Trifluoromethylphenylpiperazine

{{Short description|Serotonergic drug}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = changed | verifiedrevid = 470614581 | drug_name = TFMPP | image = TFMPP.svg | image_class = skin-invert-image | width = 225px | image2 = TFMPP-3D-vdW.png | image_class2 = bg-transparent | width2 = 200px

| tradename = | pregnancy_category = | routes_of_administration = Oral | class = Non-selective serotonin receptor agonist; Serotonin 5-HT1B receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonin 5-HT2C receptor agonist; Serotonin releasing agent | ATC_prefix = None | ATC_suffix =

| legal_AU = S9 | legal_BR = F2 | legal_BR_comment = <ref>{{cite web | author = Anvisa | date = 2023-07-24 | title = RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial | language = pt-BR | publisher = Diário Oficial da União | url = https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 | access-date = 2023-08-27 | archive-date = 2023-08-27 | archive-url = https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 | author-link = Brazilian Health Regulatory Agency | trans-title = Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control | url-status = live | publication-date = 2023-07-25 }}</ref> | legal_CA = Schedule III | legal_DE = Anlage II | legal_US = Scheduled in Florida; Unscheduled Federally | legal_NZ = Class C | legal_status = II-P (Poland)<ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | publisher = Internetowy System Aktów Prawnych | url = http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614 | access-date = 17 June 2011 }}</ref>

| CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 15532-75-9 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 25R3ONU51C | PubChem = 4296 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4145 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 83536 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C22745 | synonyms = ''m''-Trifluoromethylphenylpiperazine; 3-Trifluoromethylphenylpiperazine; TFMPP; mTFMPP

| IUPAC_name = 1-[3-(trifluoromethyl)phenyl]piperazine | C=11 | H=13 | F=3 | N=2 | SMILES = FC(F)(F)C1=CC(N2CCNCC2)=CC=C1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = VZUBMIDXJRGARE-UHFFFAOYSA-N }}

'''''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").<ref>{{cite web | title = Erowid TFMPP Vault: Basics | publisher = Erowid | url = https://www.erowid.org/chemicals/tfmpp/tfmpp_basics.shtml | access-date = 2014-02-15 }}</ref><ref name="Schep2011">{{cite journal | vauthors = Schep LJ, Slaughter RJ, Vale JA, Beasley DM, Gee P | date = March 2011 | title = The clinical toxicology of the designer "party pills" benzylpiperazine and trifluoromethylphenylpiperazine | journal = Clinical Toxicology | volume = 49 | issue = 3 | pages = 131–141 | doi = 10.3109/15563650.2011.572076 | pmid = 21495881 | s2cid = 42491343 }}</ref>

==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.<ref name="pmid15496938"/> More commonly, TFMPP is co-administered with BZP, which acts as a norepinephrine and dopamine releasing agent.<ref>{{cite journal | vauthors = Partilla JS, Dempsey AG, Nagpal AS, Blough BE, Baumann MH, Rothman RB | date = October 2006 | title = Interaction of amphetamines and related compounds at the vesicular monoamine transporter | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 319 | issue = 1 | pages = 237–246 | doi = 10.1124/jpet.106.103622 | pmid = 16835371 | citeseerx = 10.1.1.690.6669 | s2cid = 22730478 }}</ref> 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.<ref>{{cite journal | vauthors = Yarosh HL, Katz EB, Coop A, Fantegrossi WE | date = November 2007 | title = MDMA-like behavioral effects of N-substituted piperazines in the mouse | journal = Pharmacology, Biochemistry, and Behavior | volume = 88 | issue = 1 | pages = 18–27 | doi = 10.1016/j.pbb.2007.06.007 | pmc = 2082056 | pmid = 17651790 }}</ref>

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".<ref name="JanLinLee2010">{{cite journal | vauthors = Jan RK, Lin JC, Lee H, Sheridan JL, Kydd RR, Kirk IJ, Russell BR | date = August 2010 | title = Determining the subjective effects of TFMPP in human males | journal = Psychopharmacology | volume = 211 | issue = 3 | pages = 347–353 | doi = 10.1007/s00213-010-1911-y | pmid = 20552171 }}</ref><ref name="LinJanKydd2011">{{cite journal | vauthors = Lin JC, Jan RK, Kydd RR, Russell BR | date = September 2011 | title = Subjective effects in humans following administration of party pill drugs BZP and TFMPP alone and in combination | journal = Drug Testing and Analysis | volume = 3 | issue = 9 | pages = 582–585 | doi = 10.1002/dta.285 | pmid = 21538945 }}</ref> 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.<ref name="JanLinLee2010" /><ref name="LinJanKydd2011" /> The combination of TFMPP with BZP crudely mimics the effects of MDMA in clinical studies.<ref name="LinJanKydd2011" /><ref name="LinJanLee2011">{{cite journal | vauthors = Lin JC, Jan RK, Lee H, Jensen MA, Kydd RR, Russell BR | date = April 2011 | title = Determining the subjective and physiological effects of BZP combined with TFMPP in human males | journal = Psychopharmacology | volume = 214 | issue = 3 | pages = 761–768 | doi = 10.1007/s00213-010-2081-7 | pmid = 21060995 }}</ref>

