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Trifluoromethylphenylpiperazine (TFMPP)
An Entheogenic Entactogen
by Markus Berger
Nov 2003
Edited, HTML, Published by Erowid.org
Citation:   Berger M. "Trifluoromethylphenylpiperazine (TFMPP): An Entheogenic Entactogen". Erowid.org, Nov 2003: Erowid.org/chemicals/piperazines/tfmpp_article1.shtml.
The following article has been adapted from a piece that appeared in the October 2002 issue of Entheogene Blätter - the German version of The Entheogen Review. Although the few psychonautical reports included in this article present predominantly positive accounts of the effects of TFMPP, a general survey of the web shows more mixed opinions, and we presented largely negative reports in a past discussion of the piperazine compounds; see The Entheogen Review 9(3):143-145. -Eds.


The fact that every day new psychoactive substances are being syntheticized really isn't anything new. Almost constantly so-called "designer drugs" are developed. Phenethylamines and tryptamines have been important players in this arena, and for a few years now piperazines have been gaining status. How important are piperazines to the psychonautics scene, and what manner of effects do they have?

Consider the hip new drug trifluoromethylphenylpiperazine (TFMPP). Surprisingly, it has been reported by some to produce effects that are usually caused by entactogens such as MDMA.

1-(3-trifluoromethylphenyl)piperazine is also known by the names N-(alpha,alpha,alpha-trifluoro-m-tolyl)piperazine, m-trifluormethylphenylpiperazine, TMFPP, TFMPP, and Molly [Note that Molly is also a term used for Ecstasy - Ed.]. Its chemical formula is C11H13F3N2, and its CAS number is 15532-75-9. For storage purposes, it should be kept in a closed and dark place at a temperature of 15 to 30° C. TFMPP is a piperazine derivative. Piperazines (also: diethylendiamines) are hygroscopic (= attract water) and heterocyclic (= contain other atoms in its cycle of carbon) compounds that have antibiotic effects. They are primarily used in veterinary medicine. Piperazines are given to chickens and pigs to control parasites such as worms (Verordnung 1990). Pharmacologically, trifluoromethylphenylpiperazine behaves in a similar manner to phenethylamines (MDMA, MDE, 2-CB, etc.) - it combines with several receptors of the 5-HT-group (serotonin-receptors; 5-HT = 5-hydroxytryptamine = serotonin).

