''para''-Fluorophenylpiperazine (pFPP, 4-FPP, 4-Fluorophenylpiperazine; Fluoperazine, Flipiperazine) is a

piperazine 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. The piperazines are a broad ...

derivative with mildly psychedelic and

euphoriant Euphoria ( ) is the experience (or affect) of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and danci ...

effects. It has been sold as an ingredient in legal

recreational drugs Recreation is an activity of leisure, leisure being discretionary time. The "need to do something for recreation" is an essential element of human biology and psychology. Recreational activities are often done for enjoyment, amusement, or pleasur ...

known as "

Party pills Party pills, also known as "herbal highs", "pep pills" "dance pills" and "natural power", is a colloquialism for a type of recreational drug whose main ingredient was originally benzylpiperazine (BZP), but has expanded to a wide range of compound ...

", initially in

New Zealand New Zealand ( mi, Aotearoa ) is an island country in the southwestern Pacific Ocean. It consists of two main landmasses—the North Island () and the South Island ()—and over 700 smaller islands. It is the sixth-largest island count ...

and subsequently in other countries around the world. pFPP has been found ''

in vitro ''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called " test-tube experiments", these studies in biology ...

'' to act mainly as a 5-HT_1A receptor agonist, with some additional affinity for the 5-HT_2A and 5-HT_2C receptors. It has also been shown to

inhibit Inhibitor or inhibition may refer to: In biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotr ...

the

reuptake Reuptake is the reabsorption of a neurotransmitter by a neurotransmitter transporter located along the plasma membrane of an axon terminal (i.e., the Synapse, pre-synaptic neuron at a synapse) or glial cell after it has performed its function of ...

of serotonin and

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic chemical in the catecholamine family that functions in the brain and body as both a hormone and neurotransmitter. The name "noradrenaline" (from Latin '' ad' ...

, and to possibly induce their

release Release may refer to: * Art release, the public distribution of an artistic production, such as a film, album, or song * Legal release, a legal instrument * News release, a communication directed at the news media * Release (ISUP), a code to iden ...

. pFPP was originally discovered as a metabolite of the hypnotic 5-HT_2A and α₁-adrenergic receptor antagonist

niaprazine Niaprazine ( INN) (brand name Nopron) is a sedative-hypnotic drug of the phenylpiperazine group. It has been used in the treatment of sleep disturbances since the early 1970s in several European countries including France, Italy, and Luxembourg. ...

in 1982, but was rediscovered in 2003 as a potential recreational drug, and sold as an ingredient in "Party pills" in New Zealand, under brand names such as "The Big Grin", "Mashed", and "Extreme Beans". Subsequently it has continued to be used as an ingredient in black market "ecstasy" pills around the world. pFPP has little stimulant effects, with its subjective effects derived mainly from its action as a 5-HT_1A receptor agonist. pFPP is active at doses between 20 and 150 mg, but higher doses cause a range of side-effects such as migraine headaches,

muscle ache Myalgia (also called muscle pain and muscle ache in layman's terms) is the medical term for muscle pain. Myalgia is a symptom of many diseases. The most common cause of Acute disease, acute myalgia is the overuse of a muscle or Muscle group, gro ...

anxiety Anxiety is an emotion which is characterized by an unpleasant state of inner turmoil and includes feelings of dread over anticipated events. Anxiety is different than fear in that the former is defined as the anticipation of a future threat wh ...

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...

, and

vomiting Vomiting (also known as emesis and throwing up) is the involuntary, forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteri ...

. Metabolic studies have shown pFPP to be an inhibitor of various

Cytochrome P450 Cytochromes P450 (CYPs) are a superfamily of enzymes containing heme as a cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are important for the clearance of various co ...

enzymes in the liver which may contribute to its side-effect profile. Based on the recommendation of the EACD, the New Zealand government has passed legislation which placed BZP, along with a number of other piperazine derivatives, 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.Misuse of Drugs (Classification of BZP) Amendment Bill 2008
/ref> This drug has been detected in a drug-facilitated sexual assault case in the United States of America.

References

{{DEFAULTSORT:Fluorophenylpiperazine, para- Phenylpiperazines Entactogens and empathogens Psychedelic drugs Serotonin receptor agonists Monoamine releasing agents Fluoroarenes Designer drugs

See also

References