Aceprometazine

Chemical compound
  • Contraindicated
    Passes into breast milk
Routes of
administrationOralATC code
  • none
Legal statusLegal status
  • In general: ℞ (Prescription only)
Pharmacokinetic dataMetabolismHepaticExcretionRenal and fecalIdentifiers
  • 1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethanone
CAS Number
  • 13461-01-3 checkY
PubChem CID
  • 26035
DrugBank
  • DB01615 checkY
ChemSpider
  • 24249 checkY
UNII
  • 984N9YTM4Y
ChEBI
  • CHEBI:53770 checkY
ChEMBL
  • ChEMBL2104054
ECHA InfoCard100.033.315 Edit this at WikidataChemical and physical dataFormulaC19H22N2OSMolar mass326.46 g·mol−13D model (JSmol)
  • Interactive image
  • O=C(c2cc1N(c3c(Sc1cc2)cccc3)CC(N(C)C)C)C
  • InChI=1S/C19H22N2OS/c1-13(20(3)4)12-21-16-7-5-6-8-18(16)23-19-10-9-15(14(2)22)11-17(19)21/h5-11,13H,12H2,1-4H3 checkY
  • Key:XLOQNFNTQIRSOX-UHFFFAOYSA-N checkY
  (verify)

Aceprometazine (INN) is a phenothiazine derivative prescription drug with neuroleptic and anti-histamine properties It is not widely prescribed, and may be associated with drug-induced Parkinsonism.[1] It may be used in combination with meprobamate for the treatment of sleep disorders. This combination is available in France under the trade name Mepronizine.

It is structurally related to the phenothiazine derivative veterinary drug acepromazine.

Synthesis

Note: The reason for the rearrangement in the sidechain between the precursor and the product is on account of a methadone-type aziridine.

Patent Ex 6:[2]

2-Acetylphenothiazine [6631-94-3] (1) 2-Chloropropyldimethylamine [108-14-5] (2)

References

  1. ^ Blanchet PJ, Kivenko V (2016-09-23). "Drug-induced parkinsonism: diagnosis and management". Journal of Parkinsonism and Restless Legs Syndrome: 83–91. doi:10.2147/JPRLS.S99197. hdl:1866/19491.
  2. ^ Martin L Kantor & Tubis Samuel, U.S. patent 3,100,772 (1963 to Wyeth LLC).


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  • See also: Receptor/signaling modulators
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  • Monoamine reuptake inhibitors
  • Monoamine releasing agents
  • Monoamine metabolism modulators
  • Monoamine neurotoxins


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