Tolpiprazole

Tolpiprazole
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 1-(3-Methylphenyl)-4-[2-(5-methyl-1H-pyrazol-3-yl)ethyl]piperazine;
CAS Number	20326-13-0;
PubChem CID	3084338;
ChemSpider	2341419;
UNII	8XP74P4HO3;
CompTox Dashboard (EPA)	DTXSID90174224 ;
Chemical and physical data
Formula	C17H24N4
Molar mass	284.407 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cc3cccc(N2CCN(CCc1cc(C)[nH]n1)CC2)c3;

Tolpiprazole (INN, BAN) (developmental code name H-4170) is an anxiolytic drug of the phenylpiperazine group that was never marketed.^[1]

Synthesis

The last step in the synthesis involves attachement of the sidechain of 3-(2-chloroethyl)-5-methyl-pyrazole [54055-29-7] (1) with 1-m-tolylpiperazine [41186-03-2] (2) giving Tolpiprazole (3).

References

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1217–. ISBN 978-1-4757-2085-3.
^ Anon., NL 7317477 (1975 to Merck Patent Gmbh)
^ Volker Koppe, et al. U.S. patent 3,491,097 (1970 to Merck KGaA).

[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1217–. ISBN 978-1-4757-2085-3.

[2] Anon., NL 7317477 (1975 to Merck Patent Gmbh)

[3] Volker Koppe, et al. U.S. patent 3,491,097 (1970 to Merck KGaA).

[1]

[2]

[3]

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 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone 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

Synthesis

See also

References