Alaproclate

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.^[1]

Other namesGEA-654; 4-Chloro-α,α-dimethylphenethylalaninate; para-Chloro-α,α-dimethylphenethylalaninate; DL-Alanine p-chloro-α,α-dimethylphenylethyl ester

Routes of
administrationOral

ATC code

• N06AB07 (WHO)

Legal status

• In general: uncontrolled

Quick facts Clinical data, Other names ...

Alaproclate

Clinical data
Other names	GEA-654; 4-Chloro-α,α-dimethylphenethylalaninate; para-Chloro-α,α-dimethylphenethylalaninate; DL-Alanine p-chloro-α,α-dimethylphenylethyl ester
Routes of administration	Oral
ATC code	N06AB07 (WHO)
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 1-(4-Chlorophenyl)-2-methylpropan-2-yl 2-aminopropanoate
CAS Number	60719-82-6 Y 60719-83-7 (hydrochloride)
PubChem CID	2081
ChemSpider	1997 Y
UNII	C4R42570ZO
KEGG	D02787 Y
ChEMBL	ChEMBL36591 Y
CompTox Dashboard (EPA)	DTXSID5045122
Chemical and physical data
Formula	C13H18ClNO2
Molar mass	255.74 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1)CC(OC(=O)C(N)C)(C)C
InChI InChI=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 Y Key:FZSPJBYOKQPKCD-UHFFFAOYSA-N Y

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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).^[2][3]

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.^[1]

Alaproclate was first described in the scientific literature by 1978.^[1]