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Substance Name: Imipramine [INN:BAN]
RN: 50-49-7
UNII: OGG85SX4E4
InChIKey: BCGWQEUPMDMJNV-UHFFFAOYSA-N

Note

  • The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.

Molecular Formula

  • C19-H24-N2

Molecular Weight

  • 280.413
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Uptake Inhibitors
  • Antidepressive Agents
  • Antidepressive Agents, Tricyclic
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Mutation Data
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Psychotropic Drugs
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Imipramine
  • Imipramine [INN:BAN]

MeSH Heading

  • Imipramine

Synonyms

  • 1-(3-Dimethylaminopropyl)-4,5-dihydro-2,3,6,7-dibenzazepine
  • 2,2'-(3-Dimethylaminopropylimino)bibenzyl
  • 2,2'-(3-Dimethylaminopropylimino)dibenzyl
  • 5,6-Dihydro-N-(3-(dimethylamino)propyl)-11H-dibenz(b,e)azepine
  • 5-(3-(Dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine
  • 5-(3-Dimethylaminopropyl)-10,11-dihydro-5H-dibenzo(b,f)azepine
  • 5-20-08-00096 (Beilstein Handbook Reference)
  • 5H-Dibenz(b,f)azepine, 10,11-dihydro-5-(3-(dimethylamino)propyl)-
  • 5H-Dibenz(b,f)azepine, 5-(3-(dimethylamino)propyl)-10,11-dihydro-
  • 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-
  • Antideprin
  • Berkomine
  • BRN 0256892
  • CCRIS 9173
  • Censtim
  • Censtin
  • Dimipressin
  • Dpid
  • Dyna-zina
  • Dynaprin
  • EINECS 200-042-1
  • HSDB 3100
  • Imidobenzyle
  • Imipramina
  • Imipramina [INN-Spanish]
  • Imipramina [Italian]
  • Imipramine
  • Imipraminum
  • Imipraminum [INN-Latin]
  • Imiprin
  • Impramine
  • Intalpram
  • Iramil
  • Irmin
  • Janimine
  • Melipramin
  • Melipramine
  • N-(3-Dimethylaminopropyl)-o-iminodibenzyl
  • N-(gamma-Dimethylaminopropyl)iminodibenzyl
  • Nelipramin
  • NSC 169866
  • Prazepine
  • Promiben
  • Pryleugan
  • Timolet
  • Tofranil
  • UNII-OGG85SX4E4

Systematic Names

  • 5H-Dibenz(b,f)azepine, 5-(3-(dimethylamino)propyl)-10,11-dihydro-
  • 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-
  • 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl- (9CI)
  • Imipramine

Registry Numbers

CAS Registry Number

  • 50-49-7

FDA UNII

  • OGG85SX4E4

Related Registry Number

  • 113-52-0 (mono-hydrochloride)

System Generated Number

  • 0000050497

Structure Descriptors

InChI

1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3

InChIKey

BCGWQEUPMDMJNV-UHFFFAOYSA-N

Smiles

N1(c2c(CCc3c1cccc3)cccc2)CCCN(C)C

Toxicity

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: COMA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980.
child LDLo oral 35mg/kg (35mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Schweizerische Medizinische Wochenschrift. Vol. 99, Pg. 1157, 1969.
child TDLo oral 30mg/kg (30mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
American Journal of Diseases of Children. Vol. 130, Pg. 507, 1976.
dog LDLo intravenous 45mg/kg (45mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

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: COMA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980.
man LDLo oral 71mg/kg (71mg/kg) ENDOCRINE: CHANGE IN LH

CARDIAC: CHANGE IN RATE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
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)   Intensive Care Medicine. Vol. 23, Pg. 480, 1997.
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) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: WAKEFULNESS

AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 245, Pg. 283, 1980.
mouse LD50 oral 188mg/kg (188mg/kg)   Pharmaceutical Chemistry Journal Vol. 14, Pg. 773, 1980.
mouse LD50 oral 188mg/kg (188mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Pharmaceutical Chemistry Journal Vol. 14, Pg. 773, 1980.
mouse LD50 subcutaneous 195ug/kg (0.195mg/kg)   Pharmaceutical Chemistry Journal Vol. 15, Pg. 412, 1981.
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) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
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) CARDIAC: OTHER CHANGES

BEHAVIORAL: COMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 51, 1995.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 174.5 deg C   EXP
pKa Dissociation Constant 9.4 (none)   EXP
log P (octanol-water) 4.8 (none)   EXP
Water Solubility 18.2 mg/L 24 EXP
Vapor Pressure 1.53E-06 mm Hg 25 EST
Henry's Law Constant 1.01E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.94E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.