performance liquid chromatography-tandem mass spectrometry and NMR spectroscopy. Drug Metab Dispos. 2007 Jun;35(6):884-97. Epub 2007 Mar 14. PubMed PMID: 17360832. 8: Kamel A, Davis J, Potchoiba MJ, Prakash C. Metabolism, pharmacokinetics and excretion of a potent tachykinin NK1 receptor antagonist (CP-122,721) in rat: characterization of a novel oxidative pathway. Xenobiotica. 2006 Feb-Mar;36(2-3):235-58. PubMed PMID: 16702114. 9: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Jun;27(5):331-72. PubMed PMID: 16082422. 10: Herpfer I, Lieb K. Substance P receptor antagonists in psychiatry: rationale for development and therapeutic potential. CNS Drugs. 2005;19(4):275-93. Review. PubMed PMID: 15813642. 11: Cory W, Field K, Wu-Linhares D. Is it the method or the process-separating the causes of low recovery. Drug Dev Ind Pharm. 2004 Sep;30(8):891-9. PubMed PMID: 15521334. 12: Atobe M, Yamazaki N, Kibayashi C. Enantioselective synthesis of primary 1-(aryl)alkylamines by nucleophilic 1,2-addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein-coupled receptor ligands. J Org Chem. 2004 Aug 20;69(17):5595-607. PubMed PMID: 15307728. 13: Kan KK, Jones RL, Ngan MP, Rudd JA, Wai MK. Emetic action of the prostanoid TP receptor agonist, U46619, in Suncus murinus (house musk shrew). Eur J Pharmacol. 2003 Dec 15;482(1-3):297-304. PubMed PMID: 14660035. 14: Auais A, Adkins B, Napchan G, Piedimonte G. Immunomodulatory effects of sensory nerves during respiratory syncytial virus infection in rats. Am J Physiol Lung Cell Mol Physiol. 2003 Jul;285(1):L105-13. Epub 2003 Mar 14. PubMed PMID: 12639840. 15: Varty GB, Cohen-Williams ME, Hunter JC. The antidepressant-like effects of neurokinin NK1 receptor antagonists in a gerbil tail suspension test. Behav Pharmacol. 2003 Feb;14(1):87-95. PubMed PMID: 12576885. 16: Varty GB, Cohen-Williams ME, Morgan CA, Pylak U, Duffy RA, Lachowicz JE, Carey GJ, Coffin VL. The gerbil elevated plus-maze II: anxiolytic-like effects of selective neurokinin NK1 receptor antagonists. Neuropsychopharmacology. 2002 Sep;27(3):371-9. PubMed PMID: 12225694. 17: Smith BJ, Doran AC, McLean S, Tingley FD 3rd, O'Neill BT, Kajiji SM. P-glycoprotein efflux at the blood-brain barrier mediates differences in brain disposition and pharmacodynamics between two structurally related neurokinin-1 receptor antagonists. J Pharmacol Exp Ther. 2001 Sep;298(3):1252-9. PubMed PMID: 11504828. 18: King KA, Hu C, Rodriguez MM, Romaguera R, Jiang X, Piedimonte G. Exaggerated neurogenic inflammation and substance P receptor upregulation in RSV-infected weanling rats. Am J Respir Cell Mol Biol. 2001 Feb;24(2):101-7. PubMed PMID: 11159042. 19: Diemunsch P, Grélot L. Potential of substance P antagonists as antiemetics. Drugs. 2000 Sep;60(3):533-46. Review. PubMed PMID: 11030465. 20: Gesztesi Z, Scuderi PE, White PF, Wright W, Wender RH, D'Angelo R, Black LS, Dalby PL, MacLean D. Substance P (Neurokinin-1) antagonist prevents postoperative vomiting after abdominal hysterectomy procedures. Anesthesiology. 2000 Oct;93(4):931-7. PubMed PMID: 11020741.