DANITRACEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H21NO
Molecular Weight	291.3868
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCC(CC1)=C2C3=CC=CC=C3C(O)C4=CC=CC=C24

InChI

InChIKey=HLBRHTFSMMEHPK-UHFFFAOYSA-N

InChI=1S/C20H21NO/c1-21-12-10-14(11-13-21)19-15-6-2-4-8-17(15)20(22)18-9-5-3-7-16(18)19/h2-9,20,22H,10-13H2,1H3

HIDE SMILES / InChI

Molecular Formula	C20H21NO
Molecular Weight	291.3868
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/309138 | https://www.ncbi.nlm.nih.gov/pubmed/6176681 | https://www.ncbi.nlm.nih.gov/pubmed/401705

Danitracen (WA 335) is an antidepressant compound developed in the 1970s. Danitracen acts by blocking central and peripheral 5-HT receptors: it potentiates testosterone-induced sexual behavior in rats and abolishes the 5-hydroxytryptophan (5-HTP) induced hypermotility in mice. In amphetamine-treated rats, administration of danitracen lowered whole brain serotonin and norepinephrine levels. Danitracen investigated in clinical trials in depressed patients. At 3 mg/day, danitracen was equipotent to 150 mg/day amitriptyline.

Approval Year

PubMed

Title	Date	PubMed
Chronic treatment with antidepressant drugs: potentiation of apomorphine-induced aggressive behaviour in rats.	1979-08	575199
The action of compound WA-335 on the central nervous system.	1976	945051
Influence of WA-335, a factor which blocks serotonin receptors, on neuroleptic-induced catalepsy.	1976	945050
[Comparison of the effects of the anthracene derivative danitracen (WA335-BS) and amitriptyline in depressive patients (author's transl)].	1976	786311
[Central action of WA-335-BS, a substance with peripheral antiserotonin and antihistaminic activity].	1975-11	1050
[On the pharmacology of 9,10-dihydro-10-(1-methyl-4-piperidylidene)-9-anthrol (WA 335), a histamine and serotonin antagonist (author's transl)].	1975-11	1049

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:05:10 GMT 2025` Edited by `admin` on `Wed Apr 02 09:05:10 GMT 2025`
Record UNII	SD507F5T2W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-170955

Preferred Name

English

DANITRACEN

Official Name

English

W-A 335

Code

English

danitracen [INN]

Common Name

English

9,10-DIHYDRO-10-(1-METHYL-4-PIPERIDYLIDENE)-9-ANTHROL

Systematic Name

English

WA-335

Code

English

W-A-335

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C66885