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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2018-05-20 20:49:45 UTC
HMDB IDHMDB0014466
Secondary Accession Numbers
  • HMDB14466
Metabolite Identification
Common NameAmitriptyline
DescriptionAmitriptyline hydrochloride is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, amitriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, amitriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Amitriptyline may be used to treat depression, chronic pain (unlabeled use), irritable bowel syndrome (unlabeled use), diabetic neuropathy (unlabeled use), post-traumatic stress disorder (unlabeled use), and for migraine prophylaxis (unlabeled use).
Structure
Thumb
Synonyms
ValueSource
10,11-dihydro-5-(gamma-Dimethylaminopropylidene)-5H-dibenzo(a,D)cyclohepteneChEBI
10,11-dihydro-N,N-Dimethyl-5H-dibenzo(a,D)heptalene-Delta(5),gamma-propylamineChEBI
3-(10,11-dihydro-5H-dibenzo(a,D)Cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamineChEBI
3-(10,11-dihydro-5H-dibenzo[a,D]Cyclohepten-5-ylidene)-N,N-dimethylpropan-1-amineChEBI
5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,D)cycloheptatrieneChEBI
5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,D)cyclohepteneChEBI
5-(gamma-Dimethylaminopropylidene)-5H-dibenzo[a,D][1,4]cycloheptadieneChEBI
AmitriptylinChEBI
10,11-dihydro-5-(g-Dimethylaminopropylidene)-5H-dibenzo(a,D)cyclohepteneGenerator
10,11-dihydro-5-(γ-dimethylaminopropylidene)-5H-dibenzo(a,D)cyclohepteneGenerator
10,11-dihydro-N,N-Dimethyl-5H-dibenzo(a,D)heptalene-delta(5),g-propylamineGenerator
10,11-dihydro-N,N-Dimethyl-5H-dibenzo(a,D)heptalene-δ(5),γ-propylamineGenerator
5-(g-Dimethylaminopropylidene)-5H-dibenzo[a,D][1,4]cycloheptadieneGenerator
5-(γ-dimethylaminopropylidene)-5H-dibenzo[a,D][1,4]cycloheptadieneGenerator
10,11-dihydro-N,N-Dimethyl-5H-dibenzo(a,D)heptalene-δ(5),g-propylamineGenerator
AmitriprolidineHMDB
AmitryptilineHMDB
AmitryptylineHMDB
AmytriptilineHMDB
APS brand OF amitriptyline hydrochlorideMeSH
Amitriptylin betaMeSH
apo-AmitriptylineMeSH
Apotex brand OF amitriptyline hydrochlorideMeSH
Bayer brand OF amitriptyline hydrochlorideMeSH
Desitin, amitriptylinMeSH
DomicalMeSH
Douglas brand OF amitriptyline hydrochlorideMeSH
Goldshield brand OF amitriptyline hydrochlorideMeSH
Merck brand OF amitriptyline hydrochlorideMeSH
Merck sharp and dohme brand OF amitriptyline embonateMeSH
Rodleben brand OF amitriptyline hydrochlorideMeSH
SarotenMeSH
TryptineMeSH
Amitriptylin RPHMeSH
AmitrolMeSH
apo AmitriptylineMeSH
ApoAmitriptylineMeSH
Cahill may roberts brand OF amitriptyline hydrochlorideMeSH
LaroxylMeSH
NovoprotectMeSH
Rhône poulenc rorer brand OF amitriptyline hydrochlorideMeSH
TryptanolMeSH
TryptizolMeSH
beta, AmitriptylinMeSH
Alphapharm brand OF amitriptyline hydrochlorideMeSH
AmitripMeSH
Amitriptylin-neuraxpharmMeSH
AmitriptylinneuraxpharmMeSH
AnapsiqueMeSH
Cahill may roberts brand OF amitriptyline embonateMeSH
DamilenMeSH
Desitin brand OF amitriptyline hydrochlorideMeSH
EndepMeSH
Hexal brand OF amitriptyline hydrochlorideMeSH
Krewel brand OF amitriptyline hydrochlorideMeSH
Protea brand OF amitriptyline hydrochlorideMeSH
Psicofarma brand OF amitriptyline hydrochlorideMeSH
RPH, AmitriptylinMeSH
Rhône-poulenc rorer brand OF amitriptyline hydrochlorideMeSH
Roche brand OF amitriptyline hydrochlorideMeSH
SarotexMeSH
SyneudonMeSH
TriptafenMeSH
AmineurinMeSH
Amitriptylin desitinMeSH
Amitriptylin neuraxpharmMeSH
Amitriptyline hydrochlorideMeSH
Amrad brand OF amitriptyline hydrochlorideMeSH
Betapharm brand OF amitriptyline hydrochlorideMeSH
DDSA brand OF amitriptyline hydrochlorideMeSH
ElavilMeSH
LentizolMeSH
Lundbeck brand OF amitriptyline hydrochlorideMeSH
Merck sharp and dohme brand OF amitriptyline hydrochlorideMeSH
neuro Hexal brand OF amitriptyline hydrochlorideMeSH
Parke davis brand OF amitriptyline hydrochlorideMeSH
Zeneca brand OF amitriptyline hydrochlorideMeSH
Neuraxpharm brand OF amitriptyline hydrochlorideMeSH
