Compound: amitriptyline
SMILES: N(CCC=C1c2c(cccc2)CCc3c1cccc3)(C)C
InChIKey: KRMDCWKBEZIMAB-UHFFFAOYSA-N
Synonyms: amitriptyline, 50-48-6, Amitriptylin, Seroten, Damitriptyline, Triptanol, Flavyl, Proheptadiene, Damilen, Triptisol, Adepril, Elavil, Lantron, Amitryptiline, Tryptanol, Adepress, Redomex, Triptilin, Laroxyl, Amitriptilina, Amytriptylin, Amitriptylinum, Amitryptyline, Ro 4-1575, 5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene, 3-(10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine, 10,11-Dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene, N 750, 5-(3'-Dimethylaminopropylidene)-dibenzo-(a,d)(1,4)-cycloheptadiene, 3-(10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-5-yliden)-N,N-dimethylpropylamin, 5H-Dibenzo(a,d)cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-N,N-dimethyl-, 1806D8D52K, 5-(gamma-Dimethylaminopropylidine)-5H-dibenzo(a,d)(1,4)cycloheptadiene, 5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptatriene, 5-(gamma-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene, 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-, 10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta(sup 5),gamma-propylamine, CHEBI:2666, DTXSID7022594, 5-(gamma-Dimethylaminopropylidene)-5H-Dibenzo[a,d][1,4]cycloheptadiene, 10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta(5),gamma-propylamine, 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-, 5-(gamma-Dimethylaminopropylidene)-5H-dibenzo(a,d)(1,4)cycloheptadiene, 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethylpropan-1-amine, 5H-Dibenzo(a,d)cycloheptene-delta(sup 5),gamma-propylamine, 10,11-dihydro-N,N-dimethyl-, 5-(3'-Dimethylaminopropylidene)-dibenzo-[a,d][1,4]-cycloheptadiene, 10,11-dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene, dimethyl({3-[(2Z)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine, Apo Amitriptyline, 3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethylpropan-1-amine, RPh, Amitriptylin, dimethyl((3-((2E)-tricyclo(9.4.0.0^(3,8))pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene)propyl))amine, dimethyl((3-((2Z)-tricyclo(9.4.0.0^(3,8))pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene)propyl))amine, dimethyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene]propyl})amine, Desitin, Amitriptylin, Amitriptylin neuraxpharm, RefChem:5544, DTXCID502594, N06AA09, 200-041-6, dimethyl(3-(tricyclo(9.4.0.03,8)pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene)propyl)amine, Tryptizol, Amitriprolidine, Damilan, Sarotex, MK 230, 3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine, Amitriptyline (INN), HSDB 3007, CHEMBL629, N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine, Amytriptiline, Laroxil, Elanil, Amitriptylin [German], Amitriptilina [Italian], AMITRIPTYLINE [INN], Amitriptyline [INN:BAN], Amitriptylinum [INN-Latin], Amitriptilina [INN-Spanish], 3-(1011-Dihydro-5H-dibenzo[ad][7]annulen-5-ylidene)-NN-dimethylpropan-1-amine, 5H-Dibenzo[a,d]cycloheptene-.delta.5,.gamma.-propylamine, 10,11-dihydro-N,N-dimethyl-, TP0, Laroxyl (TN), CCRIS 9174, NCGC00015095-09, CAS-549-18-8, EINECS 200-041-6, BRN 2217885, UNII-1806D8D52K, Domical (Salt/Mix), Laroxyl (Salt/Mix), Lentizol (Salt/Mix), Vanatrip (Salt/Mix), Triptizol (Salt/Mix), Spectrum_000044, Prestwick0_000074, Prestwick1_000074, Prestwick2_000074, Prestwick3_000074, Spectrum2_000101, Spectrum3_000298, Spectrum4_000146, Spectrum5_000806, Lopac-A-8404, AMITRIPTYLINE [MI], EC 200-041-6, SCHEMBL7824, Lopac0_000112, Oprea1_479304, AMITRIPTYLINE [VANDF], BSPBio_000287, BSPBio_001836, GTPL200, KBioGR_000592, KBioGR_002261, KBioSS_000424, KBioSS_002262, AMITRIPTYLINE [MART.], BIDD:GT0115, DivK1c_000766, SPBio_000082, SPBio_002208, AMITRIPTYLINE [WHO-DD], BPBio1_000317, orb1306054, SCHEMBL29359365, KBio1_000766, KBio2_000424, KBio2_002261, KBio2_002992, KBio2_004829, KBio2_005560, KBio2_007397, KBio3_001336, KBio3_002741, cMAP_000001, NINDS_000766, HMS5087O07, 5-(3-dimethylaminopropylidene)dibenzo[a,d][1,4]-cycloheptadiene, HY-B0527, MSK10058, PS01 - Amitriptyline/Nortriptyline, AMITRIPTYLINE [USP IMPURITY], Amitriptyline EP Impurity C-D3 Hcl, BDBM50020712, MFCD00412072, PDSP1_001564, PDSP2_001548, s5947, SBB080793, STK525215, 