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Basic Information
| CAS No.: | 50-49-7 |
|---|---|
| Name: | IMIPRAMINE |
| Molecular Structure: | |
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| Formula: | C19H24 N2 |
| Molecular Weight: | 280.413 |
| Synonyms: | 5H-Dibenz[b,f]azepine,5-[3-(dimethylamino)propyl]-10,11-dihydro- (7CI,8CI); 1-(3-Dimethylaminopropyl)-4,5-dihydro-2,3,6,7-dibenzazepine;5,6-Dihydro-N-[3-(dimethylamino)propyl]-11H-dibenz[b,e]azepine;5-(3-Dimethylaminopropyl)-10,11-dihydro-5H-dibenz[b,f]azepine; Antideprin;Berkomine; Cristalia; Imipramine; Melipramine; N-(3-Dimethylaminopropyl)-o-iminodibenzyl;N-(g-Dimethylaminopropyl)iminodibenzyl;NSC 169866; Org 2463; Prazepine; Sermonil |
| Density: | 1.041g/cm3 |
| Melting Point: | 174°C |
| Boiling Point: | 403.1°Cat760mmHg |
| Flash Point: | 179.7°C |
| Solubility: | 18.23mg/L(24 oC) |
| Safety: | A human poison by ingestion. An experimental poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: somnolence, hallucinations, distorted perceptions, changes in motor activity, ataxia (loss of muscle coordination), coma, nausea and vomiting, irritative dermatitis. An experimental teratogen by ingestion. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. |
| PSA: | 6.48000 |
| LogP: | 3.94000 |
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Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate In water at 50 - 60℃; chemoselective reaction; | 96% |
Conditions
| Conditions | Yield |
|---|---|
| With hydrogen In octane at 150℃; for 30h; Autoclave; | 89% |
| With hydrogen; tris(acetylacetonato)ruthenium(III); lithium chloride; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 140℃; for 24h; Autoclave; Inert atmosphere; | 83 %Chromat. |
| With proazaphosphatrane; 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 90℃; under 750.075 Torr; for 1h; Inert atmosphere; Schlenk technique; chemoselective reaction; | 99 %Spectr. |
- 876124-39-9
N'-(4-carbomethoxy)desimipramine
- 50-49-7
impramine
Conditions
| Conditions | Yield |
|---|---|
| With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Heating; | 79% |
Conditions
| Conditions | Yield |
|---|---|
| With formic acid In water at 100℃; for 1h; Eschweiler-Clark Amine Methylation; Microwave irradiation; | 61% |
Conditions
| Conditions | Yield |
|---|---|
| With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 110℃; Buchwald-Hartwig Coupling; | 60% |
Conditions
| Conditions | Yield |
|---|---|
| With rhodium(III) chloride hydrate; potassium tert-butylate at 150℃; for 60h; Sealed tube; High pressure; | 49% |
Conditions
| Conditions | Yield |
|---|---|
| With oxygen In methanol; phosphate buffer at 25 - 28℃; pH=7.4; Product distribution; Further Variations:; Reagents; Photolysis; UV-irradiation; | A 15% B 15% C 40% D 20% |
...Expand
Conditions
| Conditions | Yield |
|---|---|
| With sodium amide; benzene und Erwaermen der Reaktionsloesung mit <3-Chlor-propyl>-dimethyl-amin; |
Conditions
| Conditions | Yield |
|---|---|
| With sodium hydroxide; potassium carbonate DMSO 1.) room temp., 2 h, 2.) 110 deg C, 18 h; Yield given. Multistep reaction; | |
| With potassium hydroxide; ammonium acetate In toluene at 20℃; Heating / reflux; |
Conditions
| Conditions | Yield |
|---|---|
| With lithium aluminium tetrahydride 1.) THF, -45 deg C - 60 deg C, 2.) 60 deg C, 10 min; Yield given. Multistep reaction; |
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IMIPRAMINE
Chemistry
Molecular Structure of Imipramine (CAS NO.50-49-7):
Molecular Formula: C19H24N2
Molecular Weight: 280.41
IUPAC Name: 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-Dimethylpropan-1-amine
Synonyms of Imipramine (CAS NO.50-49-7): Imipramine ; Aurora ka-7708 ; 1-(3-Dimethylaminopropyl)-4,5-dihydro-2,3,6,7-dibenzazepine ; 10,11-Dihydro-5-(3-(dimethylamino)propyl)-5H-dibenz[b,f]azepine ; 2,2'-(3-Dimethylaminopropylimino)bibenzyl ; 2,2'-(3-Dimethylaminopropylimino)dibenzyl ; 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine ; 5-(3-(Dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine
CAS NO: 50-49-7
EINECS: 200-042-1
Mol File: 50-49-7.mol
Index of Refraction: 1.574
Surface Tension: 40.1 dyne/cm
Density: 1.041 g/cm3
Flash Point: 179.7 °C
Enthalpy of Vaporization: 65.43 kJ/mol
Boiling Point: 403.1 °C at 760 mmHg
Vapour Pressure: 1.04E-06 mmHg at 25°C
Properties: white or light yellow crystalline powder, no smell, taste and burning hemp.
Solubility: soluble in water, ethanol; almost insoluble in ether.
