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Substance Name: Desipramine [INN:BAN]
RN: 50-47-5
UNII: TG537D343B
InChIKey: HCYAFALTSJYZDH-UHFFFAOYSA-N

Note

  • A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.

Molecular Formula

  • C18-H22-N2

Molecular Weight

  • 266.386
 

Classification Codes

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

Names and Synonyms

Name of Substance

  • Desipramine
  • Desipramine [INN:BAN]

MeSH Heading

  • Desipramine

Synonyms

  • 10,11-Dihydro-5-(3-methylaminopropyl)-5H-dibenz(b,f)azepine
  • 5-(gamma-Methylaminopropyl)iminodibenzyl
  • 5-20-08-00096 (Beilstein Handbook Reference)
  • 5H-Dibenz(b,f)azepine, 10,11-dihydro-5-(3-(methylamino)propyl)-
  • 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N-methyl-
  • BRN 1432747
  • CCRIS 7091
  • Demethylimipramine
  • Desimipramine
  • Desipramin
  • Desipramina
  • Desipramina [INN-Spanish]
  • Desipramine
  • Desipramine (D4)
  • Desipraminum
  • Desipraminum [INN-Latin]
  • Desmethylimipramine
  • Dezipramine
  • Dimethylimipramine
  • DMI
  • DMI (pharmaceutical)
  • DMI 50475
  • EINECS 200-040-0
  • HSDB 3052
  • Imipramine, demethyl-
  • Methylaminopropyliminodibenzyl
  • Monodemethylimipramine
  • N-(3-Methylaminopropyl)iminobibenzyl
  • Norimipramine
  • Pertofrane
  • UNII-TG537D343B

Systematic Names

  • 5H-Dibenz(b,f)azepine, 10,11-dihydro-5-(3-(methylamino)propyl)-
  • 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N-methyl-
  • Desipramine

Registry Numbers

CAS Registry Number

  • 50-47-5

FDA UNII

  • TG537D343B

Related Registry Number

  • 58-28-6 (hydrochloride)

System Generated Number

  • 0000050475

Structure Descriptors

InChI

1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3

InChIKey

HCYAFALTSJYZDH-UHFFFAOYSA-N

Smiles

N1(c2c(CCc3c1cccc3)cccc2)CCCNC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 125mg/kg (125mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Psychopharmacologia Vol. 10, Pg. 431, 1967.
human LDLo oral 30mg/kg (30mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: COMA

BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES
Deutsche Medizinische Wochenschrift. Vol. 93, Pg. 117, 1968.
man TDLo oral 1643mg/kg/1Y- (1643mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Clinical Pediatrics Vol. 31, Pg. 635, 1992.
mouse LD50 intraperitoneal 85mg/kg (85mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 1727, 1971.
mouse LD50 intravenous 22mg/kg (22mg/kg)   Acta Pharmaceutica Suecica. Vol. 12, Pg. 173, 1975.
mouse LD50 oral 448mg/kg (448mg/kg)   Japanese Journal of Pharmacology. Vol. 21, Pg. 47, 1971.
mouse LD50 subcutaneous 214mg/kg (214mg/kg)   Farmaco, Edizione Pratica. Vol. 25, Pg. 519, 1970.
rabbit LD50 intravenous 12mg/kg (12mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964.
rabbit LD50 oral 1gm/kg (1000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1617, 1969.
rat LD50 intraperitoneal 48mg/kg (48mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1561, 1970.
rat LD50 intravenous 29mg/kg (29mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 560, 1964.
rat LD50 oral 375mg/kg (375mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1617, 1969.
rat LD50 subcutaneous 183mg/kg (183mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1561, 1970.
women LDLo oral 30mg/kg (30mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 201, 1969.
women TDLo oral 59mg/kg (59mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Mayo Clinic Proceedings. Vol. 59, Pg. 574, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 10.4 (none)   EXP
log P (octanol-water) 4.9 (none)   EXP
Water Solubility 58.6 mg/L 24 EXP
Vapor Pressure 1.56E-06 mm Hg 25 EST
Henry's Law Constant 4.60E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.89E-10 cm3/molecule-sec 25 EST

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