E-5842 (Citrate)

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

MedKoo CAT#: 530138

CAS#: 220120-14-9

Description: E-5842 (Citrate) is an opioid receptor agonist potentially for the treatment of psychotic disorders


Price and Availability

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E-5842 is not in stock, 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#: 530138
Name: E-5842 (Citrate)
CAS#: 220120-14-9
Chemical Formula: C23H29FN4O7
Exact Mass: 492.2
Molecular Weight: 492.5
Elemental Analysis: C, 56.09; H, 5.94; F, 3.86; N, 11.38; O, 22.74


Synonym: E-5842; E 5842; E5842

IUPAC/Chemical Name: 1-(4-(1H-1,2,4-triazol-1-yl)butyl)-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine 2-hydroxypropane-1,2,3-tricarboxylate

InChi Key: LTBKOSQVBVYJKW-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H21FN4.C6H8O7/c18-17-5-3-15(4-6-17)16-7-11-21(12-8-16)9-1-2-10-22-14-19-13-20-22;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-7,13-14H,1-2,8-12H2;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

SMILES Code: FC1=CC=C(C2=CCN(CCCCN3N=CN=C3)CC2)C=C1.O=C(CC(C(O)=O)(O)CC(O)=O)O


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

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


Additional Information

177945-17-9 (E-5842 Free Base)
220120-14-9(E-5842 Citrate )


References

1: Guzmán A, Marín AP, García C, Fernández de Henestrosa AR, Ruiz MT, Tortajada
A, Marcos R. Induction of hypothermic conditions associated with increased
micronuclei formation in sigma-1 receptor knockout mice after administration of
the antipsychotic compound E-5842. Environ Mol Mutagen. 2008 Dec;49(9):727-33.
doi: 10.1002/em.20428. PubMed PMID: 18800345.

2: Guzmán A, García C, Fernández de Henestrosa AR, Riley S, Ruiz MT, Marín AP,
Tortajada A. Assessment of the genotoxic potential of the antipsychotic sigma
receptor ligand E-5842. Mutat Res. 2006 Jun 16;605(1-2):63-77. PubMed PMID:
16677850.

3: Guzmán A, García C, Marín AP, Ruiz MT, Tortajada A, Fernández de Henestrosa
AR. Induction of micronuclei in mouse bone-marrow erythrocytes in association
with hypothermia after administration of the sigma receptor ligand E-5842. Mutat
Res. 2004 Dec 31;565(1):11-22. PubMed PMID: 15576235.

4: Romero G, Pérez MP, Carceller A, Monroy X, Farré AJ, Guitart X. Changes in
phosphoinositide signalling activity and levels of the alpha subunit of G(q/11)
protein in rat brain induced by E-5842, a sigma(1) receptor ligand and potential
atypical antipsychotic. Neurosci Lett. 2000 Sep 1;290(3):189-92. PubMed PMID:
10963895.

5: Ovalle S, Andreu F, Pérez MP, Zamanillo D, Guitart X. Effect of the novel
sigma1 receptor ligand and putative atypical antipsychotic E-5842 on BDNF mRNA
expression in the rat brain. Neuroreport. 2002 Dec 3;13(17):2345-8. PubMed PMID:
12488824.

6: Ovalle S, Zamanillo D, Andreu F, Farré AJ, Guitart X. Fibroblast growth
factor-2 is selectively modulated in the rat brain by E-5842, a preferential
sigma-1 receptor ligand and putative atypical antipsychotic. Eur J Neurosci. 2001
Mar;13(5):909-15. PubMed PMID: 11264663.

7: Beckett S. E-5842 (Laboratories Dr Esteve). IDrugs. 2000 Jun;3(6):666-8.
PubMed PMID: 16096930.

8: Sánchez-Arroyos R, Guitart X. Electrophysiological effects of E-5842, a sigma1
receptor ligand and potential atypical antipsychotic, on A9 and A10 dopamine
neurons. Eur J Pharmacol. 1999 Jul 28;378(1):31-7. PubMed PMID: 10478562.

9: Guitart X, Farré AJ. The effect of E-5842, a sigma receptor ligand and
potential atypical antipsychotic, on Fos expression in rat forebrain. Eur J
Pharmacol. 1998 Dec 18;363(2-3):127-30. PubMed PMID: 9881578.

10: Guzmán A, García C, Marín AP, Tortajada A, Ruiz MT, Fernández de Henestrosa
AR, Marcos R. Formation of micronucleated erythrocytes in mouse bone-marrow under
conditions of hypothermia is not associated with stimulation of erythropoiesis.
Mutat Res. 2008 Oct 30;656(1-2):8-13. doi: 10.1016/j.mrgentox.2008.06.016. PubMed
PMID: 18718553.

11: Monroy X, Romero G, Pérez MP, Farré AJ, Guitart X. Decrease of adenylyl
cyclase activity and expression by a sigma1 receptor ligand and putative atypical
antipsychotic. Neuroreport. 2001 Jul 3;12(9):1989-92. PubMed PMID: 11435935.

12: Guitart X, Méndez R, Ovalle S, Andreu F, Carceller A, Farré AJ, Zamanillo D.
Regulation of ionotropic glutamate receptor subunits in different rat brain areas
by a preferential sigma(1) receptor ligand and potential atypical antipsychotic.
Neuropsychopharmacology. 2000 Nov;23(5):539-46. PubMed PMID: 11027919.

13: Guzmán A, García C, Marín AP, Proudlock RJ, Fernández de Henestrosa AR, Ruiz
MT, Tortajada A, Lloyd M, Marcos R. Evaluation of the genotoxic potential of
three phenyltetrahydropyridinyl butylazole-derived sigma-receptor ligand drug
candidates. Mutat Res. 2008 May 31;653(1-2):91-8. doi:
10.1016/j.mrgentox.2008.03.011. PubMed PMID: 18502168.

14: Zamanillo D, Andreu F, Ovalle S, Pérez MP, Romero G, Farré AJ, Guitart X.
Up-regulation of sigma(1) receptor mRNA in rat brain by a putative atypical
antipsychotic and sigma receptor ligand. Neurosci Lett. 2000 Mar
24;282(3):169-72. PubMed PMID: 10717418.

15: Tweats DJ, Blakey D, Heflich RH, Jacobs A, Jacobsen SD, Morita T, Nohmi T,
O'Donovan MR, Sasaki YF, Sofuni T, Tice R; IWGT Working Group.. Report of the
IWGT working group on strategies and interpretation of regulatory in vivo tests
I. Increases in micronucleated bone marrow cells in rodents that do not indicate
genotoxic hazards. Mutat Res. 2007 Feb 3;627(1):78-91. PubMed PMID: 17116417.