Amitriptyline

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H23N
Molecular Weight	277.4033
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCC=C1C2=C(CCC3=C1C=CC=C3)C=CC=C2

InChI

InChIKey=KRMDCWKBEZIMAB-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C20H23N
Molecular Weight	277.4033
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.emedexpert.com/facts/amitriptyline-facts.shtml
Curator's Comment: description was created based on several sources, including http://www.rxlist.com/elavil-drug.htm https://www.ncbi.nlm.nih.gov/pubmed/23235671; https://www.ncbi.nlm.nih.gov/pubmed/11157426; http://www.ncbi.nlm.nih.gov/pubmed/16871467; http://www.ncbi.nlm.nih.gov/pubmed/2578912; http://www.ncbi.nlm.nih.gov/pubmed/?term=15943846

Amitriptyline is a derivative of dibenzocycloheptadiene and a tricyclic antidepressant (TCA) and is mainly used to treat symptoms of depression. It works on the central nervous system (CNS) by inhibiting the membrane pump mechanism responsible for uptake of norepinephrine and serotonin in adrenergic and serotonergic neurons. Amitriptyline has been frequently used as an active comparator in clinical trials on newer antidepressants. It is rarely used as a first-line antidepressant nowadays due to its high degree of toxicity in overdose and generally poorer tolerability than the newer antidepressants.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Sodium-dependent noradrenaline transporter 39 Target ID: P23975 Gene ID: 6530.0 Gene Symbol: SLC6A2 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/14744476	Inhibitor 8504	3.45 nM [IC50]
Sodium-dependent serotonin transporter 41 Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/14744476	Inhibitor 8504	13.3 nM [IC50]
5-hydroxytryptamine receptor 2A 73 Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/7855217	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depressive disorder 4 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=1e6d2c80-fbc8-444e-bdd3-6a91fe1b95bd	Preventing		Approved 8583	AMITRIPTYLINE HYDROCHLORIDE Approved Use For the relief of symptoms of depression. Endogenous depression is more likely to be alleviated than are other depressive states. Launch Date 1997

C_max

Value	Dose	Co-administered	Analyte	Population
15.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10383563	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		AMITRIPTYLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
593 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10383563	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		AMITRIPTYLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
20.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10383563	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		AMITRIPTYLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
7.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6125396	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:		AMITRIPTYLINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP2C8 1057 OCT1 620 OCT2 779	CYP1A2 1197 CYP2C19 1119 CYP2B6 776 UGT2B10 131 UGT1A4 399

Drug as perpetrator

Target	Modality	Activity
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19002438/	yes [IC50 14 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20567254/	yes [IC50 6.99 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16415122/	yes [IC50 8.8 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2015019/	yes [Inhibition 200 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12228186/	yes [Ki 31 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12228186/	yes [Ki 37.7 uM]

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2042727/	no
CYP2C19 1119	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2042727/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11259560/	yes
CYP2C9 1193	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2042727/	yes
CYP2D6 1388	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2042727/	yes
CYP3A4 1946	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2042727/	yes
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20133892/	yes
UGT2B10 131	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20133892/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1571977/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2666	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2666
eMolecules	739635	https://www.emolecules.com/cgi-bin/more?vid=739635
MolPort	MolPort-001-662-651	https://www.molport.com/shop/molecule-link/MolPort-001-662-651
ZINC	ZINC000000968257	http://zinc15.docking.org/substances/ZINC000000968257

