Record Information
Version1.0
Creation Date2016-05-22 04:16:59 UTC
Update Date2026-04-05 17:57:51 UTC
Accession NumberCHEM017375
Identification
Common NameAmitriptyline hydrochloride
ClassSmall Molecule
Description
Amitriptyline, sold under the brand name Elavil among others, is a medicine primarily used to treat a number of mental illnesses. These include major depressive disorder and anxiety disorders, and less commonly attention deficit hyperactivity disorder, bipolar disorder. Other uses include prevention of migraines, treatment of neuropathic pain such as fibromyalgia and postherpetic neuralgia, and less commonly insomnia. It is in the tricyclic antidepressant (TCA) class and its exact mechanism of action is unclear. Amitriptyline is taken by mouth.Common side effects include blurred vision, dry mouth, 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. Amitriptyline may cause problems if taken during pregnancy. Use during breastfeeding appears to be relatively safe.Amitriptyline was discovered in 1960 and approved by the US Food and Drug Administration (FDA) in 1961. It is on the World Health Organization's List of Essential Medicines, which lists the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world as of 2014 was between 0.01 and US$0.04 per dose. In the United States, it costs about US$0.20 per dose. In 2016, it was the 88th most prescribed medication in the United States, with more than 8 million prescriptions.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
ElavilKegg
Amitriptylin desitinMeSH
Amitriptylin RPHMeSH
AnapsiqueMeSH
SarotexMeSH
EndepMeSH
DamilenMeSH
TryptizolMeSH
AmitriptylineMeSH
AmitrolMeSH
NovoprotectMeSH
Desitin, amitriptylinMeSH
Amitriptylin betaMeSH
LaroxylMeSH
AmineurinMeSH
Apo-amitriptylineMeSH
TryptanolMeSH
SyneudonMeSH
TryptineMeSH
AmitripMeSH
RPH, AmitriptylinMeSH
LentizolMeSH
Amitriptylin neuraxpharmMeSH
TriptafenMeSH
DomicalMeSH
SarotenMeSH
Amitriptylin-neuraxpharmMeSH
Apo amitriptylineMeSH
Amrad brand OF amitriptyline hydrochlorideMeSH
ApoAmitriptylineMeSH
Betapharm brand OF amitriptyline hydrochlorideMeSH
Cahill may roberts brand OF amitriptyline hydrochlorideMeSH
DDSA brand OF amitriptyline hydrochlorideMeSH
Merck sharp and dohme brand OF amitriptyline hydrochlorideMeSH
neuro Hexal brand OF amitriptyline hydrochlorideMeSH
Rhône poulenc rorer brand OF amitriptyline hydrochlorideMeSH
Zeneca brand OF amitriptyline hydrochlorideMeSH
Neuraxpharm brand OF amitriptyline hydrochlorideMeSH
Apotex brand OF amitriptyline hydrochlorideMeSH
Cahill may roberts brand OF amitriptyline embonateMeSH
Desitin brand OF amitriptyline hydrochlorideMeSH
Krewel brand OF amitriptyline hydrochlorideMeSH
Merck brand OF amitriptyline hydrochlorideMeSH
Merck sharp and dohme brand OF amitriptyline embonateMeSH
Rhône-poulenc rorer brand OF amitriptyline hydrochlorideMeSH
Rodleben brand OF amitriptyline hydrochlorideMeSH
Lundbeck brand OF amitriptyline hydrochlorideMeSH
Parke davis brand OF amitriptyline hydrochlorideMeSH
beta, AmitriptylinMeSH
APS brand OF amitriptyline hydrochlorideMeSH
Alphapharm brand OF amitriptyline hydrochlorideMeSH
AmitriptylinneuraxpharmMeSH
Bayer brand OF amitriptyline hydrochlorideMeSH
Douglas brand OF amitriptyline hydrochlorideMeSH
Goldshield brand OF amitriptyline hydrochlorideMeSH
Hexal brand OF amitriptyline hydrochlorideMeSH
Protea brand OF amitriptyline hydrochlorideMeSH
Psicofarma brand OF amitriptyline hydrochlorideMeSH
Roche brand OF amitriptyline hydrochlorideMeSH
Chemical FormulaC20H24ClN
Average Molecular Mass313.864 g/mol
Monoisotopic Mass313.160 g/mol
CAS Registry Number549-18-8
IUPAC Namedimethyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine hydrochloride
Traditional Nameamitriptyline hydrochloride
SMILESCl.CN(C)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12
InChI IdentifierInChI=1S/C20H23N.ClH/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20;/h3-6,8-12H,7,13-15H2,1-2H3;1H
InChI KeyKFYRPLNVJVHZGT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassDibenzocycloheptenes
Sub ClassNot Available
Direct ParentDibenzocycloheptenes
Alternative Parents
Substituents
  • Dibenzocycloheptene
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Hydrochloride
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0045 g/LALOGPS
logP5.1ALOGPS
logP4.81ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity101.51 m³·mol⁻¹ChemAxon
Polarizability33.5 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDBSALT000009
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAmitriptyline
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID11065
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References