104628-20-8

Basic information

• Product Name: 9-(benzylamino)-6-fluoro-1,2,3,4-tetrahydroacridin-1-ol
• CAS NO: 104628-20-8
• Molecular Formula: C₂₀H₁₉FN₂O
• Molecular Weight: 322.3761
• Mol File: 104628-20-8.mol

Chemical Properties

• Boiling Point: 517.5°C at 760 mmHg
• Flash Point: 266.8°C
• Density: 1.316g/cm³
• Vapor Pressure: 1.55E-11mmHg at 25°C
• Refractive Index: 1.699
• CAS DataBase Reference: 9-(benzylamino)-6-fluoro-1,2,3,4-tetrahydroacridin-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(benzylamino)-6-fluoro-1,2,3,4-tetrahydroacridin-1-ol(104628-20-8)
• EPA Substance Registry System: 9-(benzylamino)-6-fluoro-1,2,3,4-tetrahydroacridin-1-ol(104628-20-8)

Safety Data

• Hazardous Substances Data: 104628-20-8(Hazardous Substances Data)

Upstream product

• 104586-66-5 9-benzylamino-3,4-dihydro-6-fluoroacridin-1(2H)-one 
• 104586-56-3 N-(3-oxo-cyclohexen-1-yl)-2-amino-4-fluorobenzonitrile 
• 104586-55-2 9-amino-3,4-dihydro-6-fluoroacridin-1(2H)-one 
• 80517-22-2 2-amino-4-fluorobenzonitrile 
• 504-02-9 1,3-cylohexanedione 
• 100-39-0 benzyl bromide 

Relevant articles and documents

9-Amino-1,2,3,4-tetrahydroacridin-1-ols: Synthesis and evaluation as potential Alzheimer's disease therapeutics

The synthesis of a series of 9-amino-1,2,3,4-tetrahydroacridin-1-ols is reported. These compounds are related to 1,2,3,4-tetrahydro-9-acridinamine (THA, tacrine). They inhibit acetylcholinesterase in vitro and are active in a model that may be predictive of activity in Alzheimer's disease - the scopolamine-induced impairment of 24-h memory of a passive dark-avoidance paradigm in mice. Two compounds, (±)-9-amino-1,2,3,4-tetrahydroacridin-1-ol maleate (1a, HP-029) and (±)-9-(benzylamino)-1,2,3,4-tetrahydroacridin-1-ol maleate (1p, HP-128), were also active in reversing the deficit in 72-h retention of a one-trial dark-avoidance task in rats, induced by ibotenic acid lesions in the nucleus basalis magnocellularis. In addition, compound 1p showed potent in vitro inhibition of the uptake of radiolabeled noradrenaline and dopamine (IC50 = 0.070 and 0.30 μM, respectively). Compounds 1a and 1p, which showed less acute toxicity in both rats and mice than THA, are in phase II and phase I clinical trials, respectively, for Alzheimer's disease.

9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds

There are disclosed compounds having the formula STR1 wherein n is 1, 2 or 3; X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, NHCOR2 where R2 is loweralkyl, or NR3 R4 where R3 and R4 are independently hydrogen or loweralkyl; R is hydrogen or loweralkyl; R1 is hydrogen, loweralkyl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, furylloweralkyl, thienylloweralkyl, oxygen-bridged arylloweralkyl, oxygen-bridged diarylloweralkyl, oxygen-bridged furylloweralkyl or oxygen-bridged thienylloweralkyl; Y is C=O or CR5 OH where R5 is hydrogen or loweralkyl; Z is CH2 or C=CR6 R7 where R6 and R7 are independently hydrogen or loweralkyl; or Y and Z taken together is CR5 =CH where CR5 and CH correspond to Y and Z respectively; an optical antipode thereof, or a pharmaceutically acceptable acid addition salt thereof, which are useful for enhancing memory, methods for synthesizing them, and pharmaceutical compositions comprising an effective memory enhancing amount of such a compound.