Imipramine hydrochlorideProduct ingredient for Imipramine
- Name
- Imipramine hydrochloride
- Drug Entry
- Imipramine
Imipramine, the prototypical tricyclic antidepressant (TCA), is a dibenzazepine-derivative 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, imipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, imipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as imipramine and amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. 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 5. Imipramine has less sedative and anticholinergic effects than the tertiary amine TCAs, amitriptyline and clomipramine. Imipramine may be used to treat depression and nocturnal enuresis in children Label. Unlabeled indications include chronic and neuropathic pain (including diabetic neuropathy), panic disorder, attention-deficit/hyperactivity disorder (ADHD), and post-traumatic stress disorder (PTSD) 12,11,1,13,14,15,2.
- Accession Number
- DBSALT000099
- Structure
- Synonyms
- Imipramine HCl
- UNII
- BKE5Q1J60U
- CAS Number
- 113-52-0
- Weight
- Average: 316.868
Monoisotopic: 316.170626517 - Chemical Formula
- C19H25ClN2
- InChI Key
- XZZXIYZZBJDEEP-UHFFFAOYSA-N
- InChI
- InChI=1S/C19H24N2.ClH/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21;/h3-6,8-11H,7,12-15H2,1-2H3;1H
- IUPAC Name
- (3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine hydrochloride
- SMILES
- Cl.CN(C)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12
- External Links
- KEGG Compound
- C07982
- PubChem Compound
- 8228
- ChemSpider
- 7935
- ChEBI
- 5882
- ChEMBL
- CHEMBL1692
- Wikipedia
- Imipramine
- Predicted Properties
Property Value Source Water Solubility 0.0664 mg/mL ALOGPS logP 4.53 ALOGPS logP 4.28 Chemaxon logS -3.6 ALOGPS pKa (Strongest Basic) 9.2 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 6.48 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 90.61 m3·mol-1 Chemaxon Polarizability 33.9 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