U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08908
Gene ID: 3350.0
Gene Symbol: HTR1A
Target Organism: Homo sapiens (Human)
288.0 nM [Ki]
Target ID: P28222
Gene ID: 3351.0
Gene Symbol: HTR1B
Target Organism: Homo sapiens (Human)
132.0 nM [Ki]
Target ID: P28221
Gene ID: 3352.0
Gene Symbol: HTR1D
Target Organism: Homo sapiens (Human)
282.0 nM [Ki]
Target ID: P28223
Gene ID: 3356.0
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
269.0 nM [Ki]
Target ID: P28335
Gene ID: 3358.0
Gene Symbol: HTR2C
Target Organism: Homo sapiens (Human)
62.0 nM [Ki]
Target ID: P31645
Gene ID: 6532.0
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
121.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy').
2005 Mar
The clinical toxicology of the designer "party pills" benzylpiperazine and trifluoromethylphenylpiperazine.
2011 Mar
Patents

Sample Use Guides

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
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:58:40 UTC 2023
Edited
by admin
on Fri Dec 15 17:58:40 UTC 2023
Record UNII
25R3ONU51C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-(3-TRIFLUOROMETHYLPHENYL)PIPERAZINE
Systematic Name English
TFMPP
Common Name English
NSC-128882
Code English
TFTP
Common Name English
3-TRIFLUOROMETHYLPHENYLPIPERAZINE
Systematic Name English
PIPERAZINE, 1-(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)-
Systematic Name English
FLIBANSERIN METABOLITE M30A
Common Name English
J209.034A
Code English
PIPERAZINE, 1-(3-(TRIFLUOROMETHYL)PHENYL)-
Systematic Name English
N-(ALPHA,ALPHA,ALPHA-TRIFLUORO-3-TOLYL)PIPERAZINE
Systematic Name English
TRIFLUOROMETHYLPHENYLPIPERAZINE
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA Designer-drugs-Trifluoromethylphenylpiperazine
Created by admin on Fri Dec 15 17:58:40 UTC 2023 , Edited by admin on Fri Dec 15 17:58:40 UTC 2023
Code System Code Type Description
CHEBI
83536
Created by admin on Fri Dec 15 17:58:40 UTC 2023 , Edited by admin on Fri Dec 15 17:58:40 UTC 2023
PRIMARY
EPA CompTox
DTXSID10165876
Created by admin on Fri Dec 15 17:58:40 UTC 2023 , Edited by admin on Fri Dec 15 17:58:40 UTC 2023
PRIMARY
CAS
15532-75-9
Created by admin on Fri Dec 15 17:58:40 UTC 2023 , Edited by admin on Fri Dec 15 17:58:40 UTC 2023
PRIMARY
ECHA (EC/EINECS)
239-574-4
Created by admin on Fri Dec 15 17:58:40 UTC 2023 , Edited by admin on Fri Dec 15 17:58:40 UTC 2023
PRIMARY
NSC
128882
Created by admin on Fri Dec 15 17:58:40 UTC 2023 , Edited by admin on Fri Dec 15 17:58:40 UTC 2023
PRIMARY
PUBCHEM
4296
Created by admin on Fri Dec 15 17:58:40 UTC 2023 , Edited by admin on Fri Dec 15 17:58:40 UTC 2023
PRIMARY
WIKIPEDIA
TRIFLUOROMETHYLPHENYLPIPERAZINE
Created by admin on Fri Dec 15 17:58:40 UTC 2023 , Edited by admin on Fri Dec 15 17:58:40 UTC 2023
PRIMARY
MESH
C018406
Created by admin on Fri Dec 15 17:58:40 UTC 2023 , Edited by admin on Fri Dec 15 17:58:40 UTC 2023
PRIMARY
FDA UNII
25R3ONU51C
Created by admin on Fri Dec 15 17:58:40 UTC 2023 , Edited by admin on Fri Dec 15 17:58:40 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
MAJOR
URINE
Related Record Type Details
ACTIVE MOIETY