Trifluoromethylphenylpiperazine

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Trifluoromethylphenylpiperazine
Systematic (IUPAC) name
1-(3-(Trifluoromethyl)phenyl)piperazine
Identifiers
CAS number 15532-75-9
ATC code ?
PubChem 4296
Chemical data
Formula C11H13F3N2 
Mol. mass 230.23 g/mol
Pharmacokinetic data
Bioavailability ?
Metabolism hepatic
Half life ?
Excretion renal
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes oral

3-Trifluoromethylphenylpiperazine (or simply TFMPP) is a piperazine-based drug. It has no medical uses, but has been sold as a recreational drug used as a "legal alternative" to illicit drugs such as LSD and MDMA.


Pharmacology and Effects

TFMPP acts as a non-selective agonist at 5-HT1B,[1] 5-HT2A and 5-HT2C serotonin receptors. TFMPP is rarely administered by itself, and there has been little research into it as a single drug. More commonly, TFMPP is co-administered with another piperazine derivative BZP, which increases synaptic levels of serotonin and dopamine via action at the VMAT-2 vesicular monoamine transporter,[2] in addition to being a serotonin agonist in its own right.

Due to the serotonin agonist effects and increase in dopamine levels produced by the BZP/TFMPP combination, this mixture of drugs produces effects which crudely mimic the effects of MDMA ("ecstasy") in animals,[3] and so have been advertised as an "MDMA substitute" to consumers.[4] The subjective effects of this combination are often portrayed as being similar to those of MDMA, but actually are quite different, lacking any empathogenic effects.

In fact the effects of TFMPP are more similar to hallucinogens such as LSD or (more similarly) mescaline, although much weaker, with the maximal 5-HT2A agonist effect of TFMPP found to be only 40% compared to the strong hallucinogen DOM.[5] So it would be more accurate to describe the combination of BZP and TFMPP as being closer to a combination of a weak dose of LSD mixed with amphetamine rather than comparing it to MDMA.

However research has shown that in addition to the effects on serotonin, the combination results in an unexpectedly large amount of dopamine release that far exceeds what one would expect from the DA releasing properties of each drug alone added together. This suggests a strong degree of synergy between the two drugs. [1]

TFMPP has only mild effects when not combined with benzylpiperazine, and it produces aversive effects in animals rather than self-administration, which explains the decision not to permanently make TFMPP an illicit drug.

TFMPP has also been previously reported as a metabolite of the analgesic antrafenine.[6] TFMPP shares some features with fenfluramine.

The dosage commonly used when combined with BZP for "ecstasy-like effects" is between 30 and 100 mg, while higher doses of TFMPP alone cause mildly hallucinogenic effects at around 100–250mg; however, higher doses can cause a range of side effects including migraine headaches, muscle aches, nausea and vomiting, as well as a come-down syndrome characterised by insomnia, loss of appetite, and headache; these side effects tend to discourage abuse of TFMPP.

Legal Status

File:TFMPP.jpg
TFMPP is off-white, yellowish in color.

As of December 3rd 2005, TFMPP is illegal in Denmark. As of March 1 2006, TFMPP is scheduled as a "dangerous substance" in Sweden.[7] TFMPP was briefly emergency scheduled in Schedule I in the USA, but the scheduling expired in April 2004 and has not been renewed.[8] Therefore, unlike its cousin benzylpiperazine, TFMPP is not currently an illicit drug in the USA.

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, as well as a prolonged and unpleasant hangover effect similar to that produced by alcohol. These side effects tend to be significantly worsened when the BZP/TFMPP mix is consumed alongside alcohol, 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 as mCPP suggest that certain side effects such as anxiety, headache and nausea 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. [9]

See also

External links

Footnotes

  1. Schechter MD (1988): "Use of TFMPP stimulus properties as a model of 5-HT1B receptor activation." Pharmacol.Biochem.Behav. 31(1), 53-7. PMID 3252260
  2. Partilla JS, Dempsey AG, Nagpal AS, Blough BE, Baumann MH, Rothman RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. Journal of Pharmacology and Experimental Therapeutics. 2006 Oct;319(1):237-46.
  3. Yarosh HL, Katz EB, Coop A, Fantegrossi WE. MDMA-like behavioral effects of N-substituted piperazines in the mouse. Pharmacology, Biochemistry and Behavior. 2007 Nov;88(1):18-27.
  4. erowid
  5. Glennon RA, McKenney JD, Young R. (1984): "Discriminative stimulus properties of the serotonin agonist 1-(3-trifluoromethylphenyl)piperazine (TFMPP)". Life Sciences. 35(14):1475-80. PMID 6482668
  6. Caccia S, Conti I, Notarnicola A. (1985): "In-vivo metabolism in the rat and mouse of antrafenine to 1-m-trifluoromethylphenylpiperazine." Journal of Pharmacy and Pharmacology. 37(1):75-7. PMID 2858538
  7. http://www.erowid.org/chemicals/tfmpp/tfmpp_law.shtml
  8. U.S. Department of Justice, Drug Enforcement Administration (DEA), Scheduling Actions 2002
  9. Wilkins C, Girling M, Sweetsur P, Huckle T, Huakau J. "Legal party pill use in New Zealand: Prevalence of use, availability, health harms and ‘gateway effects’ of benzylpiperazine (BZP) and triflourophenylmethylpiperazine (TFMPP)" (PDF). Centre for Social and Health Outcomes Research and Evaluation (SHORE). Retrieved 2007-04-14. 

de:TFMPP


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