130073-98-2

Basic information

• Product Name: 9-amino-1,2,3,4-tetrahydroacridin-2-ol
• Synonyms: 2-acridinol, 9-amino-1,2,3,4-tetrahydro-
• CAS NO: 130073-98-2
• Molecular Formula: C₁₃H₁₄N₂O
• Molecular Weight: 214.2631
• Mol File: 130073-98-2.mol

Chemical Properties

• Boiling Point: 470.2°C at 760 mmHg
• Flash Point: 238.1°C
• Density: 1.315g/cm³
• Vapor Pressure: 1.21E-09mmHg at 25°C
• Refractive Index: 1.726
• CAS DataBase Reference: 9-amino-1,2,3,4-tetrahydroacridin-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 9-amino-1,2,3,4-tetrahydroacridin-2-ol(130073-98-2)
• EPA Substance Registry System: 9-amino-1,2,3,4-tetrahydroacridin-2-ol(130073-98-2)

Safety Data

• Hazardous Substances Data: 130073-98-2(Hazardous Substances Data)

Upstream product

• 1684-40-8 tacrine monohydrochloride 
• 202657-67-8 9-carboxamido-3,4-dihydro-1H-acridin-2-one ethylene acetal 
• 202657-68-9 2-Oxo-1,2,3,4-tetrahydro-acridine-9-carboxylic acid amide 
• 202657-69-0 2-Hydroxy-1,2,3,4-tetrahydro-acridine-9-carboxylic acid amide 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 202657-76-9 2-hydroxy-9-methoxycarbonylamino-1,2,3,4-tetrahydroacridine 
• 91-56-5 indole-2,3-dione 

Relevant articles and documents

Synthesis of 9-Amino-, 9-Aminomethyl-1,2,3,4-tetrahydro- And 1,2,3,4,5,6,7,8-Octahydroacridine Derivatives

This paper describes the synthesis of 9-amino-2- and 4-hydroxy- and 2,4-dihydroxy-1,2,3,4-tetrahydroacridines 2 and of 9-amlnomethyl-1,2,3,4-tetrahydro- and 1,2,3,4,5,6,7,8-octahydroacridines 3 starting from the corresponding 9-carboxamido derivatives. A

Metabolic disposition of tacrine in primary suspensions of rat hepatocyte and in single-pass perfused liver: In vitro/in vivo comparisons

1. Incubations of tacrine (1,2,3,4-tetrahydro-9-acridinamine monohydrochloride monohydrate, THA) with a primary suspension of rat hepatocytes for 2 min resulted in formation of the 1-hydroxy derivative as the major metabolite with smaller amounts of the 2- and 4-hydroxy metabolites. 2. Apparent V(max) and K(m) for THA metabolism were 12.4 ± 3.3 nmol/min/g liver and 0.98 ± 0.34 μM respectively. 3. Incubations of THA for longer time-periods (> 10 min) resulted in irreversible binding of THA-derived radioactivity to hepatocellular protein. The apparent maximal rate of irreversible binding (B(max)) was 76.7 ± 30.5 pmol equivalents bound/h/mg cell protein, whereas the apparent K(b) for binding was 2.8 ± 1.4 μM. 4. The kinetic parameters, V(max) and K(m), were used to predict steady-state extraction ratios (ER(SS)) for various THA input concentrations (C(in)) in single-pass perfused rat liver. At low input concentrations (0.72-0.85 μM; C(in) K(m)), ER(SS) of THA was approximately 1. For higher C(in) (14.05, 20.72, 20.88 μM; C(in) ≥ K(m)), the calculated ER(SS) was markedly decreased with 0.300, 0.296 and 0.261, respectively. 5. The intrinsic clearance of THA (Cl(i)) estimated from in vitro hepatocyte data was 6.7 ml/min/g liver while the apparent oral THA clearance (Cl(oral)) calculated from in vivo rat data was 6.6 ml/min/g liver.

Simultaneous determination of tacrine and 1-hydroxy-, 2-hydroxy-, and 4- hydroxytacrine in human plasma by high-performance liquid chromatography with fluorescence detection

An analytical method was developed for the simultaneous reversed-phase (cyano) high-performance liquid chromatographic determination with fluorescence detection of tacrine and 1-hydroxy-, 2-hydroxy-, and 4- hydroxytacrine in human plasma. Alkalinized human plasma samples were extracted with a mixture of chloroform/l-propanol (90:10, v/v). Extraction recoveries generally ranged from 68% to 83% for all four compounds and did not appear to be concentration dependent over the range examined. Calibration curves were constructed over the following ranges: 0.5-30.0 ng/mL for tacrine (THA) and 4-hydroxytacrine (4-OH-THA), 1.0-30.0 ng/mL for 2-hydroxytacrine (2-OH-THA), and 0.925-46.2 ng/mL for 1-hydroxytacrine (1-OH-THA). The intra- and interassay precision (RSD) for the quality control specimens analyzed during validation were ≤11.8% and ≤9.28%, respectively. The intra- and interassay accuracy (RE) for the quality control specimens analyzed during validation ranged from 14.1% to -7.5% and 12.1% to -3.33%, respectively, for all four compounds. The limit of quantitation was estimated as the level of the lowest concentration in the calibration curve for each compound based on acceptable interassay precision and accuracy statistics generated at this concentration. The sensitivity of the method was adequate for the determination of THA, 1-OH-THA, 2-OH-THA, and 4-OH-THA following oral administration of Cognex (40 mg single dose) to normal volunteers.

Hydroxy-1,2,3,4-tetrahydroaminoacridines, a process for their preparation and their use as medicaments

There are disclosed compounds having the formula I where, n is 1 or 2;, X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro or trifluoromethyl;, R is hydrogen, benzyl or alkanoyl of 2- 12 carbons, with the proviso that the group -OR may not be