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| CAS No.: | 321-64-2 |
|---|---|
| Name: | 1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE |
| Molecular Structure: | |
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|
|
| Formula: | C13H14 N2 |
| Molecular Weight: | 198.268 |
| Synonyms: | Acridine,9-amino-1,2,3,4-tetrahydro- (7CI,8CI); Acridine, 9-aminotetrahydro- (6CI);1,2,3,4-Tetrahydro-9-acridinamine; 1,2,3,4-Tetrahydro-9-aminoacridine;9-Amino-1,2,3,4-tetrahydroacridine; THA; Tacrine; Tetrahydroaminacrine;Tetrahydroaminocrin; Tetrahydroaminocrine |
| Density: | 1.195g/cm3 |
| Melting Point: | 183.5℃ |
| Boiling Point: | 409.4°Cat760mmHg |
| Flash Point: | 230.5°C |
| Hazard Symbols: |
 T
|
| Risk Codes: | R25; |
| Safety: | Poison by ingestion, intraperitoneal, and subcutaneous routes. Mutation data reported. Human systemic effects: changes in blood cell count, fatty degeneration, liver function tests impaired. When heated to decomposition it emits toxic fumes of NOx. |
| PSA: | 38.91000 |
| LogP: | 3.27700 |
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Chemistry
Product Name: Tetrahydroaminocrine (CAS NO.321-64-2)
Molecular Formula: C13H14N2
Molecular Weight: 198.26g/mol
Mol File: 321-64-2.mol
Einecs: 206-291-2
Boiling point: 409.4 °C at 760 mmHg
Flash Point: 230.5 °C
Density: 1.195 g/cm3
Surface Tension: 57.7 dyne/cm
Enthalpy of Vaporization: 66.16 kJ/mol
Vapour Pressure: 6.49E-07 mmHg at 25°C
XLogP3: 2.7
H-Bond Donor: 1
H-Bond Acceptor: 2
Uses
Tetrahydroaminocrine (CAS NO.321-64-2) is the central nervous system activity of physostigmine esterase drugs. It is mainly used to treat Alzheimer's disease.
Production
Aniline and hydroxylamine and chloral hydrate reaction, and then sulfuric acid catalyzed cyclization of isatin, the yield was 63.4%. Isatin, excess hydroxylamine hydrochloride, sodium acetate trihydrate and water, stirring at 60 °C after sharp overnight at room temperature. Filtration, ethanol - water, recrystallization, may isatin -3 - oxime, yield 92%. Isatin -3 - oxime is heated to melt, severe decomposition of o-amino-benzonitrile, using ether dissolved in the collection. After the vacuum distillation ether distilled product, the yield of 86.8%, boiling point 112 ~ 114 °C / 0.8kPa, melting point 48 ~ 50 °C. O-amino-benzonitrile dissolved in cyclohexanone by adding equimolar zinc chloride anhydrous 2, stirring to return. Cooling and filtering, the solid washed with ether several times, hanging in the water. Plus 30% sodium hydroxide Xeon alkaline, extracted with dichloromethane. Extract washing, drying, concentrated, using toluene recrystallization, may slightly yellow crystalline flakes of tacrine, the yield was 92.6%.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mammal (species unspecified) | LD50 | unreported | 31mg/kg (31mg/kg) | BEHAVIORAL: EUPHORIA BEHAVIORAL: ANTIPSYCHOTIC | Pharmaceutical Chemistry Journal Vol. 8, Pg. 409, 1974. |
| man | TDLo | oral | 176mg/kg/7W-I (176mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: LIVER FUNCTION TESTS IMPAIRED | Australian and New Zealand Journal of Medicine. Vol. 20, Pg. 193, 1990. |
| mouse | LD50 | intramuscular | 29mg/kg (29mg/kg) | Drugs of the Future. Vol. 15, Pg. 126, 1990. | |
| mouse | LD50 | intraperitoneal | 20mg/kg (20mg/kg) | Indian Journal of Pharmacology. Vol. 19, Pg. 44, 1987. | |
| mouse | LD50 | oral | 39800ug/kg (39.8mg/kg) | Journal of Medicinal Chemistry. Vol. 31, Pg. 1278, 1988. | |
| mouse | LD50 | subcutaneous | 25mg/kg (25mg/kg) | British Journal of Experimental Pathology. Vol. 28, Pg. 1, 1947. | |
| rat | LD50 | intramuscular | 34mg/kg (34mg/kg) | Drugs of the Future. Vol. 15, Pg. 126, 1990. | |
| rat | LD50 | intraperitoneal | 30mg/kg (30mg/kg) | Iugoslavica Physiologica et Pharmacologica Acta. Vol. 3, Pg. 43, 1967. | |
| rat | LD50 | oral | 70mg/kg (70mg/kg) | Journal of Medicinal Chemistry. Vol. 38, Pg. 2802, 1995. | |
| rat | LDLo | intravenous | 20mg/kg (20mg/kg) | United States Patent Document. Vol. #5409948, | |
| women | TDLo | oral | 84mg/kg/6W-I (84mg/kg) | LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" LIVER: LIVER FUNCTION TESTS IMPAIRED | Australian and New Zealand Journal of Medicine. Vol. 20, Pg. 193, 1990. |
| women | TDLo | oral | 294mg/kg/14W- (294mg/kg) | LIVER: FATTY LIVER DEGERATION LIVER: LIVER FUNCTION TESTS IMPAIRED BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) | Lancet. Vol. 1, Pg. 887, 1988. |
Safety Profile
Poison by ingestion, intraperitoneal, and subcutaneous routes. Mutation data reported. Human systemic effects: changes in blood cell count, fatty degeneration, liver function tests impaired. When heated to decomposition it emits toxic fumes of NOx.
Specification
Tetrahydroaminocrine ,its CAS NO. is 321-64-2,the synonyms is 1,2,3,4-Tetrahydro-5-aminoacridine ; 1,2,3,4-Tetrahydro-9-acridinamin ; 1,2,3,4-Tetrahydro-9-amino-acridin ; 1,2,3,4-Tetrahydro-9-aminoacridine ; 5-Amino-6,7,8,9-tetrahydroacridine ; Acridine, 1,2,3,4-tetrahydro-9-amino- ; Acridine, 9-amino-1,2,3,4-tetrahydro- ; Acridine, 9-aminotetrahydro- .