Compound: imipramine
SMILES: N1(c2c(cccc2)CCc3c1cccc3)CCCN(C)C
InChIKey: BCGWQEUPMDMJNV-UHFFFAOYSA-N
Synonyms: imipramine, 50-49-7, Melipramine, Antideprin, Berkomine, Imidobenzyle, Dimipressin, Melipramin, Dynaprin, Intalpram, Nelipramin, Timolet, Irmin, Dpid, Dyna-zina, Impramine, Censtim, Censtin, Imiprin, Promiben, Iramil, Imipramina, Imipraminum, Psychoforin, Eupramin, Imavate, Surplix, Imipramin, Imizinum, Imizine, N-(gamma-Dimethylaminopropyl)iminodibenzyl, Cristalia, Sermonil, N-(3-Dimethylaminopropyl)-o-iminodibenzyl, 2,2'-(3-Dimethylaminopropylimino)bibenzyl, 2,2'-(3-Dimethylaminopropylimino)dibenzyl, 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine, 1-(3-Dimethylaminopropyl)-4,5-dihydro-2,3,6,7-dibenzazepine, ORG-2463, 5-(3-(Dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine, OGG85SX4E4, Chimoreptin, Feinalmin, Imilanyle, Teperine, NSC-169866, 5,6-Dihydro-N-(3-(dimethylamino)propyl)-11H-dibenz(b,e)azepine, 5-(3-Dimethylaminopropyl)-10,11-dihydro-5H-dibenzo(b,f)azepine, DTXSID1043881, 10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine, 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-, 5H-Dibenz(b,f)azepine, 10,11-dihydro-5-(3-(dimethylamino)propyl)-, DTXCID9023881, CHEBI:47499, 5H-Dibenz(b,f)azepine, 5-(3-(dimethylamino)propyl)-10,11-dihydro-, NSC169866, 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine, 5H-Dibenz[b,f]azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-, 10,11-dihydro-N,N-dimethyl-5H-dibenz(b,f)azepine-5-propanamine, 3-(5,6-dihydrobenzo(b)(1)benzazepin-11-yl)-N,N-dimethylpropan-1-amine, 5H-Dibenz[b,f]azepine, 5-[3-(dimethylamino)propyl]-10,11-dihydro-, (3-(2-azatricyclo(9.4.0.0^(3,8))pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl)propyl)dimethylamine, (3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylamine, RefChem:5903, imizinum (for the hydrochloride), N06AA02, (3-(2-azatricyclo(9.4.0.03,8)pentadeca-1(15),3,5,7,11,13-hexaen-2-yl)propyl)dimethylamine, 200-042-1, 3-(5H-DIBENZO(b,F)azepin-5-yl)-N,N-dimethylpropan-1-amine, Norchlorimipramine, Declomipramine, 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine, Tofranil, base, Imizin, Tofranil (free base), SK-Pramine, Imipramine (INN), NSC 169866, CHEMBL11, N-(.gamma.-Dimethylaminopropyl)iminodibenzyl, 5,e)azepine, 5,e]azepine, Imidol, NCGC00015563-07, Imipramina [Italian], IMIPRAMINE [INN], Tofranil (TN), 10,11-Dihydro-5-(3-(dimethylamino)propyl)-5H-dibenz[b,f]azepine, Imipramine [INN:BAN], IMIPRAMINE-D3 HYDROCHLORIDE 98 ATOM % D, Imipraminum [INN-Latin], Imipramina [INN-Spanish], 3-(10,11-dihydro-5h-dibenz[b,f]azepin-5-yl)propyldimethylamine, CAS-50-49-7, 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine;3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine, CCRIS 9173, 2241983-10-6, HSDB 3100, 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethyl-propan-1-amine, Janimine (hydrochloride), Tofranil (hydrochloride), CAS-113-52-0, EINECS 200-042-1, UNII-OGG85SX4E4, BRN 0256892, 5H-Dibenz(b, 5-(3-(dimethylamino)propyl)-10,11-dihydro-, 5H-Dibenz[b, 5-[3-(dimethylamino)propyl]-10,11-dihydro-, Tofranil base, (3-{2-azatricyclo[9.4.0.0,3,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylamine, IXX, Imizin (Salt/Mix), Imavate (Salt/Mix), Imizine (Salt/Mix), Surplix (Salt/Mix), Eupramin (Salt/Mix), Imizinum (Salt/Mix), Tofranil (Salt/Mix), Spectrum_000915, IMIPRAMINE [MI], Psychoforin (Salt/Mix), Prestwick0_000072, Prestwick1_000072, Prestwick2_000072, Prestwick3_000072, SK-Pramine (Salt/Mix), Spectrum2_000990, Spectrum3_000466, Spectrum4_000016, Spectrum5_000864, Clomipramine Impurity 10, IMIPRAMINE [HSDB], Lopac-I-7379, IMIPRAMINE [VANDF], IMIPRAMINE [MART.], IMIPRAMINE [WHO-DD], Lopac0_000702, Oprea1_200908, SCHEMBL34282, BSPBio_000283, BSPBio_002172, GTPL357, KBioGR_000391, KBioSS_001395, BIDD:GT0116, DivK1c_000559, SPBio_001059, SPBio_002204, G-22355 (Salt/Mix), BPBio1_000313, orb1705856, SCHEMBL29350100, HY-B1490A, KBio1_000559, KBio2_001395, KBio2_003963, KBio2_006531, KBio3_001392, NINDS_000559, HMS2089G08, Tox21_110174, BDBM50010859, CCG-36485, EBC-26430, MFCD00242921, STL416211, AKOS016010320, Tox21_110174_1, DB00458, SDCCGSBI-0050680.P005, IDI1_000559, MRF-0000592, NCGC00015563-01, NCGC00015563-02, NCGC00015563-03, NCGC00015563-04, NCGC00015563-05, NCGC00015563-06, NCGC00015563-08, NCGC00015563-09, NCGC00015563-10, NCGC00015563-11, NCGC00015563-13, NCGC00015563-25, NCGC00024253-03, NCGC00024253-04, 5-(3-Dimethylaminopropyl)-10,f)azepine, DA-69850, FI176386, SY284544, Trimipramine maleate impurity, imipramine-, SBI-0050680.P004, WLN: T C676 BN&T&J B3N1&1, 5-(3-(Dimethylamino)propyl)-10,f)azepine, AB00053486, CS-0013621, NS00008106, 5H-Dibenz[b, 10,11-dihydro-N,N-dimethyl-, C07049, D08070, EN300-708790, G82405, Q58396, AB00053486-15, AB00053486_16, AB00053486_17, 1-(3-Dimethylaminopropyl)-4,3,6,7-dibenzazepine, F600887, L000739, BRD-K38436528-003-05-5, BRD-K38436528-003-15-4, BRD-K38436528-003-25-3, BRD-K38436528-003-26-1, BRD-K38436528-003-27-9, TRIMIPRAMINE MALEATE IMPURITY D [EP IMPURITY], 5H-Dibenz(b, 10,11-dihydro-5-(3-(dimethylamino)propyl)-, CLOMIPRAMINE HYDROCHLORIDE IMPURITY B [EP IMPURITY], 5H-Dibenz[b,f]azepine, 5-(dimethylamino)propyl-10,11-dihydro-, TRIMIPRAMINE MALEATE IMPURITY, IMIPRAMINE- [USP IMPURITY], 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine, Imipramine; Clomipramine EP Impurity B; Trimipramine Maleate EP Impurity D, 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine #, InChI=1/C19H24N2/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,7,12-15H2,1-2H
Theoretical properties:
molecular_formula: C19H24N2
molecular_weight: 280.4 g/mol
exact_mass: 280.193948774 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 4
heavy_atom_count: 21
topological_polar_surface_area: 6.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off-white /hydrochloride/
color: White to off-white /hydrochloride/
odor: Odorless /hydrochloride/
melting_point: 174-175
Descriptions:
pubchem: Imipramine is a dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom. It has a role as an antidepressant, an adrenergic uptake inhibitor and an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor. It derives from a hydride of a 5H-dibenzo[b,f]azepine.
chebi: A dibenzoazepine that is 5<em>H</em>-dibenzo[<em>b</em>,<em>f</em>]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.
chembl: IMIPRAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Imipramine, sold under the brand name Tofranil, among others, is a tricyclic antidepressant (TCA) mainly used in the treatment of depression. It is also effective in treating anxiety and panic disorder. Imipramine is taken by mouth.
Common side effects of imipramine include dry mouth, drowsiness, dizziness, low blood pressure, rapid heart rate, urinary retention, and electrocardiogram changes. Overdose of the medication can result in death. Imipramine appears to work by increasing levels of serotonin and norepinephrine and by blocking certain serotonin, adrenergic, histamine, and cholinergic receptors.
Imipramine was discovered in 1951 and was introduced for medical use in 1957. It was the first TCA to be marketed. Imipramine and TCAs other than amitriptyline (which, at least in the U.K., is prescribed comparatively as frequently as SSRIs) have decreased in prescription frequency with the rise of SSRIs—which have fewer inherent side effects and are far safer in overdose. Regardless of its caveats, imipramine retains importance in psychopharmacology and pediatrics (e.g., with childhood enuresis).