Atiprosin

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 458780782

| IUPAC_name = (4aR,12bS)-1-ethyl-12-methyl-4-(propan-2-yl)-1,2,3,4,4a,5,6,12b-octahydropyrazino[2',3':3,4]pyrido[1,2-a]indole

| image = Atiprosin Structure.svg

| width =

| tradename =

| legal_status =

| routes_of_administration = Oral

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

| CAS_number = 89303-63-9

| ATC_prefix = none

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

| StdInChI = 1S/C20H29N3/c1-5-21-12-13-22(14(2)3)18-10-11-23-17-9-7-6-8-16(17)15(4)19(23)20(18)21/h6-9,14,18,20H,5,10-13H2,1-4H3/t18-,20+/m1/s1

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

| StdInChIKey = WXNVFYIBELASJW-QUCCMNQESA-N

| PubChem = 71770

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

| ChemSpiderID = 64808

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2111172

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

| UNII = ALS52889WF

| synonyms = AY-28,228

| C=20 | H=29 | N=3

| SMILES = n23c1ccccc1c(c2[C@H]4N(CCN([C@@H]4CC3)C(C)C)CC)C

}}

Atiprosin (developmental code name AY-28,228) is an antihypertensive agent which acts as a selective α₁-adrenergic receptor antagonist.{{cite book | author = David J. Triggle | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=DeX7jgInYFMC&q=atiprosin&pg=PA189}}{{cite journal |vauthors=Jirkovsky I, Santroch G, Baudy R, Oshiro G | title = Octahydropyrazino[2',3':3,4]pyrido[1,2-a]indoles. A new class of potent antihypertensive agents | journal = Journal of Medicinal Chemistry | volume = 30 | issue = 2 | pages = 388–94 |date=February 1987 | pmid = 3806618 | doi = 10.1021/jm00385a022}}{{cite journal |vauthors=Grimes D, Rimele TJ, Henry DE | title = In vitro isolated tissue studies with atiprosin (AY-28,228): a new antihypertensive compound | journal = Journal of Cardiovascular Pharmacology | volume = 10 | issue = 3 | pages = 249–58 |date=September 1987 | pmid = 2444771 | doi = 10.1097/00005344-198709000-00001| s2cid = 9361176 |display-authors=etal| doi-access = free }}{{cite journal |vauthors=Oshiro G, Wojdan A, Klein M, Metcalf G | title = Antihypertensive and hypotensive actions of atiprosin (AY-28,228) in rats, dogs, and monkeys | journal = Journal of Cardiovascular Pharmacology | volume = 10 | issue = 3 | pages = 341–9 |date=September 1987 | pmid = 2444784 | doi = 10.1097/00005344-198709000-00014| s2cid = 19086175 | doi-access = free }} It also possesses some antihistamine activity, though it is some 15-fold weaker in this regard than as an alpha blocker. It was never marketed.