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Substance Name: Desipramine hydrochloride [USAN:USP:JAN]
RN: 58-28-6
UNII: 1Y58DO4MY1
InChIKey: XAEWZDYWZHIUCT-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.Cl-H

Molecular Weight

  • 302.8467
 

Classification Codes

  • Antidepressant
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Desipramine hydrochloride [USAN:USP:JAN]

Synonyms

  • 10,11-Dihydro-5-(3-(methylamino)propyl)-5H-dibenz(b,f)azepine hydrochloride
  • 10,11-Dihydro-5-(3-(methylamino)propyl)-5H-dibenz(b,f)azepine monohydrochloride
  • 5H-Dibenz(b,f)azepine, 10,11-dihydro-5-(3-(methylamino)propyl)-, hydrochloride
  • 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N-methyl-, monohydrochloride
  • Demethylimipramine hydrochloride
  • Desimipramine, hydrochloride
  • Desipramine HCl
  • Desipramine hydrochloride
  • Desipramine monohydrochloride
  • Desmethylimipramine chloride
  • Desmethylimipramine hydrochloride
  • Desmethylimipramine monohydrochloride
  • DMI
  • DMI hydrochloride
  • EINECS 200-373-1
  • EX 4355
  • G 35020
  • G-35020
  • GMI
  • Imipraminedemethyl hydrochloride
  • JB 8181
  • JB-8181
  • N-(gamma-Methylaminopropyl)iminodibenzyl hydrochloride
  • Norpolake
  • Norpramin
  • Nortimil
  • NSC 114901
  • NSC-114901
  • Pertofran
  • Pertofrane
  • Pertofrin
  • Petylyl
  • RMI 9,384A
  • UNII-1Y58DO4MY1

Systematic Names

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

Registry Numbers

CAS Registry Number

  • 58-28-6

FDA UNII

  • 1Y58DO4MY1

Related Registry Number

  • 50-47-5 (Parent)

System Generated Number

  • 0000058286

Molecular Formulas

Molecular Formula

  • C18-H22-N2.Cl-H

Molecular Formula Fragments

  • C18-H22-N2
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C18H22N2.ClH/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;1H

InChIKey

XAEWZDYWZHIUCT-UHFFFAOYSA-N

Smiles

Cl.CNCCCN1c2ccccc2CCc3ccccc13

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 25mg/kg (25mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
guinea pig LDLo intravenous 55mg/kg (55mg/kg) CARDIAC: OTHER CHANGES Therapie. Vol. 20, Pg. 67, 1965.
man TDLo oral 490ug/kg (0.49mg/kg) BEHAVIORAL: SLEEP Journal of Clinical Psychiatry. Vol. 47, Pg. 210, 1986.
man TDLo oral 5mg/kg/5D-I (5mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS
American Journal of Psychiatry. Vol. 142, Pg. 386, 1985.
mouse LD50 intraperitoneal 88mg/kg (88mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
mouse LD50 intravenous 37mg/kg (37mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
International Journal of Neuropharmacology. Vol. 4, Pg. 111, 1965.
mouse LD50 oral 315mg/kg (315mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
rat LD50 intraperitoneal 55mg/kg (55mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
rat LD50 intravenous 19mg/kg (19mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
rat LD50 oral 871mg/kg (871mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 1411, 1983.
women TDLo oral 14mg/kg/1W-I (14mg/kg)   Journal of Clinical Psychiatry. Vol. 44, Pg. 153, 1983.
women TDLo oral 14mg/kg/1W-I (14mg/kg)   Journal of Clinical Psychiatry. Vol. 44, Pg. 153, 1983.
women TDLo oral 14mg/kg/1W-I (14mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED Journal of Clinical Psychiatry. Vol. 44, Pg. 153, 1983.
women TDLo oral 36mg/kg/6D-I (36mg/kg) GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Clinical Psychiatry. Vol. 53, Pg. 160, 1992.
women TDLo oral 45mg/kg (45mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Annals of Pharmacotherpy. Vol. 27, Pg. 572, 1993.
women TDLo oral 70mg/kg/4W-I (70mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS
American Journal of Psychiatry. Vol. 142, Pg. 386, 1985.