meta-Trifluoromethylphenylpiperazine (TFMPP) is a recreational drug of the phenylpiperazine chemical class and is a substituted piperazine. Usually in combination with benzylpiperazine (BZP) and other analogues, it is sold as an alternative to the illicit drug MDMA ("Ecstasy").
Use and effects
right|thumb|190px|TFMPP is off-white, yellowish in color.
TFMPP is rarely used by itself. In fact, TFMPP reduces locomotor activity and produces aversive effects in animals rather than self-administration, which may explain the decision of the DEA not to permanently make TFMPP a controlled substance. 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 of MDMA.
In clinical studies, TFMPP produced effects in humans including dysphoria, dextroamphetamine-like effects (i.e., stimulant-like effects), tension and anxiety, mental confusion and "bewilderment", and increased ratings of "drug liking", "high", and "stimulated". The drug has been anecdotally reported to produce mild psychedelic effects in humans, but no hallucinogenic effects with the drug were described in clinical studies at the employed dose.
Side effects
The combination of BZP and TFMPP has been associated with a range of side effects, including insomnia, anxiety, nausea and vomiting, headaches and muscle aches which may resemble migraine, seizures, impotence, and rarely psychosis,
Pharmacology
Pharmacodynamics
thumb|190px|right|class=skin-invert-image|4-HO-TFMPP is a metabolite of TFMPP.
TFMPP has affinity for the 5-HT<sub>1A</sub> (K<sub>i</sub> = 288–1,950 nM), 5-HT<sub>1B</sub> (K<sub>i</sub> = 30–132 nM), 5-HT<sub>1D</sub> (K<sub>i</sub> = 282 nM), 5-HT<sub>2A</sub> (K<sub>i</sub> = 160–269 nM), and 5-HT<sub>2C</sub> (K<sub>i</sub> = 62 nM) receptors, and functions as a full agonist at all sites except the 5-HT<sub>2A</sub> 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-HT<sub>3</sub> receptor (IC<sub>50</sub> = 2,373 nM). TFMPP also binds to the SERT (EC<sub>50</sub> = 121 nM) and evokes the release of serotonin. In one study, TFMPP did not produce the head-twitch response on its own, but when combined with the selective serotonin 5-HT<sub>2C</sub> receptor antagonist SB-242084, it was able to dose-dependently induce head twitches. TFMPP was not self-administered by rhesus monkeys, suggesting that it lacks reinforcing effects.
Pharmacokinetics
The pharmacokinetics of TFMPP have been studied.
Chemistry
Synthesis
The chemical synthesis of TFMPP has been described.
Derivatives
- Antrafenine
- CPD-1
History
TFMPP was first described in the scientific literature in 1978.
Society and culture
Legal status
Canada
Since 2012, TFMPP has been listed as a Schedule III controlled substance in Canada, 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.
China
As of October 2015 TFMPP is a controlled substance in China.
Denmark
As of December 3, 2005, TFMPP is illegal in Denmark.
Finland
Scheduled in government decree on psychoactive substances banned from the consumer market.
Japan
Since 2003, TFMPP and BZP became illegal in Japan.
Netherlands
TFMPP is unscheduled in the Netherlands.
New Zealand
Based on the recommendation of the EACD, the New 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.
Sweden
As of March 1, 2006, TFMPP is scheduled as a "dangerous substance" in Sweden.
Switzerland
As of December 1, 2010, TFMPP is a controlled substance in Switzerland.
United Kingdom
As of December 2009, TFMPP has been made a Class C drug in the United Kingdom along with BZP.
United States
TFMPP is not currently scheduled at the federal level in the United States, but it was briefly emergency scheduled in Schedule I. The scheduling expired in April 2004 and was not renewed. However, some states such as Florida have banned the drug in their criminal statutes making its possession a felony.
Florida
TFMPP is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.