THC Science

Perazine
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	N05AB10 (WHO) ;
Identifiers
	IUPAC name 10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine;
CAS Number	84-97-9 ;
PubChem CID	4744;
DrugBank	DB12710 ;
ChemSpider	4582 ;
UNII	8915147A2B;
KEGG	C16903;
ChEBI	CHEBI:59118 ;
ChEMBL	ChEMBL1697766;
CompTox Dashboard (EPA)	DTXSID6048628 ;
ECHA InfoCard	100.001.435
Chemical and physical data
Formula	C20H25N3S
Molar mass	339.50 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=CC=CC=C42;
	InChI InChI=1S/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3 ; Key:WEYVCQFUGFRXOM-UHFFFAOYSA-N ;
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Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. It is quite similar to chlorpromazine, and acts as a dopamine antagonist. A 2014 systematic review compared it with other antipsychotic drugs:

Perazine versus other antipsychotic drugs for schizophrenia^[1]

Summary

The number, size and reporting of randomized controlled perazine trials are insufficient to present firm conclusions about the properties of this antipsychotic. It is possible that perazine is associated with a similar risk of extrapyramidal side effects as some atypical antipsychotics but this is based on few comparisons of limited power.^[1]

Outcome	Findings in words	Findings in numbers	Quality of evidence
Global state
No better or deterioration Follow-up: average 5 weeks	Perazine may decrease the chance of experiencing this outcome. These findings are based on data of low quality.	RR 0.43 (0.23 to 0.81)	Low
Mental state
Less than 30% BPRS reduction Follow-up: mean 5 weeks	The average overall mental state score in the perazine group was lower than for those given other antipsychotic drugs but the difference between the groups was not clear. These findings are based on data of low quality.	RR 0.82 (0.61 to 1.09)	Low
Adverse effects
Needing antiparkinson medication Follow-up: average 5 weeks	Perazine might increase the risk of experiencing this outcome but at present it is not possible to be confident about the difference between perazine and other antipsychotic drugs. Data supporting this finding are very limited.	RR 4.5 (1.04 to 19.45)	Very low
Leaving the study early - due to adverse events Follow-up: average 4 weeks	There was not a clear difference between perazine and the other antipsychotic drugs for this general outcome reflecting overall adverse event 'load'. These findings are based on data of low quality.	0.87 (0.4 to 1.9)	Low
Acceptability of treatment
Leaving the studies early - any reason Follow-up: 5 weeks	Perazine and the comparison antipsychotic drugs were equally tolerated. These findings are based on data of low quality.	RR 0.62 (0.35 to 1.1)	Low
	No study reported any data on outcomes such as quality of life or information relating to satisfaction with care.

Synthesis[edit]

Phenothiazine-10-propionitrile [1698-80-2] (1) is treated with a mixture of acid and alcohol giving Methyl phenothiazinepropionate, CID:368244 (2). Heating with 1-methylpiperazine (3) gives the amide [91508-47-3] (4). Reduction of this last by means of diborane yields Perazine (5).

References[edit]

^ ^a ^b Leucht S, Helfer B, Hartung B (January 2014). "Perazine for schizophrenia". The Cochrane Database of Systematic Reviews. 1 (1): CD002832. doi:10.1002/14651858.CD002832.pub3. PMC 11015532. PMID 24425538.
^ Hromatka, O.; Sauter, F.; Schlager, L. H. (1957). "Untersuchungen über Phenthiazinderivate III: Über die Synthese von 10-(Piperazinoalkyl)-phenthiazinen". Monatshefte für Chemie. 88 (2): 193–201. doi:10.1007/BF00901625.
^ Hromatka, O.; Stehlik, G.; Sauter, F. (1960). "Untersuchungen über Phenthiazinderivate, 12. Mitt.: Reaktionen zur Géwinnung von 10-(?-Methylpiperazinylpropyl)-phenthiazin". Monatshefte für Chemie 91 (1): 107–116. doi:10.1007/BF00903173.
^ GB780193 idem Horclois Raymond Jacques, U.S. patent 2,902,485 (1957 to Rhône-Poulenc).
^ Anon., GB 901187 (1962 to Chemische Fabrik Promonta GmbH).
^ Owen, Terence C. (1984). "Synthesis of perazine". Journal of Heterocyclic Chemistry. 21 (1): 265–266. doi:10.1002/jhet.5570210154.
^ Brufani; Cesta; Filocamo; Lappa; Marta; Pomponi; Meroni; Pagella Farmaco, 1992, vol. 47, # 5 p. 585 – 597.

