The effect of niaprazine on the turnover of 5-hydroxytryptamine in the rat brain

Keane, P.E.; Benedetti, Μ. Strolin; J, Dow

doi:10.1016/0028-3908(82)90157-5

Cited by 18 publications

(5 citation statements)

References 22 publications

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“…Previous studies have indicated the importance of cytochrome P450 (CYP) isozymes CYP2D6, CYP1A2 and CYP3A4 in the metabolism of TFMPP, 4 and preliminary data on the inhibitory effects of BZP and TFMPP on these enzymes have already been reported 5 . Several studies have also described the metabolism of MeOPP, 6 MDBP, 7 mCPP 8,9 and pFPP, 10 again implicating major P450 enzymes in the hydroxylation and/or de‐methylation of these drugs.…”

Section: Introductionmentioning

confidence: 98%

Metabolic interactions with piperazine-based ‘party pill’ drugs

Antia

Tingle

Russell

2009

Journal of Pharmacy and Pharmacology

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Fluorophenylpiperazine, methoxyphenylpiperazine, chlorophenylpiperazine, methylbenzylpiperazine and methylenedioxybenzylpiperazine had significant inhibitory effects on CYP2D6, CYP1A2, CYP3A4, CYP2C19 and CYP2C9 isoenzymes but each piperazine had a different inhibitory profile. The metabolic interaction between BZP and TFMPP may have clinical implications, as these agents are often combined in 'party pills'.

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Section: Introductionmentioning

confidence: 98%

Metabolic interactions with piperazine-based ‘party pill’ drugs

Antia

Tingle

Russell

2009

Journal of Pharmacy and Pharmacology

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“…1) leads to the cleavage of the side chain to yield p-fluorophenylpiperazine (pFPP). Interestingly, unlike parent niaprazine, pFPP shows no sedative properties and instead produces a behavioral syndrome indicative for serotonergic stimulation [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some Aminophosphonates Bearing N‐(Fluorophenyl)‐piperazynyl Moiety and Their Activity toward Serotonin Receptors

Lewkowski

Jóźwiak

Tokarz

et al. 2015

Heteroatom Chemistry

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“…N-(4-fluorophenyl)piperazine (C 10 H 13 N 2 F; 4-FPP) has mild psychedelic and euphorigenic properties and, in this respect, it exhibits effects similar to those of the related compound N-(4methoxyphenyl)piperazine (MeOPP), which has been used as a recreational drug (Nagai et al, 2007). 4-FPP is also is a major metabolite (Keane et al, 1982;Sanjuan et al, 1983) of the sedative and hypnotic drug niaprazine, N-{4-[4-(4-fluorophenyl)piperazin-1-yl]butan-2-yl}pyridine-3-carboxamide, used in the treatment of autistic disorders (Rossi et al, 1999).…”

Section: Chemical Contextmentioning

confidence: 99%

The crystal structures of salts of N-(4-fluorophenyl)piperazine with four aromatic carboxylic acids and with picric acid

Chinthal

Yathirajan

Kavitha³

et al. 2020

Acta Cryst E

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The structures are reported for five salts formed by reactions between N-(4-fluorophenyl)piperazine and aromatic acids. In 4-(4-fluorophenyl)piperazin-1-ium 2-fluorobenzoate monohydrate, C10H14FN2 +·C7H4FO2 −·H2O, (I), the components are linked by a combination of N—H...O and O—H...O hydrogen bonds to form a chain of alternating R 4 6(12) and R 6 6(16) rings. The ionic components of 4-(4-fluorophenyl)piperazin-1-ium 2-bromobenzoate 0.353-hydrate, C10H14FN2 +·C7H4BrO2 −·0.353H2O, (II), are linked by N—H...O hydrogen bonds to form a centrosymmetric four-ion aggregate containing an R 4 4(12) motif, and these aggregates are linked into a molecular ladder by a single C—H...π(arene) hydrogen bond. 4-(4-Fluorophenyl)piperazin-1-ium 2-iodobenzoate, C10H14FN2 +·C7H4IO2 −, (III), crystallizes with Z′ = 2 in space group P\overline{1}: the four independent ions are linked by N—H...O hydrogen bonds to form a non-centrosymmetric aggregate again containing an R 4 4(12) motif, and aggregates of this type are linked into a ribbon by a combination of C—H...O and C—H...π(arene) hydrogen bonds. The anion in 4-(4-fluorophenyl)piperazin-1-ium 2,4,6-trinitrophenolate, C10H14FN2 +·C6H2N3O7 −, (IV), shows clear evidence of extensive electronic delocalization from the phenolate O atom into the adjacent ring. The ions are linked by a combination of two-centre N—H...O and three-centre N—H...(O)2 hydrogen bonds to form centrosymmetric four-ion aggregates containing three types of ring. The ions in 4-(4-fluorophenyl)piperazin-1-ium 3,5-dinitrobenzoate, C10H14FN2 +·C7H3N2O6 −, (V), are again linked by N—H...O hydrogen bonds to form centrosymmetric R 4 4(12) aggregates, which are themselves linked by a C—H...π(arene) hydrogen bond to form sheets, the stacking of which leads to the formation of narrow channels, containing disordered and/or mobile solvent entities. Comparisons are made with some related structures.

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The effect of niaprazine on the turnover of 5-hydroxytryptamine in the rat brain

Cited by 18 publications

References 22 publications

Metabolic interactions with piperazine-based ‘party pill’ drugs

Metabolic interactions with piperazine-based ‘party pill’ drugs

Synthesis of Some Aminophosphonates Bearing N‐(Fluorophenyl)‐piperazynyl Moiety and Their Activity toward Serotonin Receptors

The crystal structures of salts of N-(4-fluorophenyl)piperazine with four aromatic carboxylic acids and with picric acid

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