Aceprometazine

Aceprometazine
Clinical data
Pregnancy; category	Contraindicated; Passes into breast milk;
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal and fecal
Identifiers
	IUPAC name 1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethanone;
CAS Number	13461-01-3 ;
PubChem CID	26035;
DrugBank	DB01615 ;
ChemSpider	24249 ;
UNII	984N9YTM4Y;
ChEBI	CHEBI:53770 ;
ChEMBL	ChEMBL2104054;
CompTox Dashboard (EPA)	DTXSID00864407 ;
ECHA InfoCard	100.033.315
Chemical and physical data
Formula	C19H22N2OS
Molar mass	326.46 g·mol−1
3D model (JSmol)	Interactive image;
	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.^[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 are on account of a methadone-type aziridine.

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

References

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

[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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