CAS No.50-48-6 Amitriptyline


Name Amitriptyline
CAS Registry Number 50-48-6
Synonyms AMITRIPTYLINE;AMITRYPTYLLINE NA;3-(10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n,n-dimethyl-1-propanamine;[3-(10,11-DIHYDRO-DIBENZO[A,D]CYCLOHEPTEN-5-YLIDENE)-PROPYL]-DIMETHYL-AMINE;10,11-Dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene;10,11-dihydro-n,n-dimethyl-5h-dibenzo(a,d)heptalene-delta(sup5),gamma-propyl;10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta5,gamma-propylamine;1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-
Molecular Structure Amitriptyline   50-48-6
Molecular Formula C20H23N
Molecular Weight 277.4
mp: 196-197℃

CAS 50-48-6 Wiki / 50-48-6 MSDS

Clinical data
Pronunciation /ˌæmɪˈtrɪptɪln/[1]
Trade names Elavil, others
AHFS/ Monograph
MedlinePlus a682388
License data
  • US FDA: Amitriptyline
  • AU: C
  • US: C (Risk not ruled out)
Routes of
By mouth, intramuscular injection
ATC code
  • N06AA09 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability 30–60% due to first pass metabolism
Protein binding 96%<[2]
Metabolism Liver[2]
Biological half-life 10 to 50 hours[2]
Excretion Mostly kidney[2]
CAS Number
  • 50-48-6 YesY
    549-18-8 (hydrochloride)
    17086-03-2 (embonate)
PubChem CID
  • 2160
  • 200
  • DB00321 YesY
  • 2075 YesY
  • 1806D8D52K
  • D07448 YesY
  • CHEBI:2666 YesY
  • CHEMBL629 YesY
ECHA InfoCard 100.000.038
Chemical and physical data
Formula C20H23N
Molar mass 277.403 g/mol
3D model (JSmol)
  • Interactive image

Amitriptyline, sold under the brand name Elavil among others, is a medicine used to treat a number of mental illnesses.[2] These include major depressive disorder and anxiety disorder, and less commonly attention deficit hyperactivity disorder and bipolar disorder.[2][3] Other uses include prevention of migraines, treatment of neuropathic pain such as fibromyalgia and postherpetic neuralgia, and less commonly insomnia.[2][4] It is in the tricyclic antidepressant (TCA) class and its exact mechanism of action is unclear.[2] Amitriptyline is taken by mouth.[2]

Common side effects include a dry mouth, trouble seeing, low blood pressure on standing, sleepiness, and constipation. Serious side effects may include seizures, an increased risk of suicide in those less than 25 years of age, urinary retention, glaucoma, and a number of heart issues. It should not be taken with MAO inhibitors or the medication cisapride.[2] Amitriptyline may cause problems if taken during pregnancy.[2][5] Use during breastfeeding appears to be relatively safe.[6]

Amitriptyline was discovered in 1960[7] and approved by the US Food and Drug Administration (FDA) in 1961.[8] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[9] It is available as a generic medication.[2] The wholesale cost in the developing world as of 2014 is between 0.01 and 0.04 USD per dose.[10] In the United States it costs about 0.20 USD per dose.[2]