The psychoactive effect caused by a dose taken of TFMPP is sometimes described as being somewhere between empathogens such as MDMA and entheogens such as psilocybin, mescaline, or LSD. With closed eyes, psychoptic effects are found in most cases that involve partly colored visions and patterns similar to those caused by mescaline. One's feelings may seem to be exposed, more intense, more understandable, and somehow almost touchable. However, what is considered "an active dose" of TFMPP can be highly variable and depends on the kind of effects desired. Slight empathogenic effects can be expected by taking a dose of approximately 25 mg. For a more entheogenic or visionary experience, one needs to take 75 -105 mg. Unwanted side effects may include reactions of the skin, diarrhoea or soft stool, hyperthermia (increased temperature of the body), tachycardia (increased number of heart beats), nausea, and vomiting. The Internet newsgroup alt.drugs.chemistry contains some psychonautical reports of experiences with this interesting piperazine. There is the 1997 example of Tom Kasper who owned Chemical Resale of Santa Barbara - a no longer extant company that sold psychoactive "research chemicals". [Kasper eventually did some time in jail and could still be imprisoned for all we know. -Eds.] "By accident", Kasper poured about 100 mg of TFMPP hydrochloride onto a piece of chicken that was supposed to be his dinner (from rhodium/pharmacology/phenylpiperazines.txt):
"[…W ]hen i bit own on that chicken leg, I tasted the bitter taste, but too late. I had already swallowed … This was tuesday afternoon at about 5:00 pm, and I was scheduled to go to the Carlos Santana concert at the Santa Barbara County Bowl at 6:30 pm. What to do, what to do? Well, I couldn't dissapoint my beautiful date … I decided not to say anything. I stopped wedgeing on the chicken and left it out on the workbench (a mistake). When my beautiful date arrived, she saw the chicken and decided to have a bite. She too accidentally ingested a little which must have accidentally spilled on another piece of chicken. Oh well … We arrived at the S.B.C.B. for the concert feeling no effect from the ingestion at about 6:30 pm. By the time Santana started playing however, we were feeling the effect of the accidental ingestion of chemical TFMPP … In my estimation, it was similar to, but MORE euphoriant than MDMA which I had accidentally ingested some years back, when it was still legal. The toxic symptoms of ingestion included:
  1. Increased socialibility
  2. Increased desire to touch and love
  3. Enhanced tactile sensations (it felt good to touch things)
  4. A feeling of "oneness" with the crowd, and with my date
  5. A desire to be very close and to share love with my date"
The effects described in this report are very similar to those of a substance that would be classified as typically entactogenic. [Keep in mind that this largely positive bioassay was reported by someone who at that time earned his living by selling the compound that he was describing effects for, among other similar compounds. -Eds.] There wasn't any visionary component - perhaps the actual dose consumed was too small to produce such effects? Unfortunately, the report isn't crystal clear on exactly what amount of the chemical was comsumed. Due to this vagueness, I've quoted another report of a trip that was posted in the same newsgroup (at the same URL noted earlier); this time there are precise details about the dose.
"I ate 100 mg in a gelcap. I started to feel trippy effects a little before the one hour point, and effects reached full intensity by around 2.5 hours. The comedown began at the 5 or 6 hour point and I was not completely back to normal until 11 or 12 hours. Quite simply, it was not MDMA. There were some skin sensations that seemed like they could be MDMA-like, but there was none of the incredible emotional release of MDMA. However, there was no question that I was tripping. My thought patterns were trippy, things would breathe slightly if I looked very carefully for it, and music had a trippy edge. A little marijuana seemed to enhance the effects some. My pupils were dilated, my jaw was clenched just a little towards the end of the trip, and I was quite thirsty - at least the physical effects were similar to MDMA."
Referring to risks and dangers, the quote below reports on a problem that arose due to the method of ingestion. The author of the following text prepared a sugar lump with about 102 milligrams of TFMPP hydrochloride and let it dissolve under the tongue (http://leda.lycaeum.org/?ID=5429).
"I made the mistake of taking the "sublingual" stance too literally and held the cube in my mouth for a minute or two -for twenty minutes or so afterward my mouth was essentially numb. The substance seems highly caustic and swallowing it in a gelcap with a glass of water probably would've been a cleverer way of ingestion."
Before I define my own experiences I'd like to show you a trip report, which is written by an "anonymous friend" (http://leda.lycaeum.org/?ID=15124) and gives another impression of the effects of TFMPP:
"My alter ego has been conducting experiments with several drugs in the Piperazine family for several months now. Initially, the interest was driven by a desire to find an uncontrolled drug with MDMA action. The futility of this hit him and he has since moved to a more pure, and less applied, view of these experiments.

The following trip report occured recently and involved a friend of my alter ego. His name is A and is very experienced with drugs in the tryptamine, phenetheylamine, and piperazine familes (along with ergot derivatives and non-alkaloid substances). The drug in question is 1-(3-Trifluoromethylphenyl)piperazine monohydrochloride at a dosage of 60 mg. The subject is a 23 year old male who is very thin, weighing in at about 120 lbs.

TFMPP, ~ 60 mg
Time of accidental ingestion by friend: 3:15pm
Time of Written Description of toxic effects from friend: 10:30 - 11:00pm (T+8h)
I'm at the level where I could sleep if I wanted to right now. I have to stay awake for J to come over and we'll hang out for an hour or so, but I'm sure the part of this experience that would have made sleep impossible is long gone. My pupils are still dilated, and I am still feeling little waves of some perceptual shift, but the waves are becoming fewer and further between ... also less intense. I think that a mood elevation was definitely one of the more primary effects. It was very subtile and mild in terms of visual trippiness or any kind of "trippy headspace". It seemed to soften the trademark "self-conscious" effect that kills the buzz for so many other psychedelics. One note on the visuals, the first and last of the noticeable visuals seem to be a "dimming" of light and of visual clarity. Things get a little dim, like the power is waning or something, and then things get brighter again, but my vision also seems to go in and out of some kind of liquid blurriness. I am definitely able to pick out the effects of TFMPP, and it is really nothing like BZP except for the mood elevation. The CNS stimulation was barely evident ... and I think it probably was a side effect of the mood elevation and anticipation. There also is no parallel between the TFMPP and anything anywhere near MDMA. I would place it more like a small but perceivable amount of LSD, without the self concious feeling and clenching, etc.