External links[edit]

Perazine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

[Leu2014-1] Leucht S, Helfer B, Hartung B (January 2014). "Perazine for schizophrenia". The Cochrane Database of Systematic Reviews. 1 (1): CD002832. doi:10.1002/14651858.CD002832.pub3. PMC 11015532. PMID 24425538.

[2] Hromatka, O.; Sauter, F.; Schlager, L. H. (1957). "Untersuchungen über Phenthiazinderivate III: Über die Synthese von 10-(Piperazinoalkyl)-phenthiazinen". Monatshefte für Chemie. 88 (2): 193–201. doi:10.1007/BF00901625.

[3] Hromatka, O.; Stehlik, G.; Sauter, F. (1960). "Untersuchungen über Phenthiazinderivate, 12. Mitt.: Reaktionen zur Géwinnung von 10-(?-Methylpiperazinylpropyl)-phenthiazin". Monatshefte für Chemie 91 (1): 107–116. doi:10.1007/BF00903173.

[4] GB780193 idem Horclois Raymond Jacques, U.S. patent 2,902,485 (1957 to Rhône-Poulenc).

[5] Anon., GB 901187 (1962 to Chemische Fabrik Promonta GmbH).

[6] Owen, Terence C. (1984). "Synthesis of perazine". Journal of Heterocyclic Chemistry. 21 (1): 265–266. doi:10.1002/jhet.5570210154.

[7] Brufani; Cesta; Filocamo; Lappa; Marta; Pomponi; Meroni; Pagella Farmaco, 1992, vol. 47, # 5 p. 585 – 597.

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Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Others/unknown: Azacyclonol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (Tricyclic antidepressants (TCAs))	Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Batelapine Butriptyline Cianopramine Ciclazindol Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) (desmethylimipramine) Desmethylclomipramine Desmethyltrimipramine Dibenzepin Dimetacrine Dosulepin (dothiepin) Doxepin Enprazepine Fantridone Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mirtazapine Monometacrine Nitroxazepine Norbutriptyline Nordoxepin Northiaden (nordosulepin) Nortriptyline (noramitriptyline) Noxiptiline Octriptyline Opipramol Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene Promethazine Propiomazine Rupatadine Thiazinamium
Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Citatepine Clocapramine Clomacran Clorotepine Clotiapine Clozapine Cyanothepin Doclothepin Docloxythepin Erizepine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Isofloxythepin Levomepromazine/Methotrimeprazine Loxapine Lurasidone Maroxepin Meperathiepin Mesoridazine Metiapine Metitepine Metoxepin Mosapramine Naranol Octomethothepin Olanzapine Oxyclothepin Oxyprothepin Pentiapine Peradithiepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Savoxepin/Cipazoxapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Tilozepine Traboxopine Trifluoperazine Triflupromazine Trifluthepin Zotepine Zuclopenthixol
Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline Rispenzepine
Anticholinergics	Profenamine Tropatepine
Others	Adosopine Aminopromazine Atiprosin Beloxepin Benzoctamine Carvedilol Cidoxepin Cyclobenzaprine Damotepine Darenzepine Elanzepine Fluradoline Methylene blue Monatepil Nuvenzepine Oxetorone Perlapine Pipazethate P7C3 Pinadoline Pirenzepine Pirolate Pitrazepin Pizotifen Serazapine Siltenzepine Telenzepine Tipindole Zolenzepine

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