Aceprometazine

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.

Not to be confused with Acepromazine.
Aceprometazine
Clinical data
Pregnancy
category
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal and fecal
Identifiers
IUPAC name
  • 1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethanone
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard100.033.315
Chemical and physical data
FormulaC19H22N2OS
Molar mass326.46 g·mol−1
3D model (JSmol)
SMILES
  • O=C(c2cc1N(c3c(Sc1cc2)cccc3)CC(N(C)C)C)C
InChI
  • 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 Y
  • Key:XLOQNFNTQIRSOX-UHFFFAOYSA-N Y
  (verify)

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.
  2. Martin L Kantor & Tubis Samuel, U.S. Patent 3,100,772 (1963 to Wyeth LLC).



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