Hydroxytacrine maleate CAS: 118909-22-1
MF: C13H14N2O•C4H4O4
MW: 330.3
A cholinesterase inhibitor that exhibits a biochemical profile very similar to tacrine.

Hydroxytacrine maleate (CAS 118909-22-1)

Hydroxytacrine maleate | CAS 118909-22-1 is rated 5.0 out of 5 by 1.
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Alternate Names: 9-amino-1,2,3,4-tetrahydroacridin-1-ol maleate
Application: A cholinesterase inhibitor that exhibits a biochemical profile very similar to tacrine
CAS Number: 118909-22-1
Purity: 98%
Molecular Weight: 330.3
Molecular Formula: C13H14N2O•C4H4O4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Hydroxytacrine maleate is a cholinesterase inhibitor and a potential Alzheimer's therapeutic of low toxicity. Exhibits biochemical and pharmacological profile similar to tacrine (THA) except that it is far less toxic and without measurable liver toxicity in humans. Tacrine is a parasympathomimetic and a centrally acting cholinesterase inhibitor (anticholinesterase). It was the first centrally-acting cholinesterase inhibitor approved for the treatment of Alzheimer's disease, and was marketed under the trade name Cognex. Major form of metabolism is in the liver via hydroxylation of benzylic carbon by CYP450. This forms the major metabolite 1-hydroxy-tacrine (velnacrine) which is still active. Hydroxytacrine maleate is an inhibitor of AChE.


References

1. Shutske, G.M., et al. 1988. J. Med. Chem. 31: 1278-1279. PMID: 3385720
2. Alon, R., et al. 1995. J. Cell Biol. 128: 1243-1253. PMID: 7534768
3. Min, W. and Pober, J.S. 1997. J. Immunol. 159: 3508-3518. PMID: 9317150
4. Lum, A.F., et al. 2002. J. Biol. Chem. 277: 20660-20670. PMID: 11929876
5. Carvalho, F.A., et al. 2004. J Appl Toxicol. 24: 419-427. PMID: 15551380

Physical State :
Solid
Solubility :
Soluble in water (5 mg/mL warm), DMSO (25 mg/mL), and ethanol (10 mg/mL).
Storage :
Store at -20° C
Melting Point :
171-173° C
IC50 :
Acetylcholinesterase: IC50 = 4800 nM (Rattus norvegicus)
pK Values :
pKa: 13.47, pKb: 9.11
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
Merck Index :
14: 1310006
SMILES :
C1CC(C2=C(C3=CC=CC=C3N=C2C1)N)O.C(=CC(=O)O)C(=O)O

Download SDS (MSDS)

Certificate of Analysis

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Hydroxytacrine maleate (CAS 118909-22-1)  Product Citations

See how others have used Hydroxytacrine maleate (CAS 118909-22-1). Click on the entry to view the PubMed entry .

Citations 1 to 8 of 8 total

PMID: # 30257601  Liederer, BM.|Cheong, J.|Chou, KJ.|Dragovich, PS.|Le, H.|Liang, X.|Ly, J.|Mukadam, S.|Oeh, J.|Sampath, D.|Wang, L.|Wong, S.| et al. 2019. Xenobiotica. 49: 1063-1077.

PMID: # 29127322  Donkers, JM. et al. 2017. Sci Rep. 7: 15307.

PMID: # 25269881  Lau, CG. et al. 2014. Mol. Reprod. Dev. 81: 994-1008.

PMID: # 19101643  Lopes de Almeida, JP. et al. 2009. Cell Biol. Int. 33: 268-275.

PMID: # 7480518  Jackson, WJ. et al. 1995. Psychopharmacology (Berl.). 119: 391-398.

PMID: # 7648773  Clipp, EC. et al. 1995. Clin. Pharmacol. Ther. 58: 228-236.

PMID: # 1410128  Ebmeier, KP. et al. 1992. Psychopharmacology (Berl.). 108: 103-109.

PMID: # 1468493  Bosch, F. et al. 1992. Eur. J. Pharmacol. 222: 163-166.

Citations 1 to 8 of 8 total
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Rated 5 out of 5 by from Ebmeier et al Ebmeier et al. (PubMed ID 1410128) used Hydroxytacrine maleate to inhibit acetycholinerase in patients with Alzheimer s disease. -SCBT Publication Review
Date published: 2015-06-27
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