Uses
Imipramine (CAS NO.50-49-7) is commonly used as antidepressants of tricyclic .
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LDLo | intravenous | 20mg/kg (20mg/kg) | Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973. | |
| cat | LDLo | oral | 100mg/kg (100mg/kg) | Zentralblatt fuer Pharmazie, Pharmakotherapie und Laboratoriums-diagnostik. Vol. 114, Pg. 787, 1975. | |
| child | LD50 | oral | 40mg/kg (40mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: COMA | Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980. |
| child | LDLo | oral | 35mg/kg (35mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA CARDIAC: OTHER CHANGES | Schweizerische Medizinische Wochenschrift. Vol. 99, Pg. 1157, 1969. |
| child | TDLo | oral | 30mg/kg (30mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ATAXIA | American Journal of Diseases of Children. Vol. 130, Pg. 507, 1976. |
| dog | LDLo | intravenous | 45mg/kg (45mg/kg) | PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Bollettino Chimico Farmaceutico. Vol. 112, Pg. 601, 1973. |
| dog | LDLo | oral | 100mg/kg (100mg/kg) | "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 78, 1972. | |
| human | LD50 | oral | 40mg/kg (40mg/kg) | Proceedings of the European Society for the Study of Drug Toxicity. Vol. 6, Pg. 171, 1965. | |
| human | LDLo | oral | 450mg/kg (450mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE" | British Medical Journal. Vol. 1, Pg. 722, 1979. |
| mammal (species unspecified) | LD50 | oral | 350mg/kg (350mg/kg) | BEHAVIORAL: ANTICONVULSANT | Journal of Medicinal Chemistry. Vol. 8, Pg. 836, 1965. |
| mammal (species unspecified) | LD50 | unreported | 455mg/kg (455mg/kg) | Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 24(7), Pg. 27, 1990. | |
| man | LD50 | oral | 30mg/kg (30mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: COMA | Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980. |
| man | LDLo | oral | 71mg/kg (71mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: CHANGE IN RATE ENDOCRINE: CHANGE IN LH | Journal of Toxicology, Clinical Toxicology. Vol. 19, Pg. 239, 1982. |
| man | TDLo | oral | 5357ug/kg/5D- (5.357mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CHANGE IN REM SLEEP (HUMAN) | Human Psychopharmacology. Vol. 11, Pg. 211, 1996. |
| man | TDLo | oral | 8mg/kg/3D-I (8mg/kg) | BEHAVIORAL: EXCITEMENT | Lancet. Vol. 2, Pg. 568, 1959. |
| man | TDLo | oral | 71428ug/kg/10 (71.428mg/kg) | BEHAVIORAL: REGIDITY SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | Intensive Care Medicine. Vol. 23, Pg. 480, 1997. |
| mouse | LD50 | intraperitoneal | 51600ug/kg (51.6mg/kg) | British Patent Document. Vol. #1460700, | |
| mouse | LD50 | intravenous | 21mg/kg (21mg/kg) | AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: WAKEFULNESS | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 245, Pg. 283, 1980. |
| mouse | LD50 | oral | 188mg/kg (188mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Pharmaceutical Chemistry Journal Vol. 14, Pg. 773, 1980. |
| mouse | LD50 | subcutaneous | 195ug/kg (0.195mg/kg) | BEHAVIORAL: WAKEFULNESS | Pharmaceutical Chemistry Journal Vol. 15, Pg. 412, 1981. |
| mouse | LD50 | unreported | 107mg/kg (107mg/kg) | AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" | Journal of Medicinal Chemistry. Vol. 10, Pg. 418, 1967. |
| rabbit | LD50 | intravenous | 18mg/kg (18mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 120, Pg. 450, 1959. | |
| rabbit | LD50 | oral | 385mg/kg (385mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1617, 1969. | |
| rat | LD50 | intraperitoneal | 79mg/kg (79mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964. | |
| rat | LD50 | intravenous | 9300ug/kg (9.3mg/kg) | United States Patent Document. Vol. #4141993, | |
| rat | LD50 | oral | 250mg/kg (250mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Pharmaceutical Chemistry Journal Vol. 14, Pg. 773, 1980. |
| rat | LD50 | subcutaneous | 250mg/kg (250mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964. | |
| women | LDLo | oral | 2mg/kg/1D (2mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Journal of Pharmacy and Pharmacology. Vol. 16, Pg. 265, 1964. |
| women | TDLo | oral | 3mg/kg/32H-I (3mg/kg) | SKIN AND APPENDAGES (SKIN): PHOTOSENSITIVITY: AFTER SYSTEMIC EXPOSURE | JAMA, Journal of the American Medical Association. Vol. 254, Pg. 357, 1985. |
| women | TDLo | oral | 150mg/kg (150mg/kg) | BEHAVIORAL: COMA CARDIAC: OTHER CHANGES VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 51, 1995. |
Consensus Reports
EPA Genetic Toxicology Program.
Safety Profile
A human poison by ingestion. An experimental poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: somnolence, hallucinations, distorted perceptions, changes in motor activity, ataxia (loss of muscle coordination), coma, nausea and vomiting, irritative dermatitis. An experimental teratogen by ingestion. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.