Aptazapine

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 457812421

| IUPAC_name = 2-methyl-1,3,4,14b-tetrahydro-2H,10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine

| image = Aptazapine.svg

| width = 200px

| tradename =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 71576-40-4

| ATC_prefix = none

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 336712

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = MNHDDERDSNZCCK-UHFFFAOYSA-N

| PubChem = 51355

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 46513

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 240J927J1R

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02972

| C=16 | H=19 | N=3

| SMILES = c42c(N3C(c1cccn1C2)CN(CC3)C)cccc4

}}

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.{{cite journal |vauthors=Liebman JM, Lovell RA, Braunwalder A | title = CGS 7525A, a new, centrally active alpha 2 adrenoceptor antagonist | journal = Life Sciences | volume = 32 | issue = 4 | pages = 355–63 |date=January 1983 | pmid = 6131367 | doi = 10.1016/0024-3205(83)90081-4|display-authors=etal}}{{cite book | author = Author Unknown | title = Annual Reports in Medicinal Chemistry (Volume 20) | publisher = Academic Press | location = Boston | year = 1985 | pages = 352 | isbn = 0-12-040520-2 | url = https://books.google.com/books?id=j-3Cd_SWIksC&q=aptazapine&pg=PA33}}{{cite book | author = David J. Triggle | title = Dictionary of pharmacological agents | publisher = Chapman & Hall | location = London | year = 1997 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=DeX7jgInYFMC&q=aptazapine&pg=PA167}} 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.{{cite journal |vauthors=Gower AJ, Broekkamp CL, Rijk HW, Van Delft AM | title = 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 | journal = Archives Internationales de Pharmacodynamie et de Thérapie | volume = 291 | pages = 185–201 | year = 1988 | pmid = 2896489 }} Based on its pharmacological profile, aptazapine may be classified as a noradrenergic and specific serotonergic antidepressant (NaSSA).