Trifluoromethylphenylpiperazine

Structural formula
General
Surname	Trifluoromethylphenylpiperazine
other names	1- (3-trifluoromethylphenyl) piperazine; N - (α, α, α-trifluoro- m -tolyl) -piperazine; m -Trifluoromethylphenylpiperazine; TFMPP;
Molecular formula	C 11 H 13 F 3 N 2
Brief description	yellow oil
External identifiers / databases
EC number	239-574-4
ECHA InfoCard	100,035,962
PubChem	4296
ChemSpider	4145
Wikidata	Q419405
properties
Molar mass	230.23 g · mol -1
Physical state	liquid
density	1.23 g cm −3
boiling point	65–71 ° C (20 hPa )
Vapor pressure	0.25 Pa (25 ° C)
solubility	soluble in water (2.6 g l −1 )
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 302 + 352-304 + 340-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Trifluoromethylphenylpiperazine ( TFMPP ) is an organic, heterocyclic compound. TFMPP is a derivative of piperazine . Because of its psychoactive effects, it appears as an ingredient in party drugs .

use

It appeared as an MDMA substitute or additive in ecstasy tablets, especially in combination with benzylpiperazine (BZP, A2). Other piperazine derivatives have been found as ingredients in recreational drugs , such as methylenedioxybenzylpiperazine (MDBP), meta- chlorophenylpiperazine (mCPP) or MeOPP. TFMPP is not important in chemical synthesis or for industrial applications.

pharmacology

TFMPP binds agonist at serotonin 5-HT _2C - and 5-HT _1B receptors . It also causes a relevant release of serotonin reserves from the vesicles.

TFMPP could be suitable to support the therapy of alcoholism: in animal experiments it shows an inhibitory influence on the absorption of alcohol.

The pharmacodynamic profile of action is similar to that of fenfluramine , which is no longer available in Germany.

Legal status

In the USA, the appearance of TFMPP in recreational drugs prompted the Drug Enforcement Administration (DEA) in 2002 to include the substance in Class I (Schedule I, high potential for abuse, no proven medical benefit, illegal) as a precautionary measure. However, since the potential for abuse turned out to be rather low, the ban was lifted again in April 2004. In the EU, the trade in TFMPP is - as far as possible - monitored critically by the authorities, in Denmark it has already been banned.

Switzerland : With the entry into force of the revised Narcotics Ordinance by Swissmedic on December 1, 2010, TFMPP will be subject to the Narcotics Act and will therefore be illegal from then on. Importation, possession, distribution etc. are punished according to the Narcotics Act.

Metabolism and Detection

TFMPP (present as salt)

There is no chemical detection reaction for TFMPP, and no immunological methods have been developed to date. Detection is therefore only possible with the aid of chromatographic methods such as HPLC, HPLC-MS or GC-MS. The metabolism of TFMPP has been known since 2003. The aromatic is hydroxylated and the piperazine ring also decomposes through dealkylation on both nitrogen atoms, and finally N- hydroxylation.

Individual evidence

↑ Georg Manolikakes, Andrei Gavryushin, Paul Knochel: An Efficient Silane-Promoted Nickel-Catalyzed Amination of Aryl and Heteroaryl Chlorides . In: The Journal of Organic Chemistry . tape 73 , no. 4 , 2008, p. 1429-1434 , doi : 10.1021 / jo702219f .
↑ ^a ^b ^c ^d ^e Data sheet 3- (Trifluoromethyl) -N-phenylpiperazine (PDF) from Merck , accessed on April 24, 2011.
↑ ^a ^b Entry on trifluoromethylphenylpiperazine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ MD Schechter: Use of TFMPP stimulus properties as a model of 5-HT1B receptor activation. In: Pharmacol Biochem Behav . , 31 (1), 1988, pp. 53-7. PMID 3252260 .
^ BA Johnson, N. Ait-Daoud: Neuropharmacological treatments for alcoholism: scientific basis and clinical findings. In: Psychopharmacology , 149, 2000, pp. 327-344. PMID 10867960 .
↑ US Department of Justice, Drug Enforcement Administration (DEA), Scheduling Actions 2002 ( Memento of October 20, 2008 in the Internet Archive )
↑ Text of the Swissmedic Narcotics Ordinance, which came into force on December 1, 2010, as a PDF .
↑ Text of the Swiss Narcotics Act as PDF. Relevant criminal provisions: Art. 19 and following. .
^ RF Staack et al. (2003): New designer drug TFMPP: GC / MS and LC / MS studies on its phase I and II metabolism and on its toxicological detection in rat urine. In: J Mass Spectrom ., 38 (9), pp. 971-81. PMID 14505325 .

[Manolikakes-1] Georg Manolikakes, Andrei Gavryushin, Paul Knochel: An Efficient Silane-Promoted Nickel-Catalyzed Amination of Aryl and Heteroaryl Chlorides . In: The Journal of Organic Chemistry . tape 73 , no. 4 , 2008, p. 1429-1434 , doi : 10.1021 / jo702219f .

[Merck-2] Data sheet 3- (Trifluoromethyl) -N-phenylpiperazine (PDF) from Merck , accessed on April 24, 2011.

[ChemID-3] Entry on trifluoromethylphenylpiperazine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[4] MD Schechter: Use of TFMPP stimulus properties as a model of 5-HT1B receptor activation. In: Pharmacol Biochem Behav . , 31 (1), 1988, pp. 53-7. PMID 3252260 .

[5] BA Johnson, N. Ait-Daoud: Neuropharmacological treatments for alcoholism: scientific basis and clinical findings. In: Psychopharmacology , 149, 2000, pp. 327-344. PMID 10867960 .

[6] US Department of Justice, Drug Enforcement Administration (DEA), Scheduling Actions 2002 ( Memento of October 20, 2008 in the Internet Archive )

[7] Text of the Swissmedic Narcotics Ordinance, which came into force on December 1, 2010, as a PDF .

[8] Text of the Swiss Narcotics Act as PDF. Relevant criminal provisions: Art. 19 and following. .

[9] RF Staack et al. (2003): New designer drug TFMPP: GC / MS and LC / MS studies on its phase I and II metabolism and on its toxicological detection in rat urine. In: J Mass Spectrom ., 38 (9), pp. 971-81. PMID 14505325 .