Imipramine supplier | CasNO.50-49-7

Name
IMIPRAMINE
EINECS
CAS No. 50-49-7
Article Data30
CAS DataBase
Density 1.041g/cm³
Solubility 18.23mg/L(24 oC)
Melting Point 174°C
Formula C19H24 N2
Boiling Point 403.1°Cat760mmHg
Molecular Weight 280.413
Flash Point 179.7°C
Transport Information
Appearance
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 NO_x.
Risk Codes
Molecular Structure
Hazard Symbols
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
PSA 6.48000
LogP 3.94000

Synthetic route

: 6829-98-7
imipramine N-oxide

: 50-49-7
impramine

Conditions

Conditions	Yield
With sodium tetrahydroborate In water at 50 - 60℃; chemoselective reaction;	96%

: 50-47-5
desipramine

: 124-38-9
carbon dioxide

: 50-49-7
impramine

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%

: 50-00-0
formaldehyd

: 2095-95-6
didesmethylimipramine

: 50-49-7
impramine

Conditions

Conditions	Yield
With formic acid In water at 100℃; for 1h; Eschweiler-Clark Amine Methylation; Microwave irradiation;	61%

: 59485-34-6
1,2-bis(2-bromophenyl)ethane

: 109-55-7
1-amino-3-(dimethylamino)propane

: 50-49-7
impramine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 110℃; Buchwald-Hartwig Coupling;	60%

: 67-56-1
methanol

: 50-47-5
desipramine

: 50-49-7
impramine

Conditions

Conditions	Yield
With rhodium(III) chloride hydrate; potassium tert-butylate at 150℃; for 60h; Sealed tube; High pressure;	49%

: 303-49-1
Clomipramine

A: 14171-67-6
clomipramine N-oxide

B: 50-49-7
impramine

C: 3-hydroxyimipramine

D: 3-hydroxyimipramine-N-oxide

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

: 494-19-9
9,10-dihydrodibenzazepine

: 50-49-7
impramine

Conditions

Conditions	Yield
With sodium amide; benzene und Erwaermen der Reaktionsloesung mit <3-Chlor-propyl>-dimethyl-amin;

: 494-19-9
9,10-dihydrodibenzazepine

: 109-54-6
3-(Dimethylamino)propyl chloride

: 50-49-7
impramine

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;

: 124-38-9
carbon dioxide

: [3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-trimethylsilanyl-amine

: 50-49-7
impramine

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;

: 50-47-5
desipramine

: 124-38-9
carbon dioxide

: 79-22-1
methyl chloroformate

: 50-49-7
impramine

Conditions

Conditions	Yield
Mechanism; multistep reaction; labelled with 11C;

...Expand

: 58-28-6
desipramine hydrochloride

: 50-49-7
impramine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (NH4)2SO4 / 110 °C 2: 2.) LiAlH4 / 1.) THF, -45 deg C - 60 deg C, 2.) 60 deg C, 10 min View Scheme

: 50-47-5
desipramine

: 50-49-7
impramine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 79 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating View Scheme

: 64-18-6
formic acid

: 50-47-5
desipramine

: 50-49-7
impramine

Conditions

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; 1,3-bis-(diphenylphosphino)propane; phenylsilane In dibutyl ether at 60℃; for 18h; Schlenk technique; Inert atmosphere;	92 %Chromat.

: 113-52-0
Imipramine hydrochloride

: 50-49-7
impramine

Conditions

Conditions	Yield
With sodium hydroxide In water

: 165602-94-8
Imipramine N-glucuronide

: 50-49-7
impramine

Conditions

Conditions	Yield
With hydrogenchloride In water at 90℃;

: 50-49-7
impramine

: 74-88-4
methyl iodide

: 16870-81-8
Trimethyl-imipramine Iodide

Conditions

Conditions	Yield
In diethyl ether at 20℃; for 20h;	98%

: 50-49-7
impramine

: 130-85-8
Pamoic acid

: imipramine pamoate

Conditions

Conditions	Yield
In ethyl acetate at 20 - 50℃; Solvent; Temperature;	96%

: 50-49-7
impramine

: (6-bromohexyl)dimethyl-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propyl]ammonium bromide

: C38H52N4O2(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetonitrile Heating;	90%

: 629-03-8
1 ,6-dibromohexane

: 50-49-7
impramine

: (6-bromo-hexyl)-[3-(10,11-dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-dimethyl-ammonium; bromide

Conditions

Conditions	Yield
at 20℃;	86%

: 50-49-7
impramine

: C19H16(2)H8N2

Conditions

Conditions	Yield
With deuterium In tetrahydrofuran for 36h; Glovebox; Inert atmosphere; regioselective reaction;	84%

