ChemicalBook > CAS DataBase List > 9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE

9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE

Product Name
9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE
CAS No.
118909-22-1
Chemical Name
9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE
Synonyms
HP-029;Mentane;P 83-6029A;Velnacrine maleate;HYDROXYTACRINE MALEATE;Velnacrine maleate [usan];1-hydroxy tacrine Maleate;Velnacrine Maleate(HP-029);HYDROXYTACRINE MALEATE SALT;Velnacrine Hydrogen Maleate
CBNumber
CB7187399
Molecular Formula
C17H18N2O5
Formula Weight
330.34
MOL File
118909-22-1.mol
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9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE Property

Melting point:
171-173
storage temp. 
Sealed in dry,2-8°C
solubility 
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form 
White solid.
color 
Pale Beige to Beige
Stability:
Store in freezer at -20°C
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Safety

Hazard Codes 
T
Hazard Note 
Toxic
HS Code 
2933998090
Toxicity
LD50 in mice (mg/kg): 136 orally; 162 i.p. (Shutske 1988, 1989)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Alfa Aesar
Product number
J60680
Product name
Hydroxytacrine maleate salt
Packaging
250mg
Price
$72.65
Updated
2024/03/01
Alfa Aesar
Product number
J60680
Product name
Hydroxytacrine maleate salt
Packaging
1g
Price
$249
Updated
2021/12/16
Cayman Chemical
Product number
18508
Product name
Hydroxytacrine (maleate)
Purity
≥98%
Packaging
100mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
18508
Product name
Hydroxytacrine (maleate)
Purity
≥98%
Packaging
1g
Price
$283
Updated
2024/03/01
Cayman Chemical
Product number
18508
Product name
Hydroxytacrine (maleate)
Purity
≥98%
Packaging
250mg
Price
$86
Updated
2024/03/01
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9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE Chemical Properties,Usage,Production

Originator

Velnacrine maleate SM 10.888,Hoechst-Roussel (Aventis) Sumitimo JPN

Uses

Cholinesterase inhibitor. Potential Alzheimer's disease therapeutic

Uses

A potential Alzheimer Disease therapeutic of low toxicity. Exhibits biochemical and pharmacological profile similar to THA except that it is far less toxic and without measurable liver toxicity in humans

Uses

A potential Alzheimer's Disease therapeutic of low toxicity. Exhibits biochemical and pharmacological profile similar to THA except that it is far less toxic and without measurable liver toxicity in humans.

Manufacturing Process

In 100 ml of tetrahydrofuran was added 5.00 g of 9-amino-3,4-dihydroacridin- 1(2)-one. The mechanically stirred suspension was cooled to -5°C and 21.4 ml (1 eq.) of 1.1 M LiAlH 4 solution in ether was added dropwise. After completion of the addition, the reaction mixture was stirred further for 2 hours, whereupon the reaction complete based on thin chromatography analysis. The LiAlH 4 was neutralized with 2 ml of saturated NH 4 Cl and the salts were dissolved with 30% potassium hydroxide. The insoluble product was filtered off and rinsed with water. The precipitate was then dissolved in 3 N hydrochloric acid and the residual insoluble salts filtered off. The acid solution washed with ethyl acetate and made basic (pH 9) with 10% sodium hydroxide. The precipitated product was filtered and washed with water. After drying at 80°C under vacuum overnight, 4.15 g (82%) of (+/-)-9-amino- 1,2,3,4-tetrahydro-1-acridinol was obtained, melting point 245°C. (+/-)-9- Amino-1,2,3,4-tetrahydro-1-acridinol maleate has melting point 171-173°C.

brand name

Mentane (Hoechst-Roussel).

Therapeutic Function

Cholinesterase inhibitor, Cognition activator

Biological Activity

hydroxytacrine maleate, a bioactive monohydroxylated metabolite of cholinesterase inhibitor, is a potential alzheimer's therapeutic of low toxicity [1]. hydroxytacrine maleate exhibited biochemical and pharmacological profile similar to tacrine (tha) except that the far less liver toxicity in humans. the prolonged use of tacrine has been associated with liver toxicity[1, 2].hydroxytacrine maleate is a parasympathomimetic and a centrally acting cholinesterase inhibitor (anticholinesterase). as the first cholinesterase inhibitor approved for the treatment of ad, tacrine was marketed under the trade name cognex [3]. through hydroxylation of benzylic carbon by cyp450 in the liver, tacrine has been metabolized into metabolite 1-hydroxy-tacrine (velnacrine) [4]. it has also been shown that maleate is an inhibitor of ache [5].

References

[1]. d. muoz-torrero. acetylcholinesterase inhibitors as disease-modifying therapies for alzheimer’s disease. curr. med. chem. 15, 2433-2455 (2008).
[2]. e. giacobini. cholinesterase inhibitors for alzheimer’s disease therapy: from tacrine to future applications. neurochemistry international 32, 413-419(1998).
[3]. birks j s. cholinesterase inhibitors for alzheimer's disease[j]. the cochrane library, 2006.
[4]. peng j z, remmel r p, sawchuk r j. inhibition of murine cytochrome p4501a by tacrine: in vitro studies[j]. drug metabolism and disposition, 2004, 32(8): 805-812.
[5]. acetylcholine and choline effects on erythrocyte nitrite and nitrate levels.

9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE Preparation Products And Raw materials

Raw materials

Preparation Products

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9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE Suppliers

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118909-22-1, 9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATERelated Search:


  • HP-029
  • HYDROXYTACRINE MALEATE
  • HYDROXYTACRINE MALEATE SALT
  • 9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDINE-1-(2H)-OL MALEATE
  • 9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE
  • (±)-9-Amino-1,2,3,4-tetrahydroacridin-1-ol, HP-029
  • Velnacrine maleate
  • Velnacrine maleate [usan]
  • Velnacrine Maleate(HP-029)
  • 1-hydroxy tacrine Maleate
  • 9-AMino-1,2,3,4-tetrahydro-1-acridinol (2Z)-2-Butenedioate
  • Mentane
  • P 83-6029A
  • Velnacrine Hydrogen Maleate
  • 9-Amino-1,2,3,4-tetrahydroacridin-1-ol maleate, 9-Amino-1,2,3,4-tetrahydroacridin-1-ol (2Z)-but-2-enedioate
  • 9-Amino-1-hydroxy-1,2,3,4-tetrahydroacridine maleate
  • Velnacrine maleate|||HP 029 maleate
  • 118909-22-1
  • C13H14N2OC4H4O4
  • Amines
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Cholinergics
  • Heterocyclic Compounds
  • Neurochemicals