Alaproclate

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| IUPAC_name = 1-(4-Chlorophenyl)-2-methylpropan-2-yl 2-aminopropanoate

| image = Alaproclate structure.svg

| image_class = skin-invert-image

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 60719-82-6

| CAS_supplemental =
{{CAS|60719-83-7}} (hydrochloride)

| ATC_prefix = N06

| ATC_suffix = AB07

| PubChem = 2081

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

| ChemSpiderID = 1997

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

| UNII = C4R42570ZO

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

| KEGG = D02787

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

| ChEMBL = 36591

| synonyms = GEA-654; 4-Chloro-α,α-dimethylphenethylalaninate; para-Chloro-α,α-dimethylphenethylalaninate; {{Small|DL}}-Alanine p-chloro-α,α-dimethylphenylethyl ester

| C=13 | H=18 | Cl=1 | N=1 | O=2

| smiles = Clc1ccc(cc1)CC(OC(=O)C(N)C)(C)C

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

| StdInChI = 1S/C13H18ClNO2/c1-9(15)12(16)17-13(2,3)8-10-4-6-11(14)7-5-10/h4-7,9H,8,15H2,1-3H3

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

| StdInChIKey = FZSPJBYOKQPKCD-UHFFFAOYSA-N

}}

Alaproclate (developmental code name GEA-654) is a drug that was being developed as an antidepressant by the Swedish pharmaceutical company Astra AB (now AstraZeneca) in the 1970s.{{cite book | last=Elks | first=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=PA22 | access-date=9 December 2024 | page=22}}

It acts as a selective serotonin reuptake inhibitor (SSRI), and along with zimelidine and indalpine, was one of the first of its kind. Development was discontinued due to the observation of liver complications in rodent studies. In addition to its SSRI properties, alaproclate has been found to act as a non-competitive NMDA receptor antagonist, but does not have discriminative stimulus properties similar to phencyclidine (PCP).{{cite journal |title=Alaproclate acts as a potent, reversible and noncompetitive antagonist of the NMDA receptor coupled ion flow |vauthors =Wilkinson A, Courtney M, Westlind-Danielsson A, Hallnemo G, Akerman KE |journal=The Journal of Pharmacology and Experimental Therapeutics |date=December 1994 |volume=271 |issue=3 |pages=1314–9 |pmid=7996440 |url=http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=7996440 |url-access=subscription }}{{cite journal |title=Evaluation of the phencyclidine-like discriminative stimulus effects of novel NMDA channel blockers in rats |vauthors =Nicholson KL, Balster RL |journal=Psychopharmacology |date=November 2003 |volume=170 |issue=2 |pages=215–24 |pmid=12851738 |doi=10.1007/s00213-003-1527-6|s2cid =30803162 }}

The drug is similar in chemical structure to chlorphentermine, cloforex, and cericlamine, but is not itself a phenethylamine or amphetamine as it has an oxygen atom in place of the amine nitrogen.

Alaproclate was first described in the scientific literature by 1978.