: 50-49-7
impramine

: C19H16(2)H8N2

Conditions

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; deuterium In tetrahydrofuran at 55℃; under 750.075 Torr; for 22h; Inert atmosphere;	80%

: 50-49-7
impramine

: 74-88-4
methyl iodide

: 129344-89-4
imipramine methiodide

Conditions

Conditions	Yield
In butanone for 1h; Ambient temperature;	77%

: 772-33-8
Koshlands reagent I

: 50-49-7
impramine

: 2-((5-(3-(dimethylamino)propyl)-10,11-dihydro-5H-dibenzo[b,f]azepin-2-yl)methyl)-4-nitrophenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 48h;	73%

: 50-49-7
impramine

: C24H30N2O5S

: C43H54N4O5S

Conditions

Conditions	Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; sodium acetate In N,N-dimethyl-formamide at 20℃; for 16h; Irradiation; Inert atmosphere; diastereoselective reaction;	64%

: 50-49-7
impramine

: 21085-72-3
1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

: 86492-48-0
((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-[3-(10,11-dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-dimethyl-ammonium; chloride

Conditions

Conditions	Yield
With XAD-2 ion-exchange resin; sodium hydrogencarbonate In water; benzene for 72h; Ambient temperature;	55%

: 773837-37-9
sodium cyanide

: 50-49-7
impramine

A: 494-19-9
9,10-dihydrodibenzazepine

B: 2-((3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-(methyl)amino)acetonitrile

C: 2-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-4-(dimethylamino)butanenitrile

Conditions

Conditions	Yield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; acetic acid In acetonitrile at 20℃; for 24h; Irradiation; Sealed tube;	A 50% B 22% C 23%

...Expand

: potassium cyanide

: 50-49-7
impramine

A: 494-19-9
9,10-dihydrodibenzazepine

B: 2-((3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-(methyl)amino)acetonitrile

C: 2-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-4-(dimethylamino)butanenitrile

Conditions

Conditions	Yield
With 2-Picolinic acid; iron(III) chloride; tert-Butyl peroxybenzoate; 18-crown-6 ether In acetonitrile at 50℃; for 48h;	A 6% B 35% C 15%

...Expand

: 629-03-8
1 ,6-dibromohexane

: 50-49-7
impramine

: C44H60N4(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetonitrile Heating;	24%

: 50-49-7
impramine

A: 796-28-1
10-Hydroxyimipramine

B: 303-70-8
2-hydroxyimipramine

C: 94436-87-0
4-hydroxyimipramine

Conditions

Conditions	Yield
Stage #1: impramine With ethylenediaminetetraacetic acid trisodium salt; oxygen; manganese (II) acetate tetrahydrate; ascorbic acid In water pH=4; Udenfriend reaction; Stage #2: With ferrous(II) sulfate heptahydrate; ethylenediaminetetraacetic acid trisodium salt; oxygen In water at 45℃; for 2h; Udenfriend reaction;	A 2.56% B 1.46% C 3.47%

...Expand

: 50-49-7
impramine

: 3046-50-2
[14C]methanol

: C18(14)CH22N2O

Conditions

Conditions	Yield
With oxygen; palladium on activated charcoal for 24h; Ambient temperature;

: 50-49-7
impramine

: 50-47-5
desipramine

Conditions

Conditions	Yield
With D-glucose; corn steep liquor; S. aureus; peptone; yeast extract In water at 37℃; Product distribution; other reagents;
With oxygen; palladium on activated charcoal In methanol for 24h; Ambient temperature;
With pooled human liver microsomes; Tris buffer; NADPH; magnesium chloride at 37℃; pH=7.4; Enzyme kinetics;
With human hepatic CYP1A2; human hepatic CYP2C9; human hepatic CYP3A4 Enzymatic reaction;
Multi-step reaction with 2 steps 1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 1,2-dichloro-ethane / 1 h / Reflux 2: 2 h / Reflux View Scheme

: 50-49-7
impramine

: 144434-72-0
2,8-dibromoimipramine

Conditions

Conditions	Yield
With N-Bromosuccinimide; silica gel In dichloromethane at 18℃;

Imipramine Chemical Properties

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.

Imipramine Uses

Imipramine (CAS NO.50-49-7) is commonly used as antidepressants of tricyclic .

Imipramine 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.

Imipramine Consensus Reports

EPA Genetic Toxicology Program.

Imipramine 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 NO_x.

Product Name

IMIPRAMINE

Synthetic route

Imipramine Chemical Properties

Imipramine Uses

Imipramine Toxicity Data With Reference

Imipramine Consensus Reports

Imipramine Safety Profile

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