Zipeprol

Zipeprol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	R05DB15 (WHO) ;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule III; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I; UN: Psychotropic Schedule II;
Identifiers
	IUPAC name 1-methoxy- 3-[4-(2-methoxy- 2-phenylethyl)piperazin- 1-yl]- 1-phenylpropan- 2-ol;
CAS Number	34758-83-3 ;
PubChem CID	36910;
ChemSpider	33868 ;
UNII	G5MUV8139H;
KEGG	D07390 ;
CompTox Dashboard (EPA)	DTXSID00865732 ;
ECHA InfoCard	100.047.432
Chemical and physical data
Formula	C23H32N2O3
Molar mass	384.520 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC(CN1CCN(CC1)CC(OC)c2ccccc2)C(OC)c3ccccc3;
	InChI InChI=1S/C23H32N2O3/c1-27-22(19-9-5-3-6-10-19)18-25-15-13-24(14-16-25)17-21(26)23(28-2)20-11-7-4-8-12-20/h3-12,21-23,26H,13-18H2,1-2H3 ; Key:VSTNNAYSCJQCQI-UHFFFAOYSA-N ;
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Zipeprol is a centrally acting cough suppressant developed in France in the 1970s.^[2] It is not a morphinan derivative (in contrast to codeine and dextromethorphan). Zipeprol acts as a local anaesthetic and has mucolytic, antihistamine and anticholinergic properties.^[3] It is sold with several brand names such as Zinolta and Respilene. It is not available in the United States or Canada and has been discontinued in Europe. It is still available in some countries in Asia and South America.

Zipeprol has been misused in Korea, mainly for the hallucinations it produces. Such use has become an issue due to the seizures and various neurological side effects it causes at high dosages.^[4]

References

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ Patent US 3718650, Mauvernay RY, "New Derivatives of Substituted Piperazines", issued 1973-02-27
^ Rispat G, Burgi H, Cosnier D, Duchêne-Marullaz P, Streichenberger G (April 1976). "General pharmacological properties of a new non-opiate antitussive: zipeprol (3024 CERM). I. Action on respiratory function and acute toxicity". Arzneimittel-Forschung. 26 (4): 523–30. PMID 8057.
^ Chung H, Park M, Hahn E, Choi H, Choi H, Lim M (October 2004). "Recent trends of drug abuse and drug-associated deaths in Korea". Annals of the New York Academy of Sciences. 1025 (1): 458–64. Bibcode:2004NYASA1025..458C. doi:10.1196/annals.1316.056. PMID 15542749. S2CID 10987790.

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[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[2] Patent US 3718650, Mauvernay RY, "New Derivatives of Substituted Piperazines", issued 1973-02-27

[3] Rispat G, Burgi H, Cosnier D, Duchêne-Marullaz P, Streichenberger G (April 1976). "General pharmacological properties of a new non-opiate antitussive: zipeprol (3024 CERM). I. Action on respiratory function and acute toxicity". Arzneimittel-Forschung. 26 (4): 523–30. PMID 8057.

[4] Chung H, Park M, Hahn E, Choi H, Choi H, Lim M (October 2004). "Recent trends of drug abuse and drug-associated deaths in Korea". Annals of the New York Academy of Sciences. 1025 (1): 458–64. Bibcode:2004NYASA1025..458C. doi:10.1196/annals.1316.056. PMID 15542749. S2CID 10987790.

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v t e Piperazines
Simple piperazines (no additional rings)	Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	2C-B-PP 3,4-CFP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine JJC8-088 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol