L-733060 HCl | CAS#148687-76-7 | 148700-85-0 | NK1 receptor antagonist

MedKoo Cat#: 522621 | Name: L-733,060 HCl salt

Description:

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

L-733060 or L-733,060 is an orally active, non-peptide, selective antagonist for the NK1 receptor, binding with a Ki of 0.08nM. L-733,060 has antidepressant and anxiolytic effects in animal studies, and reduces both the dopamine release and neurotoxicity produced by methamphetamine and cocaine. It shows antiinflammatory and anti-hepatotoxic effects in animals, and counteracts the development of hyperalgesia following nerve injury.[15][16] It also has anticancer effects in a variety of in vitro models.

Chemical Structure

L-733,060 HCl salt

CAS#148687-76-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 522621

Name: L-733,060 HCl salt

CAS#: 148687-76-7 (HCl)

Chemical Formula: C20H20ClF6NO

Exact Mass:

Molecular Weight: 439.83

Elemental Analysis: C, 54.62; H, 4.58; Cl, 8.06; F, 25.92; N, 3.18; O, 3.64

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.

Bulk Inquiry

Related CAS #

148687-76-7 (HCl) 148700-85-0 (free base)

Synonym

L-733,060; L733,060; L 733,060; L-733060; L733060; L 733060; L-733060 HCl salt.

IUPAC/Chemical Name

(2S,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]oxy}-2-phenylpiperidine hydrochloride

InChi Key

DYEUTIUITGHIEO-APTPAJQOSA-N

InChi Code

InChI=1S/C20H19F6NO.ClH/c21-19(22,23)15-9-13(10-16(11-15)20(24,25)26)12-28-17-7-4-8-27-18(17)14-5-2-1-3-6-14;/h1-3,5-6,9-11,17-18,27H,4,7-8,12H2;1H/t17-,18-;/m0./s1

SMILES Code

FC(C1=CC(C(F)(F)F)=CC(CO[C@@H]2[C@H](C3=CC=CC=C3)NCCC2)=C1)(F)F.[H]Cl

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 439.83 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: Pansare SV, Paul EK. Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: application of an organocatalytic direct vinylogous aldol reaction. Org Biomol Chem. 2012 Mar 14;10(10):2119-25. doi: 10.1039/c2ob06644k. Epub 2012 Jan 31. PubMed PMID: 22294285. 2: Bilke JL, Moore SP, O'Brien P, Gilday J. Catalytic asymmetric synthesis of piperidines from pyrrolidine: concise synthesis of L-733,060. Org Lett. 2009 May 7;11(9):1935-8. doi: 10.1021/ol900366m. PubMed PMID: 19338290. 3: Davis FA, Ramachandar T. alpha-Amino 1,3-Dithioketal Mediated Asymmetric Synthesis of Piperidines (L-733,060) and Tetrahydrofuran Glycines. Tetrahedron Lett. 2008 Jan 28;49(5):870-872. PubMed PMID: 19180171; PubMed Central PMCID: PMC2344145. 4: Rosso M, Robles-Frías MJ, Coveñas R, Salinas-Martín MV, Muñoz M. The NK-1 receptor is expressed in human primary gastric and colon adenocarcinomas and is involved in the antitumor action of L-733,060 and the mitogenic action of substance P on human gastrointestinal cancer cell lines. Tumour Biol. 2008;29(4):245-54. doi: 10.1159/000152942. Epub 2008 Sep 9. PubMed PMID: 18781096. 5: Liu RH, Fang K, Wang B, Xu MH, Lin GQ. Concise asymmetric synthesis of (+)-CP-99,994 and (+)-L-733,060 via efficient construction of homochiral syn-1,2-diamines and syn-1,2-amino alcohols. J Org Chem. 2008 Apr 18;73(8):3307-10. doi: 10.1021/jo8002979. Epub 2008 Mar 11. PubMed PMID: 18331063. 6: Muñoz M, Rosso M, Pérez A, Coveñas R, Rosso R, Zamarriego C, Soult JA, Montero I. Antitumoral action of the neurokinin-1-receptor antagonist L-733,060 and mitogenic action of substance P on human retinoblastoma cell lines. Invest Ophthalmol Vis Sci. 2005 Jul;46(7):2567-70. PubMed PMID: 15980249. 7: Muñoz M, Rosso M, Pérez A, Coveñas R, Rosso R, Zamarriego C, Piruat JI. The NK1 receptor is involved in the antitumoural action of L-733,060 and in the mitogenic action of substance P on neuroblastoma and glioma cell lines. Neuropeptides. 2005 Aug;39(4):427-32. PubMed PMID: 15939468. 8: Muñoz M, Pérez A, Coveñas R, Rosso M, Castro E. Antitumoural action of L-733,060 on neuroblastoma and glioma cell lines. Arch Ital Biol. 2004 Mar;142(2):105-12. PubMed PMID: 15248566. 9: Huang PQ, Liu LX, Wei BG, Ruan YP. Asymmetric synthesis of (+)-L-733, 060 and (+)-CP-99, 994 based on a new chiral 3-piperidinol synthon. Org Lett. 2003 May 29;5(11):1927-9. Erratum in: Org Lett. 2004 May 27;6(11):1881. PubMed PMID: 12762688. 10: Bang R, Sass G, Kiemer AK, Vollmar AM, Neuhuber WL, Tiegs G. Neurokinin-1 receptor antagonists CP-96,345 and L-733,060 protect mice from cytokine-mediated liver injury. J Pharmacol Exp Ther. 2003 Apr;305(1):31-9. PubMed PMID: 12649350. 11: Seabrook GR, Shepheard SL, Williamson DJ, Tyrer P, Rigby M, Cascieri MA, Harrison T, Hargreaves RJ, Hill RG. L-733,060, a novel tachykinin NK1 receptor antagonist; effects in [Ca2+]i mobilisation, cardiovascular and dural extravasation assays. Eur J Pharmacol. 1996 Dec 12;317(1):129-35. PubMed PMID: 8982729. 12: Rupniak NM, Carlson E, Boyce S, Webb JK, Hill RG. Enantioselective inhibition of the formalin paw late phase by the NK1 receptor antagonist L-733,060 in gerbils. Pain. 1996 Sep;67(1):189-95. PubMed PMID: 8895247.