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1622-79-3

1622-79-3 Structure

1622-79-3 Structure
IdentificationBack Directory
[Name]

1-[3-(p-fluorobenzoyl)propyl]-4-methylpiperazinium chloride
[CAS]

1622-79-3
[Synonyms]

Melperone HCl
Melperone-d4 HCl
MELPERONE HYDROCHLORIDE
Methylperone hydrochloride
1(4-Fluorophenol)-4-(4-methyl-1-piperidinyl)-1-butanone
1-[3-(p-fluorobenzoyl)propyl]-4-methylpiperazinium chloride
1-(4-Fluorophenyl)-4-(4-methylpiperidin-1-yl)butan-1-one HCl
1-(4-Fluorophenyl)-4-(4-methyl-1-piperidinyl)-1-butanonehydrochloride
1-(4-Fluorophenyl)-4-(4-Methylpiperidin-1-yl)butan-1-one hydrochloride
1-Butanone, 1-(4-fluorophenyl)-4-(4-methyl-1-piperidinyl)-, hydrochloride (1:1)
[EINECS(EC#)]

216-599-9
[Molecular Formula]

C15H22ClFN2O
[MDL Number]

MFCD00270922
[MOL File]

1622-79-3.mol
[Molecular Weight]

300.799
Chemical PropertiesBack Directory
[Melting point ]

209-211℃
[storage temp. ]

Desiccate at RT
[solubility ]

Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
[form ]

Solid
[color ]

White to Light Brown
[InChI]

InChI=1S/C16H22FNO.ClH/c1-13-8-11-18(12-9-13)10-2-3-16(19)14-4-6-15(17)7-5-14;/h4-7,13H,2-3,8-12H2,1H3;1H
[InChIKey]

MQHYXXIJLKFQGY-UHFFFAOYSA-N
[SMILES]

C1(=CC=C(F)C=C1)C(=O)CCCN1CCC(C)CC1.Cl
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Uses]

Melperone is a neuroleptic butyrophenone. Melperone is also an antiarrhythmic agent. Melperone is an effective atypical antipsychotic drug used in the treatment of schizophrenia.
[Biological Activity]

Atypical neuroleptic; 5-HT 2A /D 2 receptor antagonist (K i values are 120 and 180 nM respectively). Causes an increase in dopamine levels in the medial prefrontal cortex (mPFC) and nucleus accumbens and an increase in ACh in the mPFC. Also binds adrenergic α 1 and α 2 receptors (K i values are 180 and 150 nM respectively).
[Originator]

Eunerpan,Nordmark,W. Germany,1965
[Manufacturing Process]

A solution or dispersion consisting of 20.1 g (0.1 mol) of γ-chloro-pfluorobutyrophenone, 19.8 g (0.2 mol) of 4-methylpiperidine and 0.1 g of potassium iodide in 150 ml toluene is heated in a sealed glass tube for 15 hours at 100°C to 110°C. The potassium iodide and the 4-methylpiperidine hydrochloride formed in the reaction are separated by filtration and the solvent removed from the filtrate by evaporation in vacuum on a steam bath. The residue is distilled and the fraction obtained at 120°C to 125°C and at a pressure lower than 0.1 mm Hg is collected. The base is dissolved in ether and the 4-fluoro-γ-(4-methylpiperidino)-butyrophenone precipitated as the hydrochloride. The reaction product is purified by recrystallization in ethanol/ether.
Yield 22.0 g (73% of theory). MP 209°C to 211°C.
[Therapeutic Function]

Neuroleptic
Safety DataBack Directory
[Safety Profile]

Poison by ingestion, subcutaneous, and intravenous routes. Experimental teratogenic effects. A neuroleptic drug used to treat anxiety and confusion. When heated to decomposition it emits very toxic fumes of F-, NOx, and HCl.
[Toxicity]

LD50 in rats, mice (mg/kg): 330, 230 orally; 40, 35 i.v. (Christensen)
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