Alaproclate

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Alaproclate
Clinical data
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 1-(4-Chlorophenyl)-2-methylpropan-2-yl 2-aminopropanoate
JSmol)
  • Clc1ccc(cc1)CC(OC(=O)C(N)C)(C)C
  • 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 checkY
  • Key:FZSPJBYOKQPKCD-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Alaproclate (developmental code name GEA-654) is a

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.[1][2]

Synthesis

Method for Treatment of Senile Dementia:[3]

Synthesis:[4] Patent:[5] Radiolabelled:[6][7]

The

methylmagnesium iodide gives 1-(4-chlorophenyl)-2-methyl-2-propanol [5468-97-3] (2). Acylation with 2-bromopropionyl bromide [563-76-8] (3) gives [1-(4-Chlorophenyl)-2-methylpropan-2-yl] 2-bromopropanoate, CID:13695101
(3). Displacement of halogen with ammonia leads to alaproclate (4).

See also

References

  1. PMID 7996440
    .
  2. S2CID 30803162
    .
  3. ^ Ulf H. A. Lindberg, Sven-Ove gren, U.S. patent 4,469,707 (1984 to Astra Lakemedel Aktiebolag).
  4. ^ Lindberg, Ulf Henrik (1978). "Inhibitors of neuronal monoamine uptake. 2. Selective inhibition of 5-hydroxytryptamine uptake by .alpha.-amino acid esters of phenethyl alcohols". Journal of Medicinal Chemistry 21 (5): 448–456. doi:10.1021/jm00203a008.
  5. ^ Ulf M. A. Lindberg, Svante B. Ross, Seth-Olov Thorberg, Sven O. / gren, U.S. patent 4,237,311 & U.S. patent 4,331,684 (1980 & 1982 both to Astra Lakemedel Aktiebolag).
  6. ^ Gawell, Lars (1986). "Synthesis of [14C]alaproclate". Journal of Labelled Compounds and Radiopharmaceuticals. 23 (9): 947–949. doi:10.1002/jlcr.2580230905.
  7. ^ Bengtsson, Stefan; Gawell, Lars; Högberg, Thomas; Sahlberg, Christer (1985). "Synthesis and 3H NMR of 3H-alaproclate of high specific activity". Journal of Labelled Compounds and Radiopharmaceuticals. 22 (5): 427–435. doi:10.1002/jlcr.2580220503.
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