Chlorproethazine

Chlorproethazine
Names

IUPAC name 3-(2-chlorophenothiazin-10-yl)-N,N-diethylpropan-1-amine
Identifiers
CAS Number	84-01-5^Y 4611-02-3^N
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL2105938^N
ChemSpider	59173^N
ECHA InfoCard	100.001.373
KEGG	D07308^Y
PubChem	65750 65750
UNII	960NX27Z07^Y
InChI InChI=1S/C19H23ClN2S/c1-3-21(4-2)12-7-13-22-16-8-5-6-9-18(16)23-19-11-10-15(20)14-17(19)22/h5-6,8-11,14H,3-4,7,12-13H2,1-2H3^N Key: DBOUGBAQLIXZLV-UHFFFAOYSA-N^N InChI=1/C19H23ClN2S/c1-3-21(4-2)12-7-13-22-16-8-5-6-9-18(16)23-19-11-10-15(20)14-17(19)22/h5-6,8-11,14H,3-4,7,12-13H2,1-2H3 Key: DBOUGBAQLIXZLV-UHFFFAOYAP
SMILES Clc2cc1N(c3c(Sc1cc2)cccc3)CCCN(CC)CC
Properties
Chemical formula	C₁₉H₂₃ClN₂S
Molar mass	346.91732 g/mol
Pharmacology
ATC code	N05AA07 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Chlorproethazine is an antipsychotic.

Synthesis

Chlorproethazine can be synthesized from a diphenylsulfide derivative. The general scheme is sufficiently flexible to permit the interchange of the order of some of the steps.

Thus alkylation of aniline thioether () with 3-chloro-1-diethylaminopropane leads to the intermediate (). Ring closure as above by nucleophilic aromatic displacement leads to the antipsychotic drug chlorproethazine.^[1]

References

↑ Buisson, P.; Gailliot, P.; 1956, U.S. Patent 2,769,002

Antipsychotics (neuroleptics) (N05A)

Typical	Benzamides Levosulpiride Sulpiride Veralipride^‡ Butyrophenones Azaperone Benperidol Bromperidol Droperidol Fluanisone Haloperidol^# Lenperone Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines Clopimozide Fluspirilene Penfluridol Pimozide Phenothiazines Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine) Chloracizine Chlorproethazine Chlorpromazine Cyamemazine Dixyrazine Fluacizine Fluphenazine Levomepromazine/Methotrimeprazine Mesoridazine Perazine Periciazine Perphenazine Perphenazine 4-aminobutyrate Piperacetazine Pipotiazine Prochlorperazine Promazine Promethazine Sulforidazine Thiethylperazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes Chlorprothixene Clopenthixol Clothixamide Flupentixol Fluprothixene Piflutixol Teflutixol Thiothixene Zuclopenthixol Tricyclics Fluotracen Loxapine Trimipramine Others Butaclamol Prothipendyl

Atypical	Benzamides Amisulpride Nemonapride Remoxipride^‡ Sultopride Tiapride Butyrophenones Cinuperone Melperone Setoperone Benzo(iso)oxazole piperidines Iloperidone Ocaperidone^§ Paliperidone Risperidone^# Benzo(iso)thiazole piperazines Lurasidone Perospirone Revospirone^§ Tiospirone^§ Ziprasidone Diphenylbutylpiperazines Amperozide Phenylpiperazines Aripiprazole Aripiprazole lauroxil Bifeprunox^§ Brexpiprazole Cariprazine Tricyclics Amoxapine Asenapine Carpipramine Clocapramine Clorotepine Clotiapine Clozapine^# Flumezapine Fluperlapine Gevotroline Metitepine Mosapramine Olanzapine Quetiapine Tenilapine Zotepine Others Blonanserin Lumateperone^† Molindone Pimavanserin RP5063^† Sertindole Zicronapine^§

Others	Azacyclonol Cannabidiol Oxypertine Reserpine Tetrabenazine

^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

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