118909-22-1 Usage
Description
9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE is a compound with a unique biochemical and pharmacological profile, characterized by its low toxicity and lack of measurable liver toxicity in humans. It is a potential therapeutic agent for Alzheimer's disease, exhibiting cholinesterase inhibitory properties.
Used in Pharmaceutical Industry:
9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE is used as a potential Alzheimer's disease therapeutic for its low toxicity and cholinesterase inhibitory properties, offering a promising alternative to existing treatments.
Used in Alzheimer's Disease Research:
9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE is used as a research compound for studying its potential as a therapeutic agent for Alzheimer's disease, due to its similar profile to THA but with significantly reduced toxicity.
Originator
Velnacrine maleate SM 10.888,Hoechst-Roussel (Aventis) Sumitimo JPN
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 118909-22-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,8,9,0 and 9 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 118909-22:
(8*1)+(7*1)+(6*8)+(5*9)+(4*0)+(3*9)+(2*2)+(1*2)=141
141 % 10 = 1
So 118909-22-1 is a valid CAS Registry Number.
InChI:InChI=1/C13H14N2O.C4H4O4/c14-13-8-4-1-2-5-9(8)15-10-6-3-7-11(16)12(10)13;5-3(6)1-2-4(7)8/h1-2,4-5,11,16H,3,6-7H2,(H2,14,15);1-2H,(H,5,6)(H,7,8)/b;2-1-
