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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:43 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
Data?1582753183
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
LaroxylKegg
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-propylamineHMDB
AmitriprolidineHMDB
AmitryptilineHMDB
AmitryptylineHMDB
AmytriptilineHMDB
APS brand OF amitriptyline hydrochlorideHMDB
Amitriptylin betaHMDB
Apo-amitriptylineHMDB
Apotex brand OF amitriptyline hydrochlorideHMDB
Bayer brand OF amitriptyline hydrochlorideHMDB
Desitin, amitriptylinHMDB
DomicalHMDB
Douglas brand OF amitriptyline hydrochlorideHMDB
Goldshield brand OF amitriptyline hydrochlorideHMDB
Merck brand OF amitriptyline hydrochlorideHMDB
Merck sharp and dohme brand OF amitriptyline embonateHMDB
Rodleben brand OF amitriptyline hydrochlorideHMDB
SarotenHMDB
TryptineHMDB
Amitriptylin RPHHMDB
AmitrolHMDB
Apo amitriptylineHMDB
ApoAmitriptylineHMDB
Cahill may roberts brand OF amitriptyline hydrochlorideHMDB
NovoprotectHMDB
Rhône poulenc rorer brand OF amitriptyline hydrochlorideHMDB
TryptanolHMDB
TryptizolHMDB
beta, AmitriptylinHMDB
Alphapharm brand OF amitriptyline hydrochlorideHMDB
AmitripHMDB
Amitriptylin-neuraxpharmHMDB
AmitriptylinneuraxpharmHMDB
AnapsiqueHMDB
Cahill may roberts brand OF amitriptyline embonateHMDB
DamilenHMDB
Desitin brand OF amitriptyline hydrochlorideHMDB
EndepHMDB
Hexal brand OF amitriptyline hydrochlorideHMDB
Krewel brand OF amitriptyline hydrochlorideHMDB
Protea brand OF amitriptyline hydrochlorideHMDB
Psicofarma brand OF amitriptyline hydrochlorideHMDB
RPH, AmitriptylinHMDB
Rhône-poulenc rorer brand OF amitriptyline hydrochlorideHMDB
Roche brand OF amitriptyline hydrochlorideHMDB
SarotexHMDB
SyneudonHMDB
TriptafenHMDB
AmineurinHMDB
Amitriptylin desitinHMDB
Amitriptylin neuraxpharmHMDB
Amitriptyline hydrochlorideHMDB
Amrad brand OF amitriptyline hydrochlorideHMDB
Betapharm brand OF amitriptyline hydrochlorideHMDB
DDSA brand OF amitriptyline hydrochlorideHMDB
ElavilHMDB
LentizolHMDB
Lundbeck brand OF amitriptyline hydrochlorideHMDB
Merck sharp and dohme brand OF amitriptyline hydrochlorideHMDB
Neuro hexal brand OF amitriptyline hydrochlorideHMDB
Parke davis brand OF amitriptyline hydrochlorideHMDB
Zeneca brand OF amitriptyline hydrochlorideHMDB
Neuraxpharm brand OF amitriptyline hydrochlorideHMDB
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
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
  • 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9010000000-2afae55587735e5a8ce1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9010000000-2afae55587735e5a8ce1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9040000000-fe5eb711e5e29e99efedSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05po-5890000000-4cce07a2d07337e4ce90Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1590000000-35080e23f36a6ed30005Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-66d4e2dc0e65719c8949Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0190000000-18fad36e219aa0091dcfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05o3-3980000000-bd3bb65e31837e45268fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aou-2940000000-c3c71a4ddeb15eb427b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-2930000000-f6bc4a5899aed7b3047eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fr6-2930000000-c348567e54820b6ddff3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-fae7f4e9cc1f20e9a2ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0190000000-42ecf4fcfbd4bd102322Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05o3-3980000000-69e1e5d2fdd46de25ba4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aou-2940000000-853a0f18213b600d48aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-2930000000-9493535ee63a9a708527Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fr6-2930000000-fba97ca65c4bf1940385Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1690000000-99ea606fc86c8400c4ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-8155764b5e04e44b4ca2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0190000000-7e3a5d063f540759d63fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0apl-0960000000-e35715828f4c02816f19Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0lfu-0940000000-a6befd2c2f6b01d0c348Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-e92473ae05e0e7ecb6edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-3390000000-db46c53d9e4e8729d7f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5940000000-1c8f604ddf2e5e56560eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-90c019b2f9a1e35d9e6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090000000-a8d8a7f9b985c30547f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-7290000000-3505755fe83fe73e694fSpectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9210000000-989cd234a8cdf04c5f69Spectrum
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2075
KEGG Compound IDC06824
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmitriptyline
METLIN IDNot Available
PubChem Compound2160
PDB IDNot Available
ChEBI ID2666
Food Biomarker OntologyNot Available
VMH IDNot Available
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 ]