Amperozide

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]

ATCvet code

QN05AX90 (WHO)

CAS Number

75558-90-6^Y

PubChem CID

73333

ChemSpider

66062^Y

Quick facts Clinical data, ATCvet code ...

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^Y
PubChem CID	73333
ChemSpider	66062^Y
UNII	0M2W3TAG39
ChEMBL	ChEMBL1079935^Y
CompTox Dashboard (EPA)	DTXSID6048416
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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[1]
Svartengren J, Simonsson P (1990). "Receptor binding properties of amperozide". Pharmacology & Toxicology. 66 (Suppl 1): 8–11. doi:10.1111/j.1600-0773.1990.tb01599.x. PMID 2154737.
[2]
Meltzer HY, Zhang Y, Stockmeier CA (May 1992). "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. doi:10.1016/0014-2999(92)90210-u. PMID 1388121.
[3]
Eriksson E (1990). "Amperozide, a putative anti-psychotic drug: uptake inhibition and release of dopamine in vitro in the rat brain". Life Sciences. 47 (23): 2111–7. doi:10.1016/0024-3205(90)90310-n. PMID 1979998.
[4]
Yamamoto BK, Meltzer HY (October 1992). "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. PMID 1403783.
[5]
Grenhoff J, Tung CS, Ugedo L, Svensson TH (1990). "Effects of amperozide, a putative antipsychotic drug, on rat midbrain dopamine neurons recorded in vivo". Pharmacology & Toxicology. 66 (Suppl 1): 29–33. doi:10.1111/j.1600-0773.1990.tb01603.x. PMID 2304893.
[6]
Axelsson R, Nilsson A, Christensson E, Björk A (1991). "Effects of amperozide in schizophrenia. An open study of a potent 5-HT2 receptor antagonist". Psychopharmacology. 104 (3): 287–92. doi:10.1007/bf02246025. PMID 1924636. S2CID 2507927.
[7]
Kyriakis SC, Martinsson K, Olsson NG, Bjork A (1990). "Thin sow syndrome (TSS): the effect of amperozide". The British Veterinary Journal. 146 (5): 463–7. doi:10.1016/0007-1935(90)90036-3. PMID 2224491.
[8]
Kyriakis SC, Olsson NG, Martinsson K, Björk AK (September 1991). "Observations on the action of amperozide: are there social influences on sow-litter productivity?". Research in Veterinary Science. 51 (2): 169–73. doi:10.1016/0034-5288(91)90008-C. PMID 1788479.
[9]
Papp I, Waller C, Biro O (October 1996). "[Practical experiences in the therapy of postweaning edema disease in piglets]". Berliner und Munchener Tierarztliche Wochenschrift. 109 (10): 385–7. PMID 8999770.

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