Chemistry:Amperozide

Amperozide
Clinical data
ATCvet code	QN05AX90 (WHO) ;
Identifiers
	IUPAC name 4-[4,4-bis(4-fluorophenyl)butyl]-N-ethylpiperazine-1-carboxamide;
CAS Number	75558-90-6 ;
PubChem CID	73333;
ChemSpider	66062 ;
UNII	0M2W3TAG39;
ChEMBL	ChEMBL1079935 ;
Chemical and physical data
Formula	C23H29F2N3O
Molar mass	401.502 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCNC(=O)N1CCN(CC1)CCCC(C2=CC=C(C=C2)F)C3=CC=C(C=C3)F;
	InChI InChI=1S/C23H29F2N3O/c1-2-26-23(29)28-16-14-27(15-17-28)13-3-4-22(18-5-9-20(24)10-6-18)19-7-11-21(25)12-8-19/h5-12,22H,2-4,13-17H2,1H3,(H,26,29) ; Key:NNAIYOXJNVGUOM-UHFFFAOYSA-N ;
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Short description: Chemical compound

Amperozide is an atypical antipsychotic of the diphenylbutylpiperazine class which acts as an antagonist at the 5-HT_2A receptor.^[1] It does not block dopamine receptors as with most antipsychotic drugs,^[2] but does inhibit dopamine release,^[3]^[4] and alters the firing pattern of dopaminergic neurons.^[5] It was investigated for the treatment of schizophrenia in humans,^[6] but never adopted clinically. Its main use is instead in veterinary medicine, primarily in intensively farmed pigs, for decreasing aggression and stress and thereby increasing feeding and productivity.^[7]^[8]^[9]

References

↑ "Receptor binding properties of amperozide". Pharmacology & Toxicology 66 (Suppl 1): 8–11. 1990. doi:10.1111/j.1600-0773.1990.tb01599.x. PMID 2154737.
↑ "Effect of amperozide on rat cortical 5-HT2 and striatal and limbic dopamine D2 receptor occupancy: implications for antipsychotic action". European Journal of Pharmacology 216 (1): 67–71. May 1992. doi:10.1016/0014-2999(92)90210-u. PMID 1388121.
↑ "Amperozide, a putative anti-psychotic drug: uptake inhibition and release of dopamine in vitro in the rat brain". Life Sciences 47 (23): 2111–7. 1990. doi:10.1016/0024-3205(90)90310-n. PMID 1979998.
↑ "The effect of the atypical antipsychotic drug, amperozide, on carrier-mediated striatal dopamine release measured in vivo". The Journal of Pharmacology and Experimental Therapeutics 263 (1): 180–5. October 1992. PMID 1403783.
↑ "Effects of amperozide, a putative antipsychotic drug, on rat midbrain dopamine neurons recorded in vivo". Pharmacology & Toxicology 66 (Suppl 1): 29–33. 1990. doi:10.1111/j.1600-0773.1990.tb01603.x. PMID 2304893.
↑ "Effects of amperozide in schizophrenia. An open study of a potent 5-HT2 receptor antagonist". Psychopharmacology 104 (3): 287–92. 1991. doi:10.1007/bf02246025. PMID 1924636.
↑ "Thin sow syndrome (TSS): the effect of amperozide". The British Veterinary Journal 146 (5): 463–7. 1990. doi:10.1016/0007-1935(90)90036-3. PMID 2224491.
↑ "Observations on the action of amperozide: are there social influences on sow-litter productivity?". Research in Veterinary Science 51 (2): 169–73. September 1991. doi:10.1016/0034-5288(91)90008-C. PMID 1788479.
↑ "[Practical experiences in the therapy of postweaning edema disease in piglets]". Berliner und Munchener Tierarztliche Wochenschrift 109 (10): 385–7. October 1996. PMID 8999770.

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[1] "Receptor binding properties of amperozide". Pharmacology & Toxicology 66 (Suppl 1): 8–11. 1990. doi:10.1111/j.1600-0773.1990.tb01599.x. PMID 2154737.

[2] "Effect of amperozide on rat cortical 5-HT2 and striatal and limbic dopamine D2 receptor occupancy: implications for antipsychotic action". European Journal of Pharmacology 216 (1): 67–71. May 1992. doi:10.1016/0014-2999(92)90210-u. PMID 1388121.

[3] "Amperozide, a putative anti-psychotic drug: uptake inhibition and release of dopamine in vitro in the rat brain". Life Sciences 47 (23): 2111–7. 1990. doi:10.1016/0024-3205(90)90310-n. PMID 1979998.

[4] "The effect of the atypical antipsychotic drug, amperozide, on carrier-mediated striatal dopamine release measured in vivo". The Journal of Pharmacology and Experimental Therapeutics 263 (1): 180–5. October 1992. PMID 1403783.

[5] "Effects of amperozide, a putative antipsychotic drug, on rat midbrain dopamine neurons recorded in vivo". Pharmacology & Toxicology 66 (Suppl 1): 29–33. 1990. doi:10.1111/j.1600-0773.1990.tb01603.x. PMID 2304893.

[6] "Effects of amperozide in schizophrenia. An open study of a potent 5-HT2 receptor antagonist". Psychopharmacology 104 (3): 287–92. 1991. doi:10.1007/bf02246025. PMID 1924636.

[7] "Thin sow syndrome (TSS): the effect of amperozide". The British Veterinary Journal 146 (5): 463–7. 1990. doi:10.1016/0007-1935(90)90036-3. PMID 2224491.

[8] "Observations on the action of amperozide: are there social influences on sow-litter productivity?". Research in Veterinary Science 51 (2): 169–73. September 1991. doi:10.1016/0034-5288(91)90008-C. PMID 1788479.

[9] "[Practical experiences in the therapy of postweaning edema disease in piglets]". Berliner und Munchener Tierarztliche Wochenschrift 109 (10): 385–7. October 1996. PMID 8999770.

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v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Droperidol Haloperidol^# Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine Piperacetazine Pipotiazine Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Flupentixol Tiotixene (thiothixene) Zuclopenthixol
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine 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 Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Azacyclonol Cannabidiol Oxypertine Reserpine Tetrabenazine
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e 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 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 Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide Piberaline Piribedil 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 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 EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

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Clinical data

ATCvet code	QN05AX90 (WHO)
Identifiers
IUPAC name 4-[4,4-bis(4-fluorophenyl)butyl]-N-ethylpiperazine-1-carboxamide
CAS Number	75558-90-6^Y
PubChem CID	73333
ChemSpider	66062^Y
UNII	0M2W3TAG39
ChEMBL	ChEMBL1079935^Y
Chemical and physical data
Formula	C₂₃H₂₉F₂N₃O
Molar mass	401.502 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCNC(=O)N1CCN(CC1)CCCC(C2=CC=C(C=C2)F)C3=CC=C(C=C3)F
InChI InChI=1S/C23H29F2N3O/c1-2-26-23(29)28-16-14-27(15-17-28)13-3-4-22(18-5-9-20(24)10-6-18)19-7-11-21(25)12-8-19/h5-12,22H,2-4,13-17H2,1H3,(H,26,29)^Y Key:NNAIYOXJNVGUOM-UHFFFAOYSA-N^Y
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