L-733,060 HCl salt

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

MedKoo CAT#: 522621

CAS#: 148687-76-7 (HCl)

Description: 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.


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25mg
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2g
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500mg
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5g
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L-733,060 HCl salt is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 522621
Name: L-733,060 HCl salt
CAS#: 148687-76-7 (HCl)
Chemical Formula: C20H20ClF6NO
Exact Mass:
Molecular Weight: 439.8264
Elemental Analysis: C, 54.62; H, 4.58; Cl, 8.06; F, 25.92; N, 3.18; O, 3.64


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


Technical Data

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).

Harmonized System Code:
293490


References

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.