==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,<ref name="Schep2011"/> 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.<ref>{{cite web | vauthors = Wilkins C, Girling M, Sweetsur P, Huckle T, Huakau J | title = Legal party pill use in New Zealand: Prevalence of use, availability, health harms and 'gateway effects' of benzylpiperazine (BZP) and trifluorophenylmethylpiperazine (TFMPP) | publisher = Centre for Social and Health Outcomes Research and Evaluation (SHORE) | url = http://www.spiritualhigh.co.uk/spiritualhigh.co.uk/downloads/Legal-party-pills-in-New-Zealand-report.pdf | access-date = 2007-04-14 | archive-date = 2007-03-18 | archive-url = https://web.archive.org/web/20070318042503/http://www.spiritualhigh.co.uk/spiritualhigh.co.uk/downloads/Legal-party-pills-in-New-Zealand-report.pdf | url-status = usurped }}</ref>{{unreliable source?|date=February 2015}}

==Pharmacology== ===Pharmacodynamics=== thumb|190px|right|class=skin-invert-image|4-HO-TFMPP is a metabolite of TFMPP.<ref>{{cite web | title = 4-(Piperazin-1-yl)-2-(trifluoromethyl)phenol | url = https://pubchem.ncbi.nlm.nih.gov/compound/86055599#section=Transformations&fullscreen=true }}</ref>

TFMPP has affinity for the 5-HT1A (Ki = 288–1,950 nM), 5-HT1B (Ki = 30–132 nM), 5-HT1D (Ki = 282 nM), 5-HT2A (Ki = 160–269 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.<ref name="pmid15496938">{{cite journal | vauthors = Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB | date = March 2005 | title = N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy') | journal = Neuropsychopharmacology | volume = 30 | issue = 3 | pages = 550–560 | doi = 10.1038/sj.npp.1300585 | pmid = 15496938 | s2cid = 24217984 | doi-access = free }}</ref><ref name="Glennon1987">{{cite journal | vauthors = Glennon RA | date = January 1987 | title = Central serotonin receptors as targets for drug research | journal = Journal of Medicinal Chemistry | volume = 30 | issue = 1 | pages = 1–12 | doi = 10.1021/jm00384a001 | pmid = 3543362 | quote = Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites }}</ref> Unlike the related piperazine compound ''meta''-chlorophenylpiperazine (mCPP), TFMPP has insignificant affinity for the 5-HT3 receptor (IC50 = 2,373 nM).<ref name="pmid1736030">{{cite journal | vauthors = Robertson DW, Bloomquist W, Wong DT, Cohen ML | year = 1992 | title = mCPP but not TFMPP is an antagonist at cardiac 5HT3 receptors | journal = Life Sciences | volume = 50 | issue = 8 | pages = 599–605 | doi = 10.1016/0024-3205(92)90372-V | pmid = 1736030 }}</ref> TFMPP also binds to the SERT (EC50 = 121 nM) and evokes the release of serotonin.<ref name="pmid15496938"/> It has no effects on dopamine or norepinephrine reuptake or efflux.<ref name="pmid15496938"/>

