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Record Information
Version5.0
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 Molecular Properties
PropertyValueReference
Melting Point196 - 197 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0045 g/LNot Available
LogP4.9Not Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M+H]+ExperimentalCBM167.230932474
AllCCS[M+H]+ExperimentalNot Available166.272http://allccs.zhulab.cn/database/detail?ID=AllCCS00000741
DarkChem[M+H]+PredictedNot Available166.10731661259
DarkChem[M-H]-PredictedNot Available166.99831661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9010000000-2afae55587735e5a8ce12017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9010000000-2afae55587735e5a8ce12018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9040000000-fe5eb711e5e29e99efed2017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9210000000-989cd234a8cdf04c5f692014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05po-5890000000-4cce07a2d07337e4ce902017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1590000000-35080e23f36a6ed300052017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-66d4e2dc0e65719c89492017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0190000000-18fad36e219aa0091dcf2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05o3-3980000000-bd3bb65e31837e45268f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aou-2940000000-c3c71a4ddeb15eb427b42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-2930000000-f6bc4a5899aed7b3047e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fr6-2930000000-c348567e54820b6ddff32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-fae7f4e9cc1f20e9a2dd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0190000000-42ecf4fcfbd4bd1023222017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05o3-3980000000-69e1e5d2fdd46de25ba42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aou-2940000000-853a0f18213b600d48ae2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05mo-2930000000-9493535ee63a9a7085272017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fr6-2930000000-fba97ca65c4bf19403852017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1690000000-99ea606fc86c8400c4ce2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-8155764b5e04e44b4ca22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0190000000-7e3a5d063f540759d63f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0apl-0960000000-e35715828f4c02816f192017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0lfu-0940000000-a6befd2c2f6b01d0c3482017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-e92473ae05e0e7ecb6ed2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-3390000000-db46c53d9e4e8729d7f32016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5940000000-1c8f604ddf2e5e56560e2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-90c019b2f9a1e35d9e6d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090000000-a8d8a7f9b985c30547f22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-7290000000-3505755fe83fe73e694f2016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00321 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB 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 ]