5-(3-Dimethylaminopropylidene)-5H-dibenzo[a,d]-10,11-dihydrocycloheptene, 5-(gamma-Dimethylaminopropylidene)-5H-dibenzo[a,d]10,11-dihydrocycloheptene, AKOS000512694, CCG-204207, DB00321, SDCCGSBI-0050100.P005, IDI1_000766, MRF-0000533, NCGC00015095-01, NCGC00015095-02, NCGC00015095-03, NCGC00015095-04, NCGC00015095-05, NCGC00015095-06, NCGC00015095-07, NCGC00015095-08, NCGC00015095-10, NCGC00015095-11, NCGC00015095-12, NCGC00015095-14, NCGC00015095-26, NCGC00024433-04, NCGC00183047-01, DA-50424, SBI-0050100.P004, 3B - Known Drug Blood Quantification Sample, AB00514631, AmitriptylineMK-230, N-750, Ro41575, CS-0009498, NS00000032, C06824, D07448, Q58397, AB00053417-12, AB00053417_13, AB00053417_14, L001041, BRD-K53737926-003-05-4, BRD-K53737926-003-14-6, BRD-K53737926-003-25-2, BRD-K53737926-003-27-8, Nortriptyline Hydrochloride EP Impurity F; Amitriptyline, NORTRIPTYLINE HYDROCHLORIDE IMPURITY F [EP IMPURITY], (3-(5,6-dihydrodibenzo[b,f][7]annulen-11-ylidene)propyl)dimethylamine, 5-(.gamma.-Dimethylaminopropylidene)-5H-Dibenzo[a,d][1,4]cycloheptadiene, 5-(.gamma.-Dimethylaminopropylidine)-5H-dibenzo(a,d)(1,4)cycloheptadiene, 10,11-Dihydro-5-(.gamma.-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene, 10,11-dihydro-N,N-dimethl-5H-dibenzo[a,d]cycloheptene-(delta(5, gamma))-propylamine, 10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-.DELTA.5,.gamma.-propylamine, 10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta5,gamma-propylamine, 3-(5,6-dihydrodibenzo[[?],[?]][7]annulen-11-ylidene)-N,N-dimethyl-propan-1-amine, 5-(.gamma.-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene, 5-(.gamma.-Dimethylaminopropylidene)-5H-dibenzo(a,d)-10,11-dihydrocycloheptene, N-[3-(10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5-YLIDEN)PROPYL]-N,N-DIMETHYLAMINE, 3-(10 pound not11-Dihydro-5H-dibenzo[a pound notd][7]annulen-5-ylidene)-N pound notN-dimethylpropan-1-amine, 3-(10,11-Dihydro-5H-dibenzo-[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine, hydrochloride, 5H-Dibenzo(a,d)cycloheptene-.delta.(sup 5),.gamma.-propylamine, 10,11-dihydro-N,N-dimethyl-, 5H-Dibenzo[a,d]cycloheptene-Delta5,gamma-propylamine, 10,11-dihydro-N,N-dimethyl- (6CI,8CI) 5-(gamma-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene
Theoretical properties:
molecular_formula: C20H23N
molecular_weight: 277.4 g/mol
exact_mass: 277.183049738 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 3
heavy_atom_count: 21
topological_polar_surface_area: 3.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
boiling_point: 410.26°C (rough estimate)
melting_point: 196-197
solubility: freely soluble in water
Descriptions:
pubchem: Amitriptyline is an organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5. It has a role as a tropomyosin-related kinase B receptor agonist, an antidepressant, an adrenergic uptake inhibitor, a xenobiotic and an environmental contaminant. It is a tertiary amine and a carbotricyclic compound. It derives from a hydride of a dibenzo[a,d][7]annulene.
chebi: An organic tricyclic compound that is 10,11-dihydro-5<em>H</em>-dibenzo[<em>a,d</em>][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.
chembl: AMITRIPTYLINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Amitriptyline, formerly sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat major depressive disorder, and a variety of pain syndromes such as neuropathic pain, fibromyalgia, migraine and tension headaches. Due to the frequency and prominence of side effects, amitriptyline is generally considered a second-line therapy for these indications.
The most common side effects are dry mouth, drowsiness, dizziness, constipation, and weight gain. Glaucoma, liver toxicity and abnormal heart rhythms are rare but serious side effects. Blood levels of amitriptyline vary significantly from one person to another, and amitriptyline interacts with many other medications potentially aggravating its side effects.
Amitriptyline was discovered in the late 1950s by scientists at Merck and approved by the US Food and Drug Administration (FDA) in 1961. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2023, it was the 90th most commonly prescribed medication in the United States, with more than 7 million prescriptions.