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Desipramine
Desipramine
Synonyms N-desmethylimipramine
Brand names Norpramin, Pertofran
IUPAC name

IUPAC name
3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methyl-1-propanamine
ChemSpider

2888

DrugBank

DB01151

PubChem

2995

PDB fields

N/A

Formula

C18H22N2

InChI
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
InChIKey
HCYAFALTSJYZDH-UHFFFAOYSA-N
SMILES
SMILES
CNCCCN1C2=CC=CC=C2CCC3=CC=CC=C31
(Jmol 3D structure)
Mol. mass

266.3807 g/mol

Desipramine is a tricyclic antidepressant that like other TCAs is not the best tolerated of drugs, although it is better tolerated than most TCAs due to its relatively low propensity for blocking the mAChRs, α-adrenoceptors and H1 histamine receptors.[1] Despite this it is third only to amoxapine (also not available in Australia) and maprotiline (also not available in Australia) for its toxicity in overdose, when compared to other antidepressants.[2][3] It is also the active metabolite of imipramine, the first TCA to be marketed.[1]

A recent review found the evidence to date regarding its efficacy in treating cocaine addiction to be inconclusive, although a trend was observed favouring desipramine over placebo for abstinence.[4] One clinical trial (N=41) has demonstrated the possible efficacy (keeping in mind many studies go unpublished if they found negative results) of desipramine in children and adolescents with ADHD.[5]

External linksEdit

Reference listEdit

  1. 1.0 1.1 Brayfield, A, ed. (13 December 2013). "Desipramine Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 28 July 2014.
  2. Hawton, K; Bergen, H; Simkin, S; Cooper, J; Waters, K; Gunnell, D; Kapur, N (May 2010). "Toxicity of antidepressants: rates of suicide relative to prescribing and non-fatal overdose.". The British Journal of Psychiatry 196 (5): 354–8. PMC 2862059. PMID 20435959. doi:10.1192/bjp.bp.109.070219. 
  3. White, N; Litovitz, T; Clancy, C (December 2008). "Suicidal antidepressant overdoses: a comparative analysis by antidepressant type.". Journal of Medical Toxicology 4 (4): 238–50. PMC 3550116. PMID 19031375. doi:10.1007/BF03161207. 
  4. Pani, PP; Trogu, E; Vecchi, S; Amato, L (December 2011). "Antidepressants for cocaine dependence and problematic cocaine use.". The Cochrane Database of Systematic Reviews (12): CD002950. PMID 22161371. doi:10.1002/14651858.CD002950.pub3. 
  5. Spencer, T; Biederman, J; Coffey, B; Geller, D; Crawford, M; Bearman, SK; Tarazi, R; Faraone, SV (July 2002). "A double-blind comparison of desipramine and placebo in children and adolescents with chronic tic disorder and comorbid attention-deficit/hyperactivity disorder.". Archives of General Psychiatry 59 (7): 649–56. doi:10.1001/archpsyc.59.7.649. PMID 12090818.

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