Zipeprol

Zipeprol
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	R05DB15 (WHO)
Legal status
Legal status	CA: Schedule III DE: Anlage II (Prohibited) US: Schedule I Schedule II international
Identifiers
IUPAC name 1-methoxy- 3-[4-(2-methoxy- 2-phenylethyl)piperazin- 1-yl]- 1-phenylpropan- 2-ol
CAS Number	34758-83-3^N
PubChem (CID)	36910
ChemSpider	33868^Y
UNII	G5MUV8139H^Y
KEGG	D07390^Y
ECHA InfoCard	100.047.432
Chemical and physical data
Formula	C₂₃H₃₂N₂O₃
Molar mass	384.512 g/mol
3D model (Jmol)	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^Y Key:VSTNNAYSCJQCQI-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Zipeprol is a centrally acting cough suppressant developed in France in the 1970s.^[1] It is not an morphinan derivative (in contrast to codeine and dextromethorphan). Zipeprol acts as a local anaesthetic and has mucolytic, antihistamine and anticholinergic properties.^[2]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.^[3]

References

↑ 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. (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): 523–530. PMID 8057.
↑ Chung, H.; Park, M.; Hahn, E.; Choi, H.; Choi, H.; Lim, M. (2004). "Recent Trends of Drug Abuse and Drug-Associated Deaths in Korea". Annals of the New York Academy of Sciences. 1025: 458–464. doi:10.1196/annals.1316.056. PMID 15542749.

Cough and cold preparations (R05)

Expectorants

Mucolytics

Cough suppressants

Opium alkaloids, opioids, and derivatives	Acetyldihydrocodeine Benzylmorphine Butorphanol Codeine Dextromethorphan Dihydrocodeine Dimemorfan Droxypropine Ethylmorphine Heroin Hydrocodone Hydromorphone Isoaminile Laudanum Levomethadone Levopropoxyphene Methadone Nicocodeine Nicodicodeine Normethadone Noscapine Pholcodine Thebacon Tipepidine

Other	Benzonatate Benproperine Bibenzonium bromide Butamirate Clobutinol Clofedanol Cloperastine Diphenhydramine Dibunate Dimethoxanate Dropropizine Fedrilate Glaucine Levodropropizine Meprotixol Morclofone Nepinalone Oxolamine Oxeladin Pentoxyverine Pipazetate Prenoxdiazine Piperidione Zipeprol

Piperazines

Simple piperazines (no additional rings)	1-Cyclohexylpiperazine Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES

Phenylpiperazines	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 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 Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide Piberaline Piribedil Sunifiram Trimetazidine Vesnarinone

Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine Lidoflazine Manidipine Meclozine Oxatomide SNC-80 Vanoxerine

Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone

Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine 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 Azimilide Cinepazet Cinepazic acid Cinepazide Cyclohexylpiperazine Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 Zipeprol

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