Danitracen

Danitracen
Identifiers
	IUPAC name 4-(6H-benzo[c][1]benzothiepin-11-ylidene)-1-methylpiperidine;
CAS Number	1447-70-7;
PubChem CID	121108;
UNII	SD507F5T2W;
ChEMBL	ChEMBL440557;
CompTox Dashboard (EPA)	DTXSID70185156 ;
Chemical and physical data
Formula	C20H21NS
Molar mass	307.46 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC(=C2C3=CC=CC=C3CSC4=CC=CC=C42)CC1;
	InChI InChI=InChI=1S/C20H21NS/c1-21-12-10-15(11-13-21)20-17-7-3-2-6-16(17)14-22-19-9-5-4-8-18(19)20/h2-9H,10-14H2,1H3; Key:MBGXTYVKSKOCFX-UHFFFAOYSA-N;

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.^[1]^[2]^[3]^[4]^[5]^[6]

References

^ Engelhardt G (November 1975). "[On the pharmacology of 9,10-dihydro-10-(1-methyl-4-piperidylidene)-9-anthrol (WA 335), a histamine and serotonin antagonist (author's transl)]". Arzneimittel-Forschung (in German). 25 (11): 1723–37. PMID 1049.
^ "Danitracen". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS).
^ Castañer J, Chatterjee SS (1976). "Danitracen". Drugs of the Future. 1 (6)): 279. doi:10.1358/dof.1976.001.06.1002525.
^ Maj J, Baran L, Sowińska H, Gancarczyk L (1976). "The action of compound WA-335 on the central nervous system". Archivum Immunologiae et Therapiae Experimentalis. 24 (2): 205–22. PMID 945051.
^ Maj J, Sowińska H, Baran L (1976). "Influence of WA-335, a factor which blocks serotonin receptors, on neuroleptic-induced catalepsy". Archivum Immunologiae et Therapiae Experimentalis. 24 (2): 197–203. PMID 945050.
^ Matussek N, Benkert O, Fidetzis K, Flach D, Hermann HU, Kaumeier S, et al. (1976). "[Comparison of the effects of the anthracene derivative danitracen (WA335-BS) and amitriptyline in depressive patients (author's transl)]". Arzneimittel-Forschung (in German). 26 (6): 1160–2. PMID 786311.

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[pmid1049-1] Engelhardt G (November 1975). "[On the pharmacology of 9,10-dihydro-10-(1-methyl-4-piperidylidene)-9-anthrol (WA 335), a histamine and serotonin antagonist (author's transl)]". Arzneimittel-Forschung (in German). 25 (11): 1723–37. PMID 1049.

[2] "Danitracen". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS).

[3] Castañer J, Chatterjee SS (1976). "Danitracen". Drugs of the Future. 1 (6)): 279. doi:10.1358/dof.1976.001.06.1002525.

[pmid945051-4] Maj J, Baran L, Sowińska H, Gancarczyk L (1976). "The action of compound WA-335 on the central nervous system". Archivum Immunologiae et Therapiae Experimentalis. 24 (2): 205–22. PMID 945051.

[pmid945050-5] Maj J, Sowińska H, Baran L (1976). "Influence of WA-335, a factor which blocks serotonin receptors, on neuroleptic-induced catalepsy". Archivum Immunologiae et Therapiae Experimentalis. 24 (2): 197–203. PMID 945050.

[pmid786311-6] Matussek N, Benkert O, Fidetzis K, Flach D, Hermann HU, Kaumeier S, et al. (1976). "[Comparison of the effects of the anthracene derivative danitracen (WA335-BS) and amitriptyline in depressive patients (author's transl)]". Arzneimittel-Forschung (in German). 26 (6): 1160–2. PMID 786311.

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[2]

[3]

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[5]

[6]

Identifiers

IUPAC name 4-(6H-benzo[c][1]benzothiepin-11-ylidene)-1-methylpiperidine
CAS Number	1447-70-7
PubChem CID	121108
UNII	SD507F5T2W
ChEMBL	ChEMBL440557
CompTox Dashboard (EPA)	DTXSID70185156
Chemical and physical data
Formula	C₂₀H₂₁NS
Molar mass	307.46 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1CCC(=C2C3=CC=CC=C3CSC4=CC=CC=C42)CC1
InChI InChI=InChI=1S/C20H21NS/c1-21-12-10-15(11-13-21)20-17-7-3-2-6-16(17)14-22-19-9-5-4-8-18(19)20/h2-9H,10-14H2,1H3 Key:MBGXTYVKSKOCFX-UHFFFAOYSA-N

Danitracen

See also

References