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Amperozide

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Amperozide
Clinical data
ATCvet code
Identifiers
  • 4-[4,4-bis(4-fluorophenyl)butyl]-N-ethylpiperazine-1-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H29F2N3O
Molar mass401.502 g·mol−1
3D model (JSmol)
  • CCNC(=O)N1CCN(CC1)CCCC(C2=CC=C(C=C2)F)C3=CC=C(C=C3)F
  • 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) checkY
  • Key:NNAIYOXJNVGUOM-UHFFFAOYSA-N checkY
  (verify)

Amperozide is an atypical antipsychotic of the diphenylbutylpiperazine class which acts as an antagonist at the 5-HT2A 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]

Synthesis

According to Arvid Carlsson, behavioural Stimulation in rat:[10]

Patents:[11][12]

The reaction of ethylisocyanate [109-90-0] (1) with N-benzylpiperazine (2) leads to the corresponding urea, CID:47103368 (3). Catalytic hydrogenation cleaves the benzyl protecting group giving N-ethylpiperazine-1-carboxamide [75529-72-5] (4). Alkylation of the unmasked nitrogen with 1,1'-(4-Chlorobutylidene)Bis(4-Fluorobenzene) [3312-04-7] (5) completed the synthesis of amperozide (6).

References

  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.
  10. ^ Waters N, Pettersson G, Carlsson A, Svensson K (August 1989). "The putatively antipsychotic agent amperozide produces behavioural stimulation in the rat: A behavioural and biochemical characterization". Naunyn-Schmiedeberg's Archives of Pharmacology. 340 (2): 161–169. doi:10.1007/BF00168964. PMID 2572972. S2CID 6673216. Retrieved 22 October 2022.
  11. ^ DE2941880 idem Anders K. K. Bjork, Knut G. Olsson, Aina L. Abramo, Erik G. Christensson, U.S. patent 4,447,433 (1984 to Ab Ferrosan).
  12. ^ Anders K. K. Bjork, Knut G. Olsson, Aina L. Abramo, Erik G. Christensson, U.S. patent 4,385,057 (1983 to Ab Ferrosan).
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