TFMPP HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H13F3N2.ClH
Molecular Weight	266.69
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=DGNLGWJZZZOYPT-UHFFFAOYSA-N

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

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15496938 | https://www.ncbi.nlm.nih.gov/pubmed/20924753 | https://www.ncbi.nlm.nih.gov/pubmed/27358233

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 Target ID: P08908 Gene ID: 3350.0 Gene Symbol: HTR1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15496938	Agonist 2678	288.0 nM [Ki]
5-hydroxytryptamine receptor 1B 21 Target ID: P28222 Gene ID: 3351.0 Gene Symbol: HTR1B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15496938	Agonist 2678	132.0 nM [Ki]
5-hydroxytryptamine receptor 1D 17 Target ID: P28221 Gene ID: 3352.0 Gene Symbol: HTR1D Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15496938	Agonist 2678	282.0 nM [Ki]
5-hydroxytryptamine receptor 2A 69 Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15496938	Partial Agonist 290	269.0 nM [Ki]
5-hydroxytryptamine receptor 2C 26 Target ID: P28335 Gene ID: 3358.0 Gene Symbol: HTR2C Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15496938	Agonist 2678	62.0 nM [Ki]
Sodium-dependent serotonin transporter 40 Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15496938	Activator 1430	121.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy').	2005 Mar	15496938
The clinical toxicology of the designer "party pills" benzylpiperazine and trifluoromethylphenylpiperazine.	2011 Mar	21495881

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).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:14:16 GMT 2023` Edited by `admin` on `Sat Dec 16 11:14:16 GMT 2023`
Record UNII	41P8ENH29V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TFMPP HYDROCHLORIDE

Common Name

English

1-(3-(TRIFLUOROMETHYL)PHENYL)PIPERAZINIUM CHLORIDE

Systematic Name

English

PIPERAZINE, 1-(3-(TRIFLUOROMETHYL)PHENYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

1-(3-TRIFLUOROMETHYLPHENYL)PIPERAZINE HYDROCHLORIDE

Systematic Name

English

PIPERAZINE, 1-(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)-, MONOHYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID10166808