danitracen

{{Short description|Tetracyclic antidepressant}}

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| CAS_number = 1447-70-7

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| PubChem = 35758

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| UNII = SD507F5T2W

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| ChEMBL = 440557

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| IUPAC_name = 4-(6H-benzo[c][1]benzothiepin-11-ylidene)-1-methylpiperidine

| C=20 | H=21 | N=1 | O=1

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| SMILES = CN1CCC(=C2C3=CC=CC=C3C(C4=CC=CC=C42)O)CC1

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| StdInChI = 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

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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 was investigated in clinical trials in depressed patients. At 3 mg/day, danitracen was equipotent to 150 mg/day amitriptyline.{{cite journal | vauthors = Engelhardt G | title = [On the pharmacology of 9,10-dihydro-10-(1-methyl-4-piperidylidene)-9-anthrol (WA 335), a histamine and serotonin antagonist (author's transl)] | language = German | journal = Arzneimittel-Forschung | volume = 25 | issue = 11 | pages = 1723–37 | date = November 1975 | pmid = 1049 | doi = | url = }}{{cite web | title = Danitracen | url = https://drugs.ncats.io/drug/SD507F5T2W | work = Inxight Drugs | publisher = National Center for Advancing Translational Sciences (NCATS) }}{{cite journal | vauthors = Castañer J, Chatterjee SS | date = 1976 | title = Danitracen | journal = Drugs of the Future | volume = 1 | issue = 6) | pages = 279 | doi = 10.1358/dof.1976.001.06.1002525}}{{cite journal | vauthors = Maj J, Baran L, Sowińska H, Gancarczyk L | title = The action of compound WA-335 on the central nervous system | journal = Archivum Immunologiae et Therapiae Experimentalis | volume = 24 | issue = 2 | pages = 205–22 | date = 1976 | pmid = 945051 | doi = | url = }}{{cite journal | vauthors = Maj J, Sowińska H, Baran L | title = Influence of WA-335, a factor which blocks serotonin receptors, on neuroleptic-induced catalepsy | journal = Archivum Immunologiae et Therapiae Experimentalis | volume = 24 | issue = 2 | pages = 197–203 | date = 1976 | pmid = 945050 | doi = | url = }}{{cite journal | vauthors = Matussek N, Benkert O, Fidetzis K, Flach D, Hermann HU, Kaumeier S, Kindt H, Kinzler E, Rüther E, Watzka W | title = [Comparison of the effects of the anthracene derivative danitracen (WA335-BS) and amitriptyline in depressive patients (author's transl)] | language = German | journal = Arzneimittel-Forschung | volume = 26 | issue = 6 | pages = 1160–2 | date = 1976 | pmid = 786311 | doi = | url = }}