1-(3-TRIFLUOROMETHYLPHENYL)PIPERAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H13F3N2
Molecular Weight	230.2295
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 1-(3-TRIFLUOROMETHYLPHENYL)PIPERAZINE

SMILES

FC(F)(F)C1=CC=CC(=C1)N2CCNCC2

InChI

InChIKey=KKIMDKMETPPURN-UHFFFAOYSA-N

InChI=1S/C11H13F3N2/c12-11(13,14)9-2-1-3-10(8-9)16-6-4-15-5-7-16/h1-3,8,15H,4-7H2

HIDE SMILES / InChI

Molecular Formula	C11H13F3N2
Molecular Weight	230.2295
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Trifluoromethylphenylpiperazine (TFMPP) acts on serotonin receptors 5-HT1A, 5-HT1B, 5-HT1D, 5-HT2A and 5-HT2C and functions as a full agonist at all sites except the 5-HT2A receptor, where it acts as a weak partial agonist or antagonist. In addition, TFMPP binds to the sodium-dependent serotonin transporter, SERT and evokes the release of serotonin. Besides was shown, that the N-Benzylpiperazine/TFMPP combination produced effects, which crudely mimic those of MDMA, commonly known as ecstasy. The neurophysiological effects of TFMPP in humans was also studied and was shown that TFMPP may affect transmitter systems involved in speeding of interhemispheric communication in the male brain.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
5-hydroxytryptamine receptor 1A 54	Agonist 2,678	288.0 nM [Ki]
5-hydroxytryptamine receptor 1B 21	Agonist 2,678	132.0 nM [Ki]
5-hydroxytryptamine receptor 1D 17	Agonist 2,678	282.0 nM [Ki]
5-hydroxytryptamine receptor 2A 69	Partial Agonist 290	269.0 nM [Ki]
5-hydroxytryptamine receptor 2C 26	Agonist 2,678	62.0 nM [Ki]
Sodium-dependent serotonin transporter 40	Activator 1,430	121.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2,578

PubMed

Title	Date	PubMed
No data available in table

Patents

Sample Use Guides

In Vivo Use Guide

Healthy, right-handed males (age: 25 ± 5.6 years) were given placebo (n = 15) or TFMPP (0.94 mg/kg, oral, n = 15) and tested both pre- and 2 h post-drug administration

Route of Administration: Oral

In Vitro Use Guide

It was investigated the cytotoxic effects of mixtures of N-Benzylpiperazine (BZP) and 1-(3-trifluoromethylphenyl)piperazine (TFMPP) in vitro. Human-derived HepaRG cells and primary rat hepatocytes were exposed to the drugs, individually or combined at different mixture ratios, and cytotoxicity was assessed by the MTT assay. It was observed that primary rat hepatocytes are more sensitive than HepaRG cells to the toxicity of BZP (EC50 2.20 and 6.60 mM, respectively) and TFMPP (EC50 0.14 and 0.45 mM, respectively). For all BZP-TFMPP combinations tested, CA was the most appropriate model to predict the mixture effects. TFMPP proved to act additively with BZP to produce significant hepatotoxicity (p < 0.01).