PubMed

Title	Date	PubMed
[Individual conditions of pharmacogenic confusion conditions. Comparison of amitriptyline and clozapine].	1976	1019368
Comparison of the effects of antidepressants and their metabolites on reuptake of biogenic amines and on receptor binding.	1999 Aug	10379421
[Hypotension refractory to ephedrine after sympathetic blockade in a patient on long-term therapy with tricyclic antidepressants].	1999 Oct	10563144
Gender differences in depression associated with neurologic illness: clinical correlates and pharmacologic response.	2001	11480103
A randomized trial of fluoxetine versus amitriptyline in musculo-skeletal pain.	2001	11475920
Long-term effects of tricyclic antidepressants on norepinephrine kinetics in humans.	2001	11341486
The concentration of three anti-seizure medications in hair: the effects of hair color, controlling for dose and age.	2001	11339881
Dopaminergic activity in transgenic mice underexpressing glucocorticoid receptors: effect of antidepressants.	2001	11226678
Evidence for the use of gabapentin in the treatment of diabetic peripheral neuropathy.	2001 Apr	11354388
The effects of amitriptyline, citalopram and reboxetine on autonomic nervous system. A randomised placebo-controlled study on healthy volunteers.	2001 Apr	11349386
Noradrenergic dysfunction and antidepressant treatment response.	2001 Apr	11313162
[Sensory neuropathy in HIV infection: pathogenesis and therapy].	2001 Apr 14	11332255
Controlling phantom limb pain in Sierra Leone.	2001 Apr 21	11418165
Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates.	2001 Aug	11505218
Amitriptyline treatment in chronic drug-induced headache: a double-blind comparative pilot study.	2001 Feb	11251703
Antidepressant treatment and global tests of coagulation and fibrinolysis.	2001 Feb	11247103
Transplacental transfer of amitriptyline and nortriptyline in isolated perfused human placenta.	2001 Feb	11243492
Gabapentin for the treatment of tinnitus: a case report.	2001 Feb	11233342
Cromolyn cream for recalcitrant idiopathic vulvar vestibulitis: results of a placebo controlled study.	2001 Feb	11158692
Amitriptyline v. the rest: still the leading antidepressant after 40 years of randomised controlled trials.	2001 Feb	11157426
Amitriptyline: still efficacious, but at what cost?	2001 Feb	11157421
Serum levels of amitriptyline and therapeutic effect in non-delusional moderately to severely depressed in-patients: a therapeutic window relationship.	2001 Jan	11229620
[Non-fatal effect of highly toxic amitriptyline level after suicide attempt. A case report].	2001 Jan	11221556
Weight outcomes among antidepressant users in nursing facilities.	2001 Jan	11207842
Effect of drugs used for neuropathic pain management on tetrodotoxin-resistant Na(+) currents in rat sensory neurons.	2001 Jan	11135733
Amitriptyline enhances the central component of physiological tremor.	2001 Jan	11118252
Lamotrigine for central poststroke pain: a randomized controlled trial.	2001 Jan 23	11160953
Late-onset GM2 gangliosidosis presenting as burning dysesthesias.	2001 Jul	11483398
[Ciguatera: clinical relevance of a marine neurotoxin].	2001 Jul 13	11499263
The effect of amitriptyline on pain intensity and perception of stress in bruxers.	2001 Jun	11512111
Assessment of DNA damage in C6 glioma cells after antidepressant treatment using an alkaline comet assay.	2001 Jun	11482523
Ring flexibility within tricyclic antidepressant drugs.	2001 Jun	11357174
Effects of amitriptyline on diurnal variations of oxidation-reduction enzyme activities in rat lymphocytes during experimental desynchronosis.	2001 May	11550063
Treatment of neuropathic pain with venlafaxine.	2001 May	11346061
Advances in the management of neuropathic pain.	2001 May	11345017
Inhibition of synovial plasma extravasation by preemptive administration of an antiinflammatory irrigation solution in the rat knee.	2001 May	11323366
Patterns of response to repeated total sleep deprivations in depression.	2001 May	11313092
Combining psychotherapy and antidepressants in the treatment of depression.	2001 May	11313088
High-performance liquid chromatographic method combining radiochemical and ultraviolet detection for determination of low activities of uridine 5'-diphosphate-glucuronosyltransferase.	2001 May 15	11355849
Management of chronic tension-type headache with tricyclic antidepressant medication, stress management therapy, and their combination: a randomized controlled trial.	2001 May 2	11325322
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.	2001 Oct	11561066
Efficacy of spinal manipulation for chronic headache: a systematic review.	2001 Sep	11562654
Drug use and five-year incidence of age-related cataracts: The Beaver Dam Eye Study.	2001 Sep	11535471
Antidepressants as risk factor for ischaemic heart disease: case-control study in primary care.	2001 Sep 22	11566831
Amitriptyline is a potent blocker of human Kv1.1 and Kv7.2/7.3 channels.	2007 May	17456683
Intersegmental vessel formation in zebrafish: requirement for VEGF but not BMP signalling revealed by selective and non-selective BMP antagonists.	2010 Sep	20718746