Findings are mixed on whether TFMPP produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, with some studies finding that it does and others reporting that it does not.<ref name="YaroshKatzCoop2007">{{cite journal | vauthors = Yarosh HL, Katz EB, Coop A, Fantegrossi WE | date = November 2007 | title = MDMA-like behavioral effects of N-substituted piperazines in the mouse | journal = Pharmacology, Biochemistry, and Behavior | volume = 88 | issue = 1 | pages = 18–27 | doi = 10.1016/j.pbb.2007.06.007 | pmc = 2082056 | pmid = 17651790 }}</ref><ref name="VickersEastonMalcolm2001">{{cite journal | vauthors = Vickers SP, Easton N, Malcolm CS, Allen NH, Porter RH, Bickerdike MJ, Kennett GA | date = 2001 | title = Modulation of 5-HT(2A) receptor-mediated head-twitch behaviour in the rat by 5-HT(2C) receptor agonists | journal = Pharmacology, Biochemistry, and Behavior | volume = 69 | issue = 3–4 | pages = 643–652 | doi = 10.1016/s0091-3057(01)00552-4 | pmid = 11509227 }}</ref><ref name="SchreiberBroccoAudinot1995">{{cite journal | vauthors = Schreiber R, Brocco M, Audinot V, Gobert A, Veiga S, Millan MJ | date = April 1995 | title = (1-(2,5-dimethoxy-4 iodophenyl)-2-aminopropane)-induced head-twitches in the rat are mediated by 5-hydroxytryptamine (5-HT) 2A receptors: modulation by novel 5-HT2A/2C antagonists, D1 antagonists and 5-HT1A agonists | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 273 | issue = 1 | pages = 101–112 | doi = 10.1016/S0022-3565(25)09485-6 | pmid = 7714755 }}</ref><ref name="SimanskySchechter1988">{{cite journal | vauthors = Simansky KJ, Schechter LE | date = December 1988 | title = Properties of some 1-arylpiperazines as antagonists of stereotyped behaviors mediated by central serotonergic receptors in rodents | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 247 | issue = 3 | pages = 1073–1081 | doi = 10.1016/S0022-3565(25)13260-6 | pmid = 3144595 }}</ref> In one study, TFMPP did not produce the head-twitch response on its own, but when combined with the selective serotonin 5-HT2C receptor antagonist SB-242084, it was able to dose-dependently induce head twitches.<ref name="VickersEastonMalcolm2001" /> In contrast to the preceding findings, the drug has been found to dose-dependently antagonize the head-twitch response induced by serotonergic psychedelics like DOI.<ref name="VickersEastonMalcolm2001" /><ref name="SchreiberBroccoAudinot1995" /><ref name="BerendsenBroekkamp1990">{{cite journal | vauthors = Berendsen HH, Broekkamp CL | date = November 1990 | title = Behavioural evidence for functional interactions between 5-HT-receptor subtypes in rats and mice | journal = British Journal of Pharmacology | volume = 101 | issue = 3 | pages = 667–673 | doi = 10.1111/j.1476-5381.1990.tb14138.x | pmc = 1917735 | pmid = 2150180 }}</ref><ref name="SimanskySchechter1988" /> The preceding findings suggest that serotonin 5-HT2C receptor activation inhibits and can mask the head-twitch response induced by serotonin 5-HT2A receptor agonists.<ref name="VickersEastonMalcolm2001" />

TFMPP has been found to reduce aggression in rodents.<ref name="OlivierMosvanOorschot1995">{{cite journal | vauthors = Olivier B, Mos J, van Oorschot R, Hen R | date = October 1995 | title = Serotonin receptors and animal models of aggressive behavior | journal = Pharmacopsychiatry | volume = 28 Suppl 2 | pages = 80–90 | doi = 10.1055/s-2007-979624 | pmid = 8614705 }}</ref><ref name="MuehlenkampLucionVogel1995">{{cite journal | vauthors = Muehlenkamp F, Lucion A, Vogel WH | date = April 1995 | title = Effects of selective serotonergic agonists on aggressive behavior in rats | journal = Pharmacology, Biochemistry, and Behavior | volume = 50 | issue = 4 | pages = 671–674 | doi = 10.1016/0091-3057(95)00351-7 | pmid = 7617717 }}</ref> TFMPP was not self-administered by rhesus monkeys, suggesting that it lacks reinforcing effects.<ref name="FantegrossiWingerWoods2005">{{cite journal | vauthors = Fantegrossi WE, Winger G, Woods JH, Woolverton WL, Coop A | date = February 2005 | title = Reinforcing and discriminative stimulus effects of 1-benzylpiperazine and trifluoromethylphenylpiperazine in rhesus monkeys | journal = Drug and Alcohol Dependence | volume = 77 | issue = 2 | pages = 161–168 | doi = 10.1016/j.drugalcdep.2004.07.014 | pmid = 15664717 }}</ref>

===Pharmacokinetics=== The pharmacokinetics of TFMPP have been studied.<ref name="AntiaTingleRussell2010">{{cite journal | vauthors = Antia U, Tingle MD, Russell BR | date = September 2010 | title = Validation of an LC-MS method for the detection and quantification of BZP and TFMPP and their hydroxylated metabolites in human plasma and its application to the pharmacokinetic study of TFMPP in humans | journal = Journal of Forensic Sciences | volume = 55 | issue = 5 | pages = 1311–1318 | doi = 10.1111/j.1556-4029.2010.01457.x | pmid = 20533987 }}</ref>

==Chemistry== ===Synthesis=== The chemical synthesis of TFMPP has been described.<ref name="ShulginManningDaley2011">{{cite book | vauthors = Shulgin A, Manning T, Daley PF | year = 2011 | title = The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | publisher = Transform Press | volume = 1 | isbn = 978-0-9630096-3-0 | location = Berkeley }}</ref>