It's 11:03 now, and I'm sure the effects are dimished to a slight afterglow. The slow nature of the drug would have me thinking it will continue to decline in effect for another 2 hours or so until it isn't noticeable any more. I guess I consider this a positive experience, it was very entertaining. Any more would be overboard, the appetite issues and stomach uncertainty would probably increase with dosage. A Ralph Nader type of political protest would really hit the spot."
What are the experiences of the author?
I took TFMPP exactly three times. My first very cautious, timid experiment (because of a possible allergic reaction or other trouble) with 25 mg of this compound was a disappointment and without any effect. I felt only a little weary. The second experiment was with 80 mg. This dosage induced within two hours soft empathogenic feelings combined with mild and pleasant optical effects that I know from substances like 2C-B. Some objects were more lightened with a 3D picture-like contour in red, green, and yellow. My feelings were agreeable and I was in a very good mood but my mind wasn't satisfied enough. So I began to smoke a lot of hashish and after half an hour I took my last LSD trip. TFMPP at a dosage of 80 mg was a nice and short experience, not more.

My last experience in 2002 with 130 mg of TFMPP was on a much higher level. I took the 130 mg at 6:00pm. Approximately at 7:30 I felt the same soft effects like last time, but with more hallucinogenic symptoms. The skin around my eyes was very tight, my pupils were dilated and shaky (nystagmus) and my thinking was much clearer and very deep but harder to sort. At 8:00 the trip had found its peak. At 12:20 or so the effects declined slowly, at 1:00 I went to bed and slept deeply until the late morning. The chief characteristic of the trip was the visual component, that impress me extraordinary. The physically effect was a kind of hyperthermia (I felt a little feverish) and tachycardia (sometimes more than 140 heartbeats per minute!). The main TFMPP effect cannot be compared to other entheogens/empathogens - but if I have to, I would say it's eventually like a mixture of 2C-B with MDA. Sometimes I felt like loosing control about myself for a moment. The trip is very hard to explain ... The most significant sign, and I say it again, is the psychoptical effect. It's a colorful and more subconscious than conscious reflected trip. I think I will have some more experiences with this substance in the future.

TFMPP began to gain notoriety within the rave community and in the USA the DEA eventually scheduled the substance on September 20th 2002. It has been banned not only from being used for hedonistic reasons but also for therapeutical purposes in the U.S. (DEA 2002). As with most cases when one drug is repressed, a new on pops up to take its place. In this case, 1-(3-Chlorophenyl)piperazin or 3-CPP, a close relative of TFMPP, has appeared on the market. It is not scheduled by name, although it may be considered illegal under the Controlled Substance Analog laws if it was possessed with an intention to consume. 3-CPP has milder effects, and it is believed that it will soon be available on the European market. TFMPP is still being sold via the Internet, and consumed as a substitute for MDMA. Since American "drug warriors" have scheduled the compound, it is now being synthesized in underground laboratories for the black market. It is offered in powder, liquid, and/or colored pills with symbols on it, and are it is either marketed straightforwardly as TFMPP or misrepresented as MDMA (DEA 2001a; DEA 2001b). According to the DEA there has been one death already: a young woman from Zürich is said to have died from a combination of a piperazine derivate and MDMA. However, there is no source cited for this data, so this report is suspect (DEA 2002).

TFMPP can still be purchased via the Internet. It has been legally produced in India and can be ordered from all over the world in amounts from 5 to 25 grams, ranging in price from $30.00 to $130.00. The pure substance is also available in Germany for 10 to 200 euros. Mail order sources for this chemical include SynChem OHG in Kassel, LM Chemical Trade & Consulting GmbH in Prisdorf, Merck KgaA in Darmstadt, and CHESS GmbH in Mannheim. Orders can be made via the Internet or snail mail; prices vary depending on the source. CHESS GmbH offers the best price - 80 euros for 25 grams of pure TFMPP. (Another business charges 114 euros for a mere 10 grams of TFMPP). Although at the moment TFMPP is legal outside of the USA, it is impossible to say for how long this will continue. Unfortunately, articles like this one may contribute to its being scheduled in other countries.

