BUTRIPTYLINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H27N
Molecular Weight	293.4458
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(CC1C2=CC=CC=C2CCC3=CC=CC=C13)CN(C)C

InChI

InChIKey=ALELTFCQZDXAMQ-UHFFFAOYSA-N

InChI=1S/C21H27N/c1-16(15-22(2)3)14-21-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)21/h4-11,16,21H,12-15H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C21H27N
Molecular Weight	293.4458
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1036481

Butriptyline is a tricyclic antidepressant used in patients with depression associated with anxiety. The drug is supposed to be withdrawn from the market as the last publication about its clinical use is dated by 1988.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1036481	Primary		Approved 8583	EVADYNE Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
46.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6894708/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		BUTRIPTYLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
20.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6894708/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		BUTRIPTYLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
638.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6894708/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		BUTRIPTYLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
536.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6894708/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		BUTRIPTYLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
19.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6894708/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		BUTRIPTYLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
19.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6894708/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		BUTRIPTYLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
145 mg 1 times / day multiple, oral Studied dose Dose: 145 mg, 1 times / day Route: oral Route: multiple Dose: 145 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6353270/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6353270/	Sources: https://pubmed.ncbi.nlm.nih.gov/6353270/
75 mg single, oral Studied dose Dose: 75 mg Route: oral Route: single Dose: 75 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6894708/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6894708/	Sources: https://pubmed.ncbi.nlm.nih.gov/6894708/
3425 mg single, oral Overdose Dose: 3425 mg Route: oral Route: single Dose: 3425 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7967544/	healthy Health Status: healthy Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7967544/	Disc. AE: death... AEs leading to discontinuation/dose reduction: death (grade 5, 1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/7967544/

AEs

AE	Significance	Dose	Population
death	grade 5, 1 pt Disc. AE	3425 mg single, oral Overdose Dose: 3425 mg Route: oral Route: single Dose: 3425 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7967544/	healthy Health Status: healthy Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7967544/

PubMed

Title	Date	PubMed
Effect of butriptyline on subjective feelings and sleep.	1977-04	193546
Some clinical pharmacological studies with butriptyline, an antidepressive drug.	1977-02	576584
Clinical experience with butriptyline (AY-62014) in the treatment of depressions.	1971	4948364
Report of butriptyline hydrochloride (Evadyne) in ambulatory patients.	1971	4948365
Psychopharmacological evaluation of a new antidepressant: butriptyline.	1969-12	5371184

Sample Use Guides

In Vivo Use Guide

The daily dosage is between 75 and 150 mg/day.

Route of Administration: Oral

In Vitro Use Guide

Butriptyline exhibited rather potent inhibition of 3H-dopamine uptake in rat corpus striatum with IC50 value in the range 10(-6)-10(-5) M.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:20:27 GMT 2025` Edited by `admin` on `Mon Mar 31 18:20:27 GMT 2025`
Record UNII	Z22441975X
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BUTRIPTYLINE

Official Name

English

EVADYNE

Preferred Name

English

(±)-10,11-DIHYDRO-N,N,.BETA.-TRIMETHYL-5H-DIBENZO(A,D)CYCLOHEPTENE-5-PROPYLAMINE

Systematic Name

English

5H-DIBENZO(A,D)CYCLOHEPTENE-5-PROPANAMINE, 10,11-DIHYDRO-N,N,.BETA.-TRIMETHYL-, (±)-

Systematic Name

English

BUTRIPTYLINE [MI]

Common Name

English

butriptyline [INN]

Common Name

English

Butriptyline [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN06AA15