alpertine

{{Short description|Abandoned antipsychotic}}

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| image = Alpertine.svg

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| CAS_number = 27076-46-6

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| PubChem = 166547

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| ChemSpiderID = 145751

| UNII = KYT38QTB4K

| KEGG = D02635

| ChEBI = 177808

| ChEMBL = 2104031

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| synonyms = WIN31665; WIN-31,665; Win 31665

| IUPAC_name = ethyl 5,6-dimethoxy-3-[2-(4-phenylpiperazin-1-yl)ethyl]-1H-indole-2-carboxylate

| C=25 | H=31 | N=3 | O=4

| SMILES = CCOC(=O)C1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4

| StdInChI = 1S/C25H31N3O4/c1-4-32-25(29)24-19(20-16-22(30-2)23(31-3)17-21(20)26-24)10-11-27-12-14-28(15-13-27)18-8-6-5-7-9-18/h5-9,16-17,26H,4,10-15H2,1-3H3

| StdInChIKey = RXAVJRAUFOPBOO-UHFFFAOYSA-N

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Alpertine ({{Abbrlink|INN|International Nonproprietary Name}}, {{Abbrlink|USAN|United States Adopted Name}}; developmental code name WIN-31665) is a drug of the pertine group described as an antipsychotic, neuroleptic, and tranqulizer which was never marketed.{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA33 | access-date=30 October 2024 | page=33}}{{cite book | title=Pharmaceutical Manufacturing Encyclopedia | publisher=William Andrew Publishing | series=Volumes 1-4 | year=2013 | isbn=978-0-8155-1856-3 | url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA185 | access-date=30 October 2024 | pages=185–186}}{{cite book | vauthors = Milne GW | title=Drugs: Synonyms and Properties | publisher=Wiley | year=2002 | isbn=978-0-566-08491-1 | url=https://books.google.com/books?id=QxcoEAAAQBAJ&pg=PA422 | access-date=30 October 2024 | page=422}}

Structurally, it is a substituted tryptamine and a piperazinylethylindole.{{cite book | vauthors = Ellis GP, Luscombe DK | title=Progress in Medicinal Chemistry | publisher=Elsevier Science | issue=v. 33 | year=1996 | isbn=978-0-08-086281-1 | url=https://books.google.com/books?id=SDaZ4qcemf8C&pg=PA219 | access-date=30 October 2024 | page=219 | quote=Pertines (class 7; Table 5.12) The pertines oxypertine, solypertine, milipertine, and alpertine are piperazinylethylindoles.}} The drug is closely structurally related to other "pertines" including milipertine, oxypertine, and solypertine, which are also tryptamines and piperazinylethylindoles.

The related drug oxypertine shows high affinity for the serotonin 5-HT₂ and dopamine D₂ receptors (K_i = 8.6{{nbsp}}nM and 30{{nbsp}}nM, respectively) and is also known to act as a catecholamine depleting agent.{{cite journal | vauthors = Megens AA, Kennis LE | title = Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent? | journal = Progress in Medicinal Chemistry | volume = 33 | issue = | pages = 185–232 | date = 1996 | pmid = 8776944 | doi = 10.1016/s0079-6468(08)70306-0 | isbn = 978-0-444-82310-6 }}{{cite journal | vauthors = Bak IJ, Hassler R, Kim JS | title = Differential monoamine depletion by oxypertine in nerve terminals. Granulated synaptic vesicles in relation to depletion of norepinephrine, dopamine and serotonin | journal = Zeitschrift für Zellforschung und Mikroskopische Anatomie | volume = 101 | issue = 3 | pages = 448–462 | year = 1969 | pmid = 5362847 | doi = 10.1007/BF00335580 | s2cid = 32583722 }} Oxypertine, milipertine, and solypertine all antagonize the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.{{cite journal | vauthors = Niemegeers CJ, Janssen PA | title = A systematic study of the pharmacological activities of dopamine antagonists | journal = Life Sciences | volume = 24 | issue = 24 | pages = 2201–2216 | date = June 1979 | pmid = 388130 | doi = 10.1016/0024-3205(79)90096-1 | publisher = Elsevier BV }} Conversely however, alpertine was not effective, at least at doses of up to 10{{nbsp}}mg/kg. ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be a metabolite of the related drugs milipertine and oxypertine.{{cite journal | vauthors = Elliott S | title = Current awareness of piperazines: pharmacology and toxicology | journal = Drug Testing and Analysis | volume = 3 | issue = 7–8 | pages = 430–438 | date = 2011 | pmid = 21744514 | doi = 10.1002/dta.307 | quote = Furthermore, oMeOPP is a metabolite of some prescribed drugs: enciprazione, milipertine, urapidil, dropropizine and oxypertine.[1,47] }}{{cite journal | vauthors = Caccia S, Notarnicola A, Fong MH, Benfenati E | title = Identification and quantitation of 1-arylpiperazines, metabolites resulting from side-chain cleavage of (4-substituted aryl-1-piperazinyl)alkyl heterocyclic derivatives in rat plasma and brain | journal = Journal of Chromatography | volume = 283 | issue = | pages = 211–221 | date = January 1984 | pmid = 6707118 | doi = 10.1016/s0021-9673(00)96256-3 }}

Alpertine was first described in the scientific literature by 1971.