Chemical FormulaC20H23N
Average Molecular Weight277.4033
Monoisotopic Molecular Weight277.183049741
IUPAC Namedimethyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine
Traditional Nameamitriptyline
CAS Registry Number50-48-6
SMILES
CN(C)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12
InChI Identifier
InChI=1S/C20H23N/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
InChI KeyKRMDCWKBEZIMAB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dibenzocycloheptenes. These 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
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point196 - 197 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0045 g/LNot Available
LogP4.9Not 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
Polarizability33.74 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9010000000-2afae55587735e5a8ce1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9010000000-2afae55587735e5a8ce1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9040000000-fe5eb711e5e29e99efedView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05po-5890000000-4cce07a2d07337e4ce90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1590000000-35080e23f36a6ed30005View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-66d4e2dc0e65719c8949View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0190000000-18fad36e219aa0091dcfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05o3-3980000000-bd3bb65e31837e45268fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aou-2940000000-c3c71a4ddeb15eb427b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-2930000000-f6bc4a5899aed7b3047eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fr6-2930000000-c348567e54820b6ddff3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-fae7f4e9cc1f20e9a2ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0190000000-42ecf4fcfbd4bd102322View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05o3-3980000000-69e1e5d2fdd46de25ba4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aou-2940000000-853a0f18213b600d48aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-2930000000-9493535ee63a9a708527View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fr6-2930000000-fba97ca65c4bf1940385View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1690000000-99ea606fc86c8400c4ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-8155764b5e04e44b4ca2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0190000000-7e3a5d063f540759d63fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0apl-0960000000-e35715828f4c02816f19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0lfu-0940000000-a6befd2c2f6b01d0c348View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-e92473ae05e0e7ecb6edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-3390000000-db46c53d9e4e8729d7f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5940000000-1c8f604ddf2e5e56560eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-90c019b2f9a1e35d9e6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090000000-a8d8a7f9b985c30547f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-7290000000-3505755fe83fe73e694fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9210000000-989cd234a8cdf04c5f69View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00321 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00321 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00321
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2075
KEGG Compound IDC06824
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmitriptyline
METLIN IDNot Available
PubChem Compound2160
PDB IDTP0
ChEBI ID2666
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Otaka M, Jin M, Odashima M, Matsuhashi T, Wada I, Horikawa Y, Komatsu K, Ohba R, Oyake J, Hatakeyama N, Watanabe S: New strategy of therapy for functional dyspepsia using famotidine, mosapride and amitriptyline. Aliment Pharmacol Ther. 2005 Jun;21 Suppl 2:42-6. [PubMed:15943846 ]