On March 21, 2003 the DEA published "Safety Advisory Regarding New Club Drug 'Molly'", an interesting piece of news that I want to cite completely (DEA 2003):

"Safety Advisory Regarding New Club Drug 'Molly'

Detroit, MI- Special Agents of the U.S. Drug Enforcement Administration (DEA) working with the Michigan State Police and local law enforcement agencies have recently discovered the presence of a new club drug that is being sold to high school and college age students at "Rave" parties throughout the Detroit and Ann Arbor areas. This substance is known on the street as "Molly", which is 1-(3-Trifluoromethylphenyl) piperazine (TFMPP).

This is an extremely dangerous drug, which is clandestinely manufactured and marketed in "Rave Clubs" as a more intense form of Ecstasy. This drug is an off-white powder generally sold in a gelatin capsule. TFMPP and Benzylpiperazine (BZP) were both given emergency controlled substance scheduling by the U.S. Drug Enforcement Administration in September 2002. TFMPP was given Schedule I status, meaning it has a high potential for abuse and no accepted medical use. This drug first appeared on the West Coast of the United States and these recent seizures in Michigan are the first indication of its presence in the metropolitan Detroit area. TFMPP also goes by the names "legal E", "legal X" or "A2". TFMPP can cause increased heart rate, blood pressure and body temperature.

"Molly" has properties similar to the stimulant effects of Ecstasy, but taken in larger doses it promotes hallucinogenic reactions. This poses an even greater risk to young adults who have taken Ecstasy previously and accidentally overdose by trying to achieve the hallucinogenic effects. DEA is currently conducting "Operation X-Out", which is a nationwide initiative to increase education and enforcement operations involving club and predatory drugs. Drug distributors have invaded the Internet with misinformation regarding the dangers of club and "date rape" drugs that are marketed toward young people. Effective information campaigns are essential to inform young Americans about club drugs such as GHB, Ecstasy, Ketamine and TFMPP, which are promoted by individuals who disguise their deadly effects.

"This is another example of individuals exploiting our young people with dangerous mixtures of chemicals that have the potential for deadly consequences. The DEA working closely with state and local law enforcement agencies, will do everything in our power to protect our children," said Michael A. Braun, Special Agent in Charge of the DEA Detroit Field Division."
Please remember, that there is a mistake in the text above. The synonym "A2" is not a name for TFMPP but for BZP (N-benzylpiperazine). Some short informations on A2 you find below.

Piperazine Candyflipping
A mixture of TFMPP and A2 called Combo or Exodus is being sold on the black market. A2 (see below) is thought to add an MDMA-like acceleration to the trippy effects of TFMPP. Moreover, the A2 component is said to improve the effects of TFMPP on emotions, but I cannot confirm this. TFMPP alone stimulates the universe of emotions on a large scale. The effect of TFMPP and A2 at a dose of 150 to 200 milligrams tends to be more similar to the effects of amphetamines referring to the effects of pure TFMPP. At the moment, both substances are legal everywhere except in the USA. There have been no adverse contraindications reported between the two substances when combined, so far as we are aware. A very good explanation of the effects of Combo is published in The Entheogen Review IX (3):
"The combination of benzylpiperazine and another piperazine - 1-(3-trifluoromethyphenyl)piperazine (or TFMPP), in a ratio of about 2:1 appears to be fairly common. On the positive side, this combination has been described as having entactogenic body-effects similar to MDMA and/or MDEA, but generally without the strong empathogenic qualities of these phenethylamines. A meditative quietness, calm centeredness, contentedness, a warm flushing sensation, waves of euphoria, tactile pleasure, time dilation, and mild visual effects (similar to low-dose mescaline, LSD, or 2C-T-2) have also been reported. (Comparisons to a 30-50 mg dose of MDMA or clean LSD without the visuals have been made.) On the negative side, this combination has resulted in nystagmus, dehydration, jaw-clench, mild to severe nausea, vomiting, toxic psychosis (panic and extreme paranoia), high blood pressure, persistent headache, flu-like symptoms, spaciness, stiff neck, post-trip exhaustion, and a hangover lasting several days." (A.S. 2000)
If you're interested in other reports of TFMPP combo trips go to http://leda.lycaeum.org/?ID=416

What is A2?
A2 is N-benzylpiperazine, also known as "BZP" and synonymous with 1-benzyl-1,4-diazacyclohexane-dihydrochloride. Its formula is C11H16N2. In 1944 it was synthetizised for use in veterinary medicine. It is reported to cause an effect similar to methamphetamine. The usual dose is between 150 and 500 milligrams, and the effects last for 6 to 10 hours.



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