Trifluoromethylphenylpiperazine

Trifluoromethylphenylpiperazine
Clinical data


Routes of administration	Oral
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule III DE: Anlage II (Prohibited) Unscheduled in US. Class C drug in New Zealand , II-P(Poland)
Identifiers
IUPAC name 1-[3-(trifluoromethyl)phenyl]piperazine
CAS Number	15532-75-9^N
PubChem (CID)	4296
ChemSpider	4145^N
ChEBI	CHEBI:83536^N
ECHA InfoCard	100.035.962
Chemical and physical data
Formula	C₁₁H₁₃F₃N₂
Molar mass	230.23 g/mol
InChI InChI=1S/C11H13F3N2/c12-11(13,14)9-3-1-2-4-10(9)16-7-5-15-6-8-16/h1-4,15H,5-8H2^Y Key:VZUBMIDXJRGARE-UHFFFAOYSA-N^Y
^NY (what is this?)

3-Trifluoromethylphenylpiperazine (TFMPP) is a recreational drug of the piperazine chemical class. Usually in combination with its analogue benzylpiperazine (BZP), it is sold as an alternative to the illicit drug MDMA ("Ecstasy") under the name "Legal X".

TFMPP has affinity for the 5-HT_1A (K_i = 288 nM), 5-HT_1B (K_i = 132 nM), 5-HT_1D (K_i = 282 nM), 5-HT_2A (K_i = 269 nM), and 5-HT_2C (K_i = 62 nM) receptors, and functions as a full agonist at all sites except the 5-HT_2A receptor, where it acts as a weak partial agonist or antagonist. Unlike the related piperazine compound meta-chlorophenylpiperazine (mCPP), TFMPP has insignificant affinity for the 5-HT₃ receptor (IC₅₀ = 2,373 nM). TFMPP also binds to the SERT (EC₅₀ = 121 nM) and evokes the release of serotonin. It has no effects on dopamine or norepinephrine reuptake or efflux.