Hydroxytacrine maleate (CAS 118909-22-1)

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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 :

pK_a: 13.47, pK_b: 9.11

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

PubChem CID :

5702293

Merck Index :

14: 1310006

SMILES :

C1CC(C2=C(C3=CC=CC=C3N=C2C1)N)O.C(=CC(=O)O)C(=O)O

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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: # 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

Rated 5 out of 5 by NZ 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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