Trifluoromethylphenylpiperazine

Last updated
Trifluoromethylphenylpiperazine
TFMPP.svg
TFMPP-3D-vdW.png
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
  • 1-[3-(trifluoromethyl)phenyl]piperazine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard 100.035.962 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H13F3N2
Molar mass 230.234 g·mol−1
  • 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 Yes check.svgY
  • Key:VZUBMIDXJRGARE-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)
4-HO-TFMPP is a metabolite of TFMPP. HO-TFMPP.png
4-HO-TFMPP is a metabolite of TFMPP.
TFMPP is off-white, yellowish in color. TFMPP.jpg
TFMPP is off-white, yellowish in color.

3-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"). [4] [5]

Contents

Pharmacology

TFMPP has affinity for the 5-HT1A (Ki = 288 nM), 5-HT1B (Ki = 132 nM), 5-HT1D (Ki = 282 nM), 5-HT2A (Ki = 269 nM), and 5-HT2C (Ki = 62 nM) receptors, and functions as a full agonist at all sites except the 5-HT2A receptor, where it acts as a weak partial agonist or antagonist. [6] Unlike the related piperazine compound meta-chlorophenylpiperazine (mCPP), TFMPP has insignificant affinity for the 5-HT3 receptor (IC50 = 2,373 nM). [7] TFMPP also binds to the SERT (EC50 = 121 nM) and evokes the release of serotonin. [6] It has no effects on dopamine or norepinephrine reuptake or efflux. [6]

Use and effects

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. [6] More commonly, TFMPP is co-administered with BZP, which acts as a norepinephrine and dopamine releasing agent. [8] 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. [9]

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, [5] as well as a prolonged and unpleasant hangover effect. 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. The drug can also cause the body to tremble for a long period of time. [10] [ unreliable source? ]

Canada

Since 2012, TFMPP has been listed as a Schedule III controlled substance in Canada, [11] 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. [12]

Finland

Scheduled in government decree on psychoactive substances banned from the consumer market. [13] [14] [15]

Denmark

As of December 3, 2005, TFMPP is illegal in Denmark.

Japan

Since 2003, TFMPP and BZP became illegal in Japan.

Netherlands

TFMPP is unscheduled in the Netherlands. [ citation needed ]

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. [16]

Sweden

As of March 1, 2006, TFMPP is scheduled as a "dangerous substance" in Sweden. [17]

Switzerland

As of December 1, 2010, TFMPP is a controlled substance in Switzerland. [18] [19]

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, [20] but it was briefly emergency scheduled in Schedule I. The scheduling expired in April 2004 and was not renewed. [21] However, some states such as Florida have banned the drug in their criminal statutes making its possession a felony. [22]

Florida

TFMPP is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida. [22]

Texas

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

Derivatives

Related Research Articles

<span class="mw-page-title-main">2C-D</span> Chemical compound

2C-D is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity was subsequently investigated in humans by Alexander Shulgin. In his book PiHKAL, Shulgin lists the dosage range as being from 20 to 60 mg. Lower doses of 10 mg or less have been explored for microdosing.

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine (MDA), sometimes referred to as “sass,” is an empathogen-entactogen, stimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

<i>para</i>-Methoxyamphetamine Chemical compound

para-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogen effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.

<span class="mw-page-title-main">4-HO-DiPT</span> Chemical compound

4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.

<span class="mw-page-title-main">Benzylpiperazine</span> Recreational drug

Benzylpiperazine (BZP) is a substance often used as a recreational drug and is known to have euphoriant and stimulant properties. Several studies conducted between 2000 and 2011 found that the effects of BZP are similar to amphetamine, although BZP's dosage is roughly 10 times higher by weight.

<span class="mw-page-title-main">Piperazine</span> Chemical compound

Piperazine is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste.

<span class="mw-page-title-main">5-MeO-MiPT</span> Chemical compound

5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

<span class="mw-page-title-main">Butylone</span> Entactogen, psychedelic, and stimulant drug of the phenethylamine class

Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine chemical class. It is the β-keto analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.

<span class="mw-page-title-main">AL-LAD</span> Chemical compound (psychedelic drug)

AL-LAD, also known as 6-allyl-6-nor-LSD, is a psychedelic drug and an analog of lysergic acid diethylamide (LSD). It is described by Alexander Shulgin in the book TiHKAL. It is synthesized starting from nor-LSD as a precursor, using allyl bromide as a reactant.

<i>meta</i>-Chlorophenylpiperazine Stimulant

meta-Chlorophenylpiperazine (mCPP) is a psychoactive drug of the phenylpiperazine class. It was initially developed in the late-1970s and used in scientific research before being sold as a designer drug in the mid-2000s. It has been detected in pills touted as legal alternatives to illicit stimulants in New Zealand and pills sold as "ecstasy" in Europe and the United States.

<i>para</i>-Methoxyphenylpiperazine Chemical compound

para-Methoxyphenylpiperazine is a piperazine derivative with stimulant effects which has been sold as an ingredient in "Party pills", initially in New Zealand and subsequently in other countries around the world.

<i>para</i>-Fluorophenylpiperazine Chemical compound

para-Fluorophenylpiperazine is a piperazine derivative with mildly psychedelic and euphoriant effects. It has been sold as an ingredient in legal recreational drugs known as "Party pills", initially in New Zealand and subsequently in other countries around the world.

