Amitriptyline

Title: Amitriptyline
CAS Registry Number: 50-48-6
CAS Name: 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine
Additional Names: 10,11-dihydro-N,N-dimethyl-5H-dibenzo[a,d]cycloheptene-D5,g-propylamine; 5-(g-dimethylaminopropylidene)-5H-dibenzo[a,d]-10,11-dihydrocycloheptene; 10,11-dihydro-5-(g-dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene; 5-(3-dimethylaminopropylidene)dibenzo[a,d][1,4]cycloheptadiene
Molecular Formula: C20H23N
Molecular Weight: 277.40
Percent Composition: C 86.59%, H 8.36%, N 5.05%
Literature References: Prepn: Hoffsommer et al., J. Org. Chem. 27, 4134 (1962); 28, 1751 (1963); J. Med. Chem. 8, 555 (1965); Engelhardt et al., BE 584061 (1960 to Merck & Co.); GB 858187; GB 858188 (both 1961 to Hoffmann-La Roche); Tristram, Tull, US 3205264 (1965 to Merck & Co.). Toxicity data: A. Tobe et al., Arzneim.-Forsch. 31, 1278 (1981). Comprehensive description: K. W. Blessel et al., Anal. Profiles Drug Subs. 3, 127-148 (1974).
Derivative Type: Hydrochloride
CAS Registry Number: 549-18-8
Manufacturers' Codes: Ro-4-1575
Trademarks: Adepril (Teofarma); Amineurin (Hexal); Domical (Berk); Elavil (AstraZeneca); Endep (Roche); Euplit (Desitin); Laroxyl (Roche); Lentizol (Lundbeck); Miketorin (Schering); Redomex (Lundbeck); Saroten (Bayer); Sarotex (Lundbeck); Triptizol (SIT); Tryptanol (Merck & Co.); Tryptizol (Merck & Co.)
Molecular Formula: C20H23N.HCl
Molecular Weight: 313.86
Percent Composition: C 76.54%, H 7.71%, N 4.46%, Cl 11.30%
Properties: Minute crystals, mp 196-197°. Freely sol in water, chloroform, alc. uv max (methanol): 240 nm (e 13800). pKa 9.4. LD50 in mice, rats (mg/kg): 350, 380 orally; 65, 75 i.p. (Tobe).
Melting point: mp 196-197°
pKa: pKa 9.4
Absorption maximum: uv max (methanol): 240 nm (e 13800)
Toxicity data: LD50 in mice, rats (mg/kg): 350, 380 orally; 65, 75 i.p. (Tobe)
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Tricyclics.
Amitriptylinoxide Amitrole Amixetrine Amlexanox Amlodipine

Amitriptyline
Systematic (IUPAC) name
3-(10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ylidene)-N,N-dimethylpropan-1-amine
Clinical data
Trade names Amitrip, Elavil, Endep, Levate
AHFS/Drugs.com monograph
MedlinePlus a682388
Licence data US FDA:link
Pregnancy cat. C (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral, intramuscular
Pharmacokinetic data
Bioavailability 30–60% due to first pass metabolism
Protein binding 96%[1][2][3][4]
Metabolism Hepatic (CYP2D6)[1][2][3][4]
Half-life 22.4 hr (26 hr for active metabolite, nortriptyline)[1][2][3][4]
Excretion Renal[1][2][3][4]
Identifiers
CAS number 50-48-6 YesY
549-18-8 (hydrochloride)
ATC code N06AA09
PubChem CID 2160
IUPHAR ligand 200
DrugBank DB00321
ChemSpider 2075 YesY
UNII 1806D8D52K YesY
KEGG D07448 YesY
ChEBI CHEBI:2666 YesY
ChEMBL CHEMBL629 YesY
Chemical data
Formula C20H23N 
Mol. mass 277.403 g/mol
 YesY (what is this?)  (verify)

Amitriptyline (Elavil, Endep, Levate and many others) is a tricyclic antidepressant (TCA). It is the most widely used TCA and is an efficacious treatment for major depressive disorder (clinical depression). It was originally developed by Merck and was initially approved by the United States Food and Drug Administration (FDA) on 7 April 1961.[5]