TFMPP

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule III DE: Anlage II (Authorized trade only, not prescriptible) NZ: Class C US: Scheduled in Florida; Unscheduled Federally II-P (Poland)[2]
Pharmacokinetic data
Metabolism	Liver CYP2D6,CYP1A2,CYP3A4
Identifiers
IUPAC name 1-[3-(trifluoromethyl)phenyl]piperazine
CAS Number	15532-75-9 N
PubChemCID	4296
ChemSpider	4145 N
UNII	25R3ONU51C
KEGG	C22745 Y
ChEBI	CHEBI:83536 N
CompTox Dashboard(EPA)	DTXSID10165876
ECHA InfoCard	100.035.962
Chemical and physical data
Formula	C11H13F3N2
Molar mass	230.234 g·mol−1
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?)  (verify)

3-Trifluoromethylphenylpiperazine (TFMPP) is arecreational drug of thephenylpiperazinechemical class and is asubstituted piperazine. Usually in combination withbenzylpiperazine (BZP) and otheranalogues, it is sold as an alternative to the illicit drugMDMA ("Ecstasy").^[4][5]

TFMPP is rarely used by itself. In fact, TFMPPreduces locomotor activity and producesaversive effects in animals rather than self-administration, which may explain the decision of the DEA not to permanently make TFMPP a controlled substance.^[6] More commonly, TFMPP is co-administered with BZP, which acts as a norepinephrine and dopamine releasing agent.^[7] Due to the serotonin agonist effects and increase in serotonin, norepinephrine, and dopamine levels produced by the BZP/TFMPP combination, this mixture of drugs produces effects which crudely mimic those ofMDMA.^[8]

In a clinical study, TFMPP produced effects in humans includingdysphoria,dextroamphetamine-like effects (i.e.,stimulant-like effects),tension andanxiety,mental confusion and "bewilderment", and increased ratings of "drug liking", "high", and "stimulated".^[9] The drug has been anecdotally reported to produce mildpsychedelic effects in humans, but nohallucinogenic effects with the drug were described in the study at the employed dose.^[9]

The combination of BZP and TFMPP has been associated with a range of side effects, includinginsomnia,anxiety,nausea and vomiting,headaches and muscle aches which may resemblemigraine,seizures,impotence, and rarelypsychosis,^[5] as well as a prolonged and unpleasanthangover effect. These side effects tend to be significantly worsened when the BZP/TFMPP mix is consumed alongsidealcohol, especially the headache, nausea, and hangover.

However, it is difficult to say how many of these side effects are produced by TFMPP itself, as it has rarely been marketed without BZP also being present, and all of the side effects mentioned are also produced by BZP (which has been sold as a single drug). Studies into other related piperazine drugs such asmCPP suggest that certain side effects such asanxiety,headache andnausea are common to all drugs of this class, and pills containing TFMPP are reported by users to produce comparatively more severe hangover effects than those containing only BZP. The drug can also cause the body to tremble for a long period of time.^{[10][unreliable source?]}

TFMPP hasaffinity for the5-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), and5-HT_2C (K_i = 62 nM)receptors, and functions as afull agonist at all sites except the 5-HT_2A receptor, where it acts as a weakpartial agonist orantagonist.^[6] Unlike the related piperazine compoundmeta-chlorophenylpiperazine (mCPP), TFMPP has insignificant affinity for the5-HT₃ receptor (IC₅₀ = 2,373 nM).^[11] TFMPP also binds to theSERT (EC₅₀ = 121 nM) and evokes therelease ofserotonin.^[6] It has no effects ondopamine ornorepinephrinereuptake or efflux.^[6]

TFMPP has been found to reduceaggression in rodents.^[12][13] It produces thehead-twitch response, a behavioral proxy ofpsychedelic effects, in rodents, and hence would be predicted to havehallucinogenic effects in humans.^[14] TFMPP was notself-administered byrhesus monkeys, suggesting that it lacksreinforcing effects.^[15]

Since 2012, TFMPP has been listed as a Schedule III controlled substance inCanada,^[16] making possession of TFMPP a federal offence. It has also been added to Part J of the Food and Drug Regulations thereby prohibiting the production, export or import of the substance.

As of October 2015 TFMPP is a controlled substance in China.^[17]

Scheduled in government decree on psychoactive substances banned from the consumer market.^[18][19][20]

As of December 3, 2005, TFMPP is illegal inDenmark.

Since 2003, TFMPP and BZP became illegal inJapan.

TFMPP is unscheduled in theNetherlands.^{[citation needed]}

Based on the recommendation of the EACD, theNew Zealand government has passed legislation which placed BZP, along with the other piperazine derivatives TFMPP, mCPP, pFPP, MeOPP and MBZP, into Class C of the New Zealand Misuse of Drugs Act 1975. A ban was intended to come into effect in New Zealand on December 18, 2007, but the law change did not go through until the following year, and the sale of BZP and the other listed piperazines became illegal in New Zealand as of 1 April 2008. An amnesty for possession and usage of these drugs remained until October 2008, at which point they became completely illegal.^[21]

As of March 1, 2006, TFMPP is scheduled as a "dangerous substance" inSweden.^[22]

As of December 1, 2010, TFMPP is a controlled substance inSwitzerland.^[23][24]

As of December 2009, TFMPP has been made a Class C drug in theUnited Kingdom along with BZP.

TFMPP is not currently scheduled at the federal level in theUnited States,^[25] but it was briefly emergency scheduled inSchedule I. The scheduling expired in April 2004 and was not renewed.^[26] However, some states such as Florida have banned the drug in their criminal statutes making its possession a felony.^[27]

TFMPP is a Schedule Icontrolled substance in the state ofFlorida making it illegal to buy, sell, or possess in Florida.^[27]

TFMPP is controlled inTexas under Penalty Group 2, as a hallucinogenic substance. It is illegal to possess TFMPP in any quantity in Texas.

• Antrafenine
• CPD-1

• Erowid: TFMPP Vault

• Drugs not assigned an ATC code
• 5-HT1A agonists
• 5-HT1B agonists
• 5-HT1D agonists
• 5-HT2A agonists
• 5-HT2C agonists
• Designer drugs
• 1-Piperazinyl compounds
• Psychedelic arylpiperazines
• Serotonin receptor agonists
• Serotonin releasing agents
• Meta-Trifluoromethylphenylpiperazines

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