===Derivatives=== * Antrafenine * CPD-1

==History== TFMPP was first described in the scientific literature in 1978.<ref name="FullerSnoddyMason1978">{{cite journal | vauthors = Fuller RW, Snoddy HD, Mason NR, Molloy BR | date = November 1978 | title = Effect of 1-(m-trifluoromethylphenyl)-piperazine on 3H-serotonin binding to membranes from rat brain in vitro and on serotonin turnover in rat brain in vivo | journal = European Journal of Pharmacology | volume = 52 | issue = 1 | pages = 11–16 | doi = 10.1016/0014-2999(78)90016-x | pmid = 720384 }}</ref>

==Society and culture== ===Legal status=== ====Canada==== Since 2012, TFMPP has been listed as a Schedule III controlled substance in Canada,<ref>{{cite web | title = SOR/2012-65 March 30, 2012 Controlled Drugs and Substances Act | website = Canada Gazette | publisher = Government of Canada | url = http://gazette.gc.ca/rp-pr/p2/2012/2012-04-11/html/sor-dors65-eng.html#archived | access-date = 15 September 2014 }}</ref> 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.<ref>{{cite web | date = 27 September 2015 | title = 关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | language = zh | publisher = China Food and Drug Administration | url = http://www.sfda.gov.cn/WS01/CL0056/130753.html | access-date = 1 October 2015 }}</ref>

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

====Finland==== Scheduled in government decree on psychoactive substances banned from the consumer market.<ref>{{cite web | title = FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 1129/2015 | url = https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2015/1129 }}</ref><ref>{{cite web | title = FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 225/2017 | url = https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2017/225 }}</ref><ref>{{cite web | title = FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 733/2021 | url = https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2021/733 }}</ref>

====Japan==== Since 2003, TFMPP and BZP became illegal in Japan.

====Netherlands==== TFMPP is unscheduled in the Netherlands. <ref>{{cite web | vauthors = Weed A | date = 2023-10-18 | title = Trifluoromethylphenylpiperazine | language = en-US | url = https://researchem.net/trifluoromethylphenylpiperazine/ | access-date = 2026-03-19 }}</ref>

====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.<ref>{{cite web | title = Misuse of Drugs (Classification of BZP) Amendment Bill 2008 | url = http://www.parliament.nz/en-NZ/PB/Legislation/Bills/d/3/d/00DBHOH_BILL8220_1-Misuse-of-Drugs-Classification-of-BZP-Amendment.htm }}</ref>

====Sweden==== As of March 1, 2006, TFMPP is scheduled as a "dangerous substance" in Sweden.<ref>{{cite web | title = Erowid TFMPP Vault : Legal Status | publisher = Erowid | url = https://www.erowid.org/chemicals/tfmpp/tfmpp_law.shtml }}</ref>

====Switzerland==== As of December 1, 2010, TFMPP is a controlled substance in Switzerland.<ref>{{cite web | title = RO 2010 4099 | publisher = Fedlex | url = https://fedlex.data.admin.ch/eli/oc/2010/599 | access-date = 2022-08-16 }}</ref><ref>{{cite web | title = RO 2011 2595 | publisher = Fedlex | url = https://www.fedlex.admin.ch/eli/cc/2011/363/fr | access-date = 2022-08-16 }}</ref>

====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,<ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">{{cite web | title = §1308.11 Schedule I. | url = http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm | access-date = 2014-12-17 | archive-date = 2009-08-27 | archive-url = https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm | url-status = dead }}</ref> but it was briefly emergency scheduled in Schedule I. The scheduling expired in April 2004 and was not renewed.<ref>{{cite web | title = Scheduling Actions 2002 | publisher = U.S. Department of Justice, Drug Enforcement Administration (DEA) | url = http://www.deadiversion.usdoj.gov/fed_regs/sched_actions/2002/fr09202.htm | archive-date = 2003-01-02 | archive-url = https://web.archive.org/web/20030102043925/http://www.deadiversion.usdoj.gov/fed_regs/sched_actions/2002/fr09202.htm | url-status = dead }}</ref> However, some states such as Florida have banned the drug in their criminal statutes making its possession a felony.<ref name="Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL">[http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL]</ref>

=====Florida===== TFMPP is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.<ref name="Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL"/>

=====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.

== See also == * Substituted piperazine

== References == {{Reflist}}

== External links == * [https://isomerdesign.com/pihkal/explore/803 TFMPP - Isomer Design] * [https://www.erowid.org/chemicals/tfmpp/tfmpp.shtml TFMPP - Erowid] * [https://archive.org/details/shulgin-index-vol-1/page/283/mode/1up?view=theater mTFMPP - The Shulgin Index]

Category:5-HT1A agonists Category:5-HT1B agonists Category:5-HT1D agonists Category:5-HT2A agonists Category:5-HT2C agonists Category:Antiaggressive drugs Category:Designer drugs Category:1-Piperazinyl compounds Category:Psychedelic arylpiperazines Category:Serotonin receptor agonists Category:Serotonin releasing agents Category:meta-Trifluoromethylphenylpiperazines