<span class="mw-page-title-main">Methylbenzylpiperazine</span> Chemical compound

Methylbenzylpiperazine is a stimulant drug which is a derivative of benzylpiperazine. MBZP has been sold as an ingredient in legal recreational drugs known as "party pills", initially in New Zealand and subsequently in other countries around the world.

<span class="mw-page-title-main">2C-B-BZP</span> Chemical compound

4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP) is a psychoactive drug and research chemical of the piperazine chemical class which has been sold as a "designer drug". It produces stimulant effects similar to those of benzylpiperazine (BZP).

<span class="mw-page-title-main">6-APB</span> Psychoactive drug

6-APB is an empathogenic psychoactive drug of the substituted benzofuran and substituted phenethylamine classes. 6-APB and other compounds are sometimes informally called "Benzofury" in newspaper reports. It is similar in structure to MDA, but differs in that the 3,4-methylenedioxyphenyl ring system has been replaced with a benzofuran ring. 6-APB is also the unsaturated benzofuran derivative of 6-APDB. It may appear as a tan grainy powder.

<span class="mw-page-title-main">5-MAPB</span> Chemical compound

5-MAPB is an entactogenic designer drug similar to MDMA in its structure and effects.

<span class="mw-page-title-main">1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine</span> Chemical compound

1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine (3C-PEP) is a designer drug of the piperazine class of chemical substances. 3C-PEP is related to meta-cholorophenylpiperazine (mCPP) and phenethylamine that can be thought of as mCPP having a phenylethyl group attached to the nitrogen atom at its 4-position. It was first described in 1994 in a patent disclosing a series of piperazine compounds as sigma receptor ligands. Later, it was discovered to be a highly potent dopamine reuptake inhibitor.

Substituted piperazines are a class of chemical compounds based on a piperazine core. Some are used as recreational drugs and some are used in scientific research.

<i>ortho</i>-Methylphenylpiperazine Chemical compound

ortho-Methylphenylpiperazine (also known as oMPP, oMePP, 1-(2-methylphenyl)piperazine, 2-MPP, and 2-MePP) is a psychoactive designer drug of the phenylpiperazine group. It acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50 values for induction of monoamine release of 175 nM for serotonin, 39.1 nM for norepinephrine, and 296–542 nM for dopamine. As such, it has about 4.5-fold preference for induction of norepinephrine release over serotonin, and about 7.6- to 13.9-fold preference for induction of norepinephrine release over dopamine.

<span class="mw-page-title-main">CUMYL-CBMINACA</span> Chemical compound

CUMYL-CBMINACA (SGT-277) is an indazole-3-carboxamide based synthetic cannabinoid receptor agonist that has been sold as a designer drug, first being identified in Germany in February 2020. It is illegal in Finland.

References

  1. Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 17 June 2011.
  3. "4-(Piperazin-1-yl)-2-(trifluoromethyl)phenol".
  4. "Erowid TFMPP Vault: Basics". Erowid. Retrieved 2014-02-15.
  5. 1 2 Schep LJ, Slaughter RJ, Vale JA, Beasley DM, Gee P (March 2011). "The clinical toxicology of the designer "party pills" benzylpiperazine and trifluoromethylphenylpiperazine". Clin Toxicol . 49 (3): 131–41. doi:10.3109/15563650.2011.572076. PMID   21495881. S2CID   42491343.
  6. 1 2 3 4 Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (March 2005). "N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy')". Neuropsychopharmacology. 30 (3): 550–60. doi: 10.1038/sj.npp.1300585 . PMID   15496938. S2CID   24217984.
  7. Robertson DW, Bloomquist W, Wong DT, Cohen ML (1992). "mCPP but not TFMPP is an antagonist at cardiac 5HT3 receptors". Life Sciences. 50 (8): 599–605. doi:10.1016/0024-3205(92)90372-V. PMID   1736030.
  8. Partilla JS, Dempsey AG, Nagpal AS, Blough BE, Baumann MH, Rothman RB (October 2006). "Interaction of amphetamines and related compounds at the vesicular monoamine transporter". Journal of Pharmacology and Experimental Therapeutics. 319 (1): 237–46. CiteSeerX   10.1.1.690.6669 . doi:10.1124/jpet.106.103622. PMID   16835371. S2CID   22730478.
  9. Yarosh HL, Katz EB, Coop A, Fantegrossi WE (November 2007). "MDMA-like behavioral effects of N-substituted piperazines in the mouse". Pharmacology Biochemistry and Behavior. 88 (1): 18–27. doi:10.1016/j.pbb.2007.06.007. PMC   2082056 . PMID   17651790.
  10. 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 trifluorophenylmethylpiperazine (TFMPP)" (PDF). Centre for Social and Health Outcomes Research and Evaluation (SHORE). Archived from the original (PDF) on 2007-03-18. Retrieved 2007-04-14.
  11. "SOR/2012-65 March 30, 2012 Controlled Drugs and Substances Act". Canada Gazette. Government of Canada. Retrieved 15 September 2014.
  12. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
  13. "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 1129/2015".
  14. "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 225/2017".
  15. "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 733/2021".
  16. "Misuse of Drugs (Classification of BZP) Amendment Bill 2008".
  17. "Erowid TFMPP Vault : Legal Status". Erowid.
  18. "RO 2010 4099". Fedlex. Retrieved 2022-08-16.
  19. "RO 2011 2595". Fedlex. Retrieved 2022-08-16.
  20. "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  21. "Scheduling Actions 2002". U.S. Department of Justice, Drug Enforcement Administration (DEA). Archived from the original on 2003-01-02.
  22. 1 2 Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL