Aptazapine

Aptazapine
Clinical data
ATC code	none;
Identifiers
	IUPAC name 2-methyl-1,3,4,14b-tetrahydro-2H,10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine;
CAS Number	71576-40-4 ;
PubChem CID	51355;
ChemSpider	46513 ;
UNII	240J927J1R;
KEGG	D02972 ;
ChEMBL	ChEMBL336712 ;
CompTox Dashboard (EPA)	DTXSID40868020 ;
Chemical and physical data
Formula	C16H19N3
Molar mass	253.349 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c42c(N3C(c1cccn1C2)CN(CC3)C)cccc4;
	InChI InChI=1S/C16H19N3/c1-17-9-10-19-14-6-3-2-5-13(14)11-18-8-4-7-15(18)16(19)12-17/h2-8,16H,9-12H2,1H3 ; Key:MNHDDERDSNZCCK-UHFFFAOYSA-N ;
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Aptazapine (developmental code name CGS-7525A) is a tetracyclic antidepressant (TeCA) that was assayed in clinical trials for the treatment of depression in the 1980s but was never marketed.^[1]^[2]^[3] It is a potent α₂-adrenergic receptor antagonist with about 10 times the strength of the related compound mianserin and has also been shown to act as a 5-HT₂ receptor antagonist and H₁ receptor inverse agonist, while having no significant effects on the reuptake of serotonin or norepinephrine.^[1]^[4] Based on its pharmacological profile, aptazapine may be classified as a noradrenergic and specific serotonergic antidepressant (NaSSA).

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[1]
Liebman JM, Lovell RA, Braunwalder A, et al. (January 1983). "CGS 7525A, a new, centrally active alpha 2 adrenoceptor antagonist". Life Sciences. 32 (4): 355–63. doi:10.1016/0024-3205(83)90081-4. PMID 6131367.
[2]
Author Unknown (1985). Annual Reports in Medicinal Chemistry (Volume 20). Boston: Academic Press. p. 352. ISBN 0-12-040520-2. {{cite book}}: |author= has generic name (help)
[3]
David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
[4]
Gower AJ, Broekkamp CL, Rijk HW, Van Delft AM (1988). "Pharmacological evaluation of in vivo tests for alpha 2-adrenoceptor blockade in the central nervous system and the effects of the enantiomers of mianserin and its aza-analog ORG 3770". Archives Internationales de Pharmacodynamie et de Thérapie. 291: 185–201. PMID 2896489.

See also

Clinical data

ATC code	none
Identifiers
IUPAC name 2-methyl-1,3,4,14b-tetrahydro-2H,10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine
CAS Number	71576-40-4^N
PubChem CID	51355
ChemSpider	46513^Y
UNII	240J927J1R
KEGG	D02972^Y
ChEMBL	ChEMBL336712^Y
CompTox Dashboard (EPA)	DTXSID40868020
Chemical and physical data
Formula	C₁₆H₁₉N₃
Molar mass	253.349 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c42c(N3C(c1cccn1C2)CN(CC3)C)cccc4
InChI InChI=1S/C16H19N3/c1-17-9-10-19-14-6-3-2-5-13(14)11-18-8-4-7-15(18)16(19)12-17/h2-8,16H,9-12H2,1H3^Y Key:MNHDDERDSNZCCK-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)