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Aceprometazine

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Chemical compound Not to be confused with Acepromazine.
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Pharmaceutical compound
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--10H-phenothiazin-2-yl}ethanone
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.033.315 Edit this at Wikidata
Chemical and physical data
FormulaC19H22N2OS
Molar mass326.46 g·mol
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
  • Key:XLOQNFNTQIRSOX-UHFFFAOYSA-N
  (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. 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-Acetylphenothiazine (1) 2-Chloropropyldimethylamine (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).


Dopamine receptor modulators
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists


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