Piperazines
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Piperazines
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. List of substituted piperazines Benzylpiperazines File:Benzylpiperazine.svg, 1-Benzylpiperazine File:MBZP.svg, 1-Methyl-4-benzylpiperazine File:DBZP.svg, 1,4-Dibenzylpiperazine File:MDBZP.svg, 3,4-Methylenedioxy-1-benzylpiperazine File:2C-B-BZP.svg, 4-Bromo-2,5-dimethoxy-1-benzylpiperazine File:Methoxypiperamide.png, Methoxypiperamide File:Sunifiram.svg , Sunifiram File:3-Methylbenzylpiperazine structure.png, 3-Methylbenzylpiperazine * 1-Benzylpiperazine (BZP) * 1-Methyl-4-benzylpiperazine (MBZP) * 1,4-Dibenzylpiperazine (DBZP) * 3,4-Methylenedioxy-1-benzylpiperazine (MDBZP) * 4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP) * Methoxypiperamide (MeOP, MEXP) ((4-methoxyphenyl)(4-methylpiperazin-1-yl)methanone) * Sunifiram (1-benzoyl-4-propanoylpiperazine) * 3-Methylbenzylpiperazine (3-MeBZP) Befuraline, ...
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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 class of chemical compounds, many with important pharmacological properties, which contain a core piperazine functional group. Origin and naming Piperazines were originally named because of their chemical similarity with piperidine, part of the structure of piperine in the black pepper plant (''Piper nigrum''). The -az- infix added to "piperazine" refers to the extra nitrogen atom, compared to piperidine. It is important to note, however, that piperazines are ''not'' derived from plants in the '' Piper'' genus. Chemistry Piperazine is freely soluble in water and ethylene glycol, but insoluble in diethyl ether. It is a weak base with two pKb of 5.35 and 9.73 at 25 °C.; the pH of a 10% aqueous solution of piperazine is 10.8–11.8. Pi ...
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PFPP
''para''-Fluorophenylpiperazine (pFPP, 4-FPP, 4-Fluorophenylpiperazine; Fluoperazine, Flipiperazine) 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. pFPP has been found ''in vitro'' to act mainly as a 5-HT1A receptor agonist, with some additional affinity for the 5-HT2A and 5-HT2C receptors. It has also been shown to inhibit the reuptake of serotonin and norepinephrine, and to possibly induce their release. pFPP was originally discovered as a metabolite of the hypnotic 5-HT2A and α1-adrenergic receptor antagonist niaprazine 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 ...
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3-Methylbenzylpiperazine
3-Methylbenzylpiperazine (3-Me-BZP) is a stimulant drug which is a derivative of benzylpiperazine. It has been sold as a designer drug, first being identified in Sweden in February 2012. See also * Methylbenzylpiperazine * Substituted piperazine 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. List of substituted piperazines Benzylpiperazines File:Benzylpiperazine.svg, 1- ... References {{DEFAULTSORT:Methylbenzylpiperazine, 3- Piperazines Stimulants Designer drugs Norepinephrine-dopamine releasing agents ...
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Piberaline
Piberaline (EGYT-475; Trelibet) is a psychoactive drug and member of the piperazine chemical class which was developed in the 1980s. It has stimulant and antidepressant effects which are thought to be due largely to its active metabolite benzylpiperazine. It was researched to a limited extent in Hungary and Spain, but was not widely accepted and does not seem to be in current use, although a closely related drug befuraline with similar effects has been slightly more successful. Synthesis 2-Chloropyridine, carbon monoxide & BZP reacted together. Or from picolinic acid & BZP. See also * Substituted piperazine 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. List of substituted piperazines Benzylpiperazines File:Benzylpiperazine.svg, 1- ... * Befuraline * Fipexide References Piperazines Carboxamides 2-Pyridyl compounds Serotonin-norepinephrine-dop ...
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1-Benzylpiperazine
Benzylpiperazine (BZP) is a recreational drug with euphoriant and stimulant properties. The effects produced by BZP are comparable to those produced by amphetamine. Adverse effects have been reported following its use including acute psychosis, renal toxicity and seizures. Deaths from piperazine derivatives are extremely rare, but there has been at least one death apparently due to BZP alone. Its sale is banned in several countries, including Australia, Canada, New Zealand, the United States, the Republic of Ireland, the United Kingdom, Bulgaria, Romania and other parts of Europe. History Development history BZP was first synthesized by Burroughs Wellcome & Company in 1944. It is often claimed that it was originally synthesized as a potential antihelminthic (anti-parasitic) agent for use in farm animals, but its synthesis is thought to pre-date their interest in piperazines as anthelmintics. Even so, the majority of the early work with the piperazines were investigations i ...
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1-Methyl-4-benzylpiperazine
Methylbenzylpiperazine (1-methyl-4-benzylpiperazine, MBZP) 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. The effects of MBZP are very similar to those of benzylpiperazine (BZP), but the stimulant effect is slightly weaker and it seems to have less of a tendency to cause negative side effects such as headaches and nausea. 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 200 ...
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1,4-Dibenzylpiperazine
Dibenzylpiperazine (DBZP) is a piperazine derivative often found as an impurity in the recreational stimulant drug benzylpiperazine (BZP). Presence of DBZP is a marker for low quality or badly made BZP. It can be made as a reaction byproduct during BZP synthesis, either because the reaction has been run at too high a temperature, or because an excess of benzyl chloride has been used. Pharmacology and effects It is not known to have any stimulant effects in its own right, although this has not been tested. Toxicity The toxicity of DBZP is unknown. Legal status China As of October 2015 DBