Zipeprol

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Zipeprol

Systematic (IUPAC) name
1-methoxy- 3-[4-(2-methoxy- 2-phenylethyl)piperazin- 1-yl]- 1-phenylpropan- 2-ol
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	Schedule I (US) Schedule II international
Routes	Oral
Identifiers
CAS number	34758-83-3
ATC code	R05DB15
PubChem	CID 36910
ChemSpider	33868^Y
UNII	G5MUV8139H^Y
KEGG	D07390^Y
Chemical data
Formula	C₂₃H₃₂N₂O₃
Mol. mass	384.512 g/mol
SMILES	eMolecules & PubChem
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
Y(what is this?) (verify)

Zipeprol is a centrally acting cough suppressant developed in France in the 1970s.^[1] 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]

[edit] 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. edit
^ 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. edit

Opioids

Opium and
poppy straw
derivatives

Crude opiate extracts/
whole opium products

Compote/Kompot/Polish heroin • Diascordium • B & O Supprettes • Dover's powder • Kendal Black Drop • Laudanum • Mithridate • Opium • Paregoric • Poppy straw concentrate • Poppy tea • Smoking opium • Theriac

Natural opiates

Opium alkaloids see also: Components of opium	Codeine • Morphine • Oripavine • Pseudomorphine • Thebaine

Alkaloid salts mixtures	Pantopon • Papaveretum (Omnopon)

Semisynthetics
including
Bentley compounds

Morphine family	2,4-Dinitrophenylmorphine • 6-Methylenedihydrodesoxymorphine • Chlornaltrexamine • Dihydrodesoxymorphine (Desomorphine) • Dihydromorphine • Hydromorphinol • Methyldesorphine • N-Phenethylnormorphine • RAM-378

3,6-diesters of morphine	Acetylpropionylmorphine • Diacetyldihydromorphine (Dihydroheroin, Acetylmorphinol) • Dibenzoylmorphine • Dipropanoylmorphine • Heroin (Diacetylmorphine) • Nicomorphine

Codeine-dionine family	6-Monoacetylcodeine • Benzylmorphine • Codeine methylbromide • Methyldihydromorphine (Dihydroheterocodeine) • Ethylmorphine (Dionine) • Heterocodeine • Morpholinylethylmorphine (Pholcodine) • Myrophine

Morphinones and morphols	14-Cinnamoyloxycodeinone • 14-Ethoxymetopon • 14-Methoxymetopon • 14-Phenylpropoxymetopon • 7-Spiroindanyloxymorphone • Acetylmorphone • Codeinone • Codorphone • Codoxime • Thebacon (Acetyldihydrocodeinone / Dihydrocodeinone enol acetate) • Hydrocodone • Hydromorphone • Metopon • Morphinone • N-Phenethyl-14-ethoxymetopon • Oxycodone • Oxymorphol • Oxymorphone • Pentamorphone • Semorphone

Morphides	Chloromorphide

Dihydrocodeine series	14-hydroxydihydrocodeine • Acetyldihydrocodeine • Dihydrocodeine • Nicocodeine • Nicodicodeine

Nitrogen morphine derivatives	Morphine-N-Oxide

Hydrazones	Oxymorphazone

Halogenated morphine derivatives	1-Iodomorphine

Active opiate
metabolites

Morphine-6-glucuronide • 6-Monoacetylmorphine • Norcodeine • Normorphine

Morphinans

Morphinan series	Cyclorphan • Dextrallorphan • Levorphanol • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Methorphan / Racemethorphan • Morphanol / Racemorphanol • Ro4-1539 • Xorphanol

Others	Butorphanol • Cyprodime • Drotebanol • Nalbuphine • Sinomenine (Cocculine)

Benzomorphans

8-Carboxamidocyclazocine • Alazocine • Bremazocine • Dezocine • Ketazocine • Metazocine • Pentazocine • Phenazocine

4-Phenylpiperidines

Pethidines (Meperidines)	4-Fluoromeperidine • Allylnorpethidine • Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Morpheridine • Oxpheneridine (Carbamethidine) • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine

Prodines	Allylprodine • Meprodine (α-meprodine / β-meprodine) • MPPP (Desmethylprodine) • PEPAP • Prodine (α-prodine / β-prodine) • Prosidol • Trimeperidine (Promedol)

Ketobemidones	Acetoxyketobemidone • Droxypropine • Ketobemidone • Methylketobemidone • Propylketobemidone

Others	Alvimopan • Loperamide • Picenadol

Open chain
opioids

Amidones	Dipipanone • Methadone • Normethadone • Phenadoxone (Heptazone)

Methadols	Dimepheptanol (Racemethadol) • Levacetylmethadol

Moramides	Dextromoramide • Levomoramide • Racemoramide

Thiambutenes	Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene • Piperidylthiambutene • Pyrrolidinylthiambutene • Thiambutene • Tipepidine

Phenalkoxams	Dextropropoxyphene (Propoxyphene) • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Norpropoxyphene

Ampromides	Diampromide • Phenampromide • Propiram

Others	IC-26 • Isoaminile • Lefetamine • R-4066

Anilidopiperidines

3-Allylfentanyl • 3-Methylfentanyl • 3-Methylthiofentanyl • 4-Phenylfentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • β-methylfentanyl • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Mirfentanil • Ocfentanil • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thiofentanyl • Trefentanil

Oripavine
derivatives

7-PET • Acetorphine • BU-48 • Buprenorphine • Cyprenorphine • Dihydroetorphine • Etorphine • Homprenorphine • Norbuprenorphine

Phenazepanes

Ethoheptazine • Meptazinol • Metheptazine • Metethoheptazine • Proheptazine

Pirinitramides

Bezitramide • Piritramide

Benzimidazoles

Clonitazene • Etonitazene

Indoles

18-MC • 7-Hydroxymitragynine • Akuammine • Eseroline • Hodgkinsine • Mitragynine • Pericine

Diphenylmethylpiperazines

BW373U86 • DPI-221 • DPI-287 • DPI-3290 • SNC-80

Opioid peptides
see also: Opioid neuropeptides

Adrenorphin • Amidorphin • Casomorphin • Cytochrophin • DADLE • DAMGO • Deltorphin • Dermenkephalin • Dermorphin • Dynorphin • Endomorphin • Endorphin • Enkephalin • Gliadorphin • Hemorphin • Leumorphin • Morphiceptin • Neoendorphin • Nociceptin • Octreotide • Opiorphin • Rimorphin • Rubiscolin • Spinorphin • TRIMU 5 • Tynorphin • Valorphin

Others

AD-1211 • AH-7921 • Azaprocin • BDPC • BRL-52537 • Bromadoline • C-8813 • Ciramadol • Doxpicomine • Enadoline • Faxeladol • GR-89696 • Herkinorin • ICI-199,441 • ICI-204,448 • J-113,397 • JTC-801 • Ketamine • LPK-26 • Methopholine • MT-45 • N-Desmethylclozapine • NNC 63-0532 • Nortilidine • O-Desmethyltramadol • Phencyclidine • Prodilidine • Profadol • Ro64-6198 • Salvinorin A • SB-612,111 • SC-17599 • RWJ-394,674 • TAN-67 • Tapentadol • Tifluadom • Tilidine • Tramadol • Trimebutine • U-50,488 • U-69,593 • Viminol • W-18

Opioid antagonists
&
inverse agonists

5'-Guanidinonaltrindole • Alvimopan • Chlornaltrexamine • Cyclazocine • Cyprodime • Diprenorphine (M5050) • JDTic • Levallorphan • Methylnaltrexone • Nalfurafine • Nalmefene • Naloxazone • Naloxonazine • Naloxone • Nalorphine • Naltrexol-d4 • Naltrexone • Naltriben • Naltrindole • Norbinaltorphimine • Oxilorphan

List of opioids

Cough and cold preparations (R05)

Expectorants

Althea root • Antimony pentasulfide • Creosote • Guaiacolsulfonate • Guaifenesin • Ipecacuanha (Syrup of ipecac) • Levoverbenone • Potassium iodide • Senega • Tyloxapol

Mucolytics

Acetylcysteine • Ambroxol • Bromhexine • Carbocisteine • Domiodol • Dornase alfa • Eprazinone • Erdosteine • Letosteine • Mesna • Neltenexine • Sobrerol • Stepronin • Tiopronin

Cough suppressants

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

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

M: RES

anat(n, x, l, c)/phys/devp

noco(c, p)/cong/tumr, sysi/epon, injr

proc, drug(R1/2/3/5/6/7)

v · d · ePiperazines

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 • Naphthylpiperazine • Nefazodone • Niaprazine • Oxypertine • Pardoprunox • pCPP • pFPP • Posaconazole • PRX-00023 • 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 • WAY-100,135 • WAY-100,635

Benzylpiperazines	2C-B-BZP • Befuraline • Bifeprunox • Buclizine • BZP • Chlorbenzoxamine • DBZP • Fipexide • Imatinib • MBZP • MDBZP • Meclozine • Piberaline • Piribedil • 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 • 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	6-Nitroquipazine • Azimilide • Cinepazet • Cyclohexylpiperazine • Hexocyclium • Indinavir • JNJ-7777120 • Lodenafil • Mirodenafil • PB-28 • Quipazine • Ranolazine • SA-4503 • Sildenafil • Tadalafil • Vardenafil • VUF-6002 • Zipeprol

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Zipeprol

[edit] References

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