Desipramine hydrochlorideProduct ingredient for Desipramine
- Name
- Desipramine hydrochloride
- Drug Entry
- Desipramine
Desipramine hydrochloride is a dibenzazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, desipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, desipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as desipramine and nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline and doxepine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Desipramine exerts less anticholinergic and sedative side effects compared to tertiary amine TCAs, such as amitriptyline and clomipramine. Desipramine may be used to treat depression, neuropathic pain (unlabeled use), agitation and insomnia (unlabeled use) and attention-deficit hyperactivity disorder (unlabeled use).
- Accession Number
- DBSALT000042
- Structure
Structure for Desipramine hydrochloride (DBSALT000042)
- Synonyms
- Not Available
- UNII
- 1Y58DO4MY1
- CAS Number
- 58-28-6
- Weight
- Average: 302.842
Monoisotopic: 302.154976453 - Chemical Formula
- C18H23ClN2
- InChI Key
- XAEWZDYWZHIUCT-UHFFFAOYSA-N
- 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
- IUPAC Name
- (3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine hydrochloride
- SMILES
- Cl.CNCCCN1C2=CC=CC=C2CCC2=CC=CC=C12
- External Links
- PubChem Compound
- 65327
- ChemSpider
- 58811
- ChEBI
- 4449
- ChEMBL
- CHEMBL1696
- Wikipedia
- Desipramine
- Predicted Properties
Property Value Source Water Solubility 0.0396 mg/mL ALOGPS logP 4.02 ALOGPS logP 3.9 Chemaxon logS -3.8 ALOGPS pKa (Strongest Basic) 10.02 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 15.27 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 85.31 m3·mol-1 Chemaxon Polarizability 32.05 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon