Desipramine

Title: Desipramine
CAS Registry Number: 50-47-5
CAS Name: 10,11-Dihydro-N-methyl-5H-dibenz[b,f]azepine-5-propanamine
Additional Names: 10,11-dihydro-5-[3-(methylamino)propyl]-5H-dibenz[b,f]azepine; 5-(g-methylaminopropyl)iminodibenzyl; N-(3-methylaminopropyl)iminobibenzyl; desmethylimipramine; norimipramine
Molecular Formula: C18H22N2
Molecular Weight: 266.38
Percent Composition: C 81.16%, H 8.32%, N 10.52%
Literature References: Prepn: GB 908788; BE 614616 (both 1962 to Geigy); J. H. Biel, C. I. Judd, GB 980231 (1965 to Lakeside); eidem, US 3454554 (1969 to Colgate Palmolive). Chemistry, pharmacology: E. Eriksoo, O. Rohte, Arzneim.-Forsch. 20, 1561 (1970). Clinical response, plasma levels, pharmacokinetics: P. D. Hrdina, Y. D. Lapierre, Prog. Neuro-Psychopharmacol. 4, 591 (1980). Mechanism of action study: S. A. Checkley et al., Br. J. Psychiatry 138, 248 (1981). Efficacy in depression: W. Z. Potter et al., Psychopharmacol. Bull. 17, 26 (1981); J. W. Stewart et al., ibid. 136. Teratological study: L. Aeppli, Arzneim.-Forsch. 19, 1617 (1969). Carcinogenicity and mutagenicity study: H. Kubinski et al., Mutat. Res. 89, 95 (1981). Has been found to be one of the most effective cmpds described for in vitro and in vivo reversal of chloroquine, q.v., resistance in Plasmodium falciparum: A. J. Bitonti et al., Science 242, 1301 (1988).
Properties: bp0.02 172-174°. uv max: 213, 252 nm (log e 4.39, 3.93).
Boiling point: bp0.02 172-174°
Absorption maximum: uv max: 213, 252 nm (log e 4.39, 3.93)
Derivative Type: Hydrochloride
CAS Registry Number: 58-28-6
Manufacturers' Codes: G-35020; JB-8181; NSC-114901
Trademarks: Norpramin (Aventis); Nortimil (Chiesi); Pertofran (Novartis); Pertofrane (Novartis); Petylyl (Temmler)
Molecular Formula: C18H22N2.HCl
Molecular Weight: 302.84
Percent Composition: C 71.39%, H 7.66%, N 9.25%, Cl 11.71%
Properties: Crystals from methanol ether, mp 215-216°. Sol in water. LD50 in mice, rats (mg/kg): 500, 385 orally; 94, 48 i.p.; 420, 183 s.c. (Eriksoo, Rohte).
Melting point: mp 215-216°
Toxicity data: LD50 in mice, rats (mg/kg): 500, 385 orally; 94, 48 i.p.; 420, 183 s.c. (Eriksoo, Rohte)
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Tricyclics.
Deslanoside Desloratadine Deslorelin Desmopressin Desmosterol

Desipramine
Desipramine.svg
Systematic (IUPAC) name
3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine
Clinical data
Trade names Norpramin
AHFS/Drugs.com monograph
MedlinePlus a682387
Pregnancy cat. C (US)
Legal status -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 73-92%
Metabolism Hepatic (CYP2D6)
Half-life 15-24 hours
Excretion Urine (70%)
Identifiers
CAS number 50-47-5 YesY
ATC code N06AA01
PubChem CID 2995
IUPHAR ligand 2399
DrugBank DB01151
ChemSpider 2888 YesY
UNII TG537D343B YesY
KEGG D07791 YesY
ChEBI CHEBI:47781 YesY
ChEMBL CHEMBL72 YesY
Chemical data
Formula C18H22N2 
Mol. mass 266.381 g/mol
 YesY (what is this?)  (verify)

Desipramine (also known as desmethylimipramine) is a tricyclic antidepressant (TCA). It inhibits the reuptake of norepinephrine and to a minor extent serotonin. It is used to treat depression, but not considered a first line treatment since the introduction of SSRI antidepressants. Desipramine is an active metabolite of imipramine. It is sold under the brand names Norpramin and Pertofrane.

Along with other tricyclics, desipramine has found use in treating neuropathic pain. The mechanism of action seems to involve the activation, through norepinephrine reuptake inhibition, of descending pathways in the spinal cord that block pain signals from ascending to the brain. Desipramine is one of the most potent and selective medications in this respect. It may also be used to treat symptoms of Attention Deficit Hyperactivity Disorder, as the underproduction of norepinephrine has been increasingly linked to symptoms associated with Attention Deficit Disorder[citation needed]. It may also be used to treat symptoms of cocaine withdrawal.[citation needed]