Patents

Sample Use Guides

In Vivo Use Guide

For outpatients, 75 mg of amitriptyline HCl a day in divided doses. If necessary, this may be increased to a total of 150 mg per day. An alternate method of initiating therapy in outpatients is to begin with 50 to 100 mg amitriptyline HCl at bedtime. This may be increased by 25 or 50 mg as necessary in the bedtime dose to a total of 150 mg per day. Hospitalized patients may require 100 mg a day initially. This can be increased gradually to 200 mg a day if necessary up to 300 mg a day. Not recommended for patients under 12 years of age

Route of Administration: Oral

In Vitro Use Guide

Amitriptyline was used at 40 uM in isolated rat hepatocytes for 60,120,180 min.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:57:00 GMT 2025` Edited by `admin` on `Wed Apr 02 09:57:00 GMT 2025`
Record UNII	1806D8D52K
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LAROXYL

Preferred Name

English

Amitriptyline

Official Name

English

1-PROPANAMINE, 3-(10,11-DIHYDRO-5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-N,N-DIMETHYL-

Systematic Name

English

3-(10,11-DIHYDRO-5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-N,N-DIMETHYL-1-PROPANAMINE

Systematic Name

English

AMITRIPTYLINE [USP IMPURITY]

Common Name

English

AMITRIPTYLINE [MI]

Common Name

English

AMITRIPTYLINE [VANDF]

Common Name

English

amitriptyline [INN]

Common Name

English

NORTRIPTYLINE HYDROCHLORIDE IMPURITY F [EP IMPURITY]

Common Name

English

Amitriptyline [WHO-DD]

Common Name

English

AMITRIPTYLINE [MART.]

Common Name

English

SEROTEN

Common Name

English

PROHEPTADIENE

Common Name

English

TRIPTANOL

Common Name

English

DAMITRIPTYLINE

Common Name

English

FLAVYL

Common Name

English

Classification Tree Code System Code

WHO-ATC

N06CA01

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

WHO-ESSENTIAL MEDICINES LIST

24.2.1

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

FDA ORPHAN DRUG

288809

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

WHO-VATC

QN06AA09

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

LIVERTOX

NBK548410

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

NDF-RT

N0000175752

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

FDA ORPHAN DRUG

739620

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

WHO-ESSENTIAL MEDICINES LIST

8.4

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

NCI_THESAURUS

C94727

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

WHO-VATC

QN06CA01

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

WHO-ATC

N06AA09

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

Code System Code Type Description

MESH

D000639

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

PRIMARY

LACTMED

Amitriptyline

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

PRIMARY

SMS_ID

100000092029

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

PRIMARY

WIKIPEDIA

AMITRIPTYLINE

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

PRIMARY

HSDB

3007

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

PRIMARY

INN

976

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

PRIMARY

PUBCHEM

2160

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

PRIMARY

IUPHAR

200

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

PRIMARY

CAS

50-48-6

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PRIMARY

EVMPD

SUB05462MIG

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

PRIMARY

CHEBI

2666

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

PRIMARY

MERCK INDEX

m1753

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

PRIMARY

Merck Index

NCI_THESAURUS

C62005

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PRIMARY

RXCUI

704

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

PRIMARY

RxNorm

ChEMBL

CHEMBL629

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

PRIMARY

FDA UNII

1806D8D52K

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

PRIMARY

EPA CompTox

DTXSID7022594

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

PRIMARY

DRUG BANK

DB00321

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

PRIMARY

DRUG CENTRAL

180

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

PRIMARY

DAILYMED

1806D8D52K

Created by admin on Wed Apr 02 09:57:01 GMT 2025 , Edited by admin on Wed Apr 02 09:57:01 GMT 2025

PRIMARY

ECHA (EC/EINECS)

200-041-6

Created by admin on Wed Apr 02 09:57:00 GMT 2025 , Edited by admin on Wed Apr 02 09:57:00 GMT 2025

PRIMARY

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ACTIVE MOIETY

Amount:

Name	Property Type	Parameters
Volume of Distribution	PHARMACOKINETIC

Volume of Distribution	PHARMACOKINETIC

MAXIMUM TOLERATED DOSE	TOXICITY	DEPRESSION, INPATIENTS: 300 MG/DAY

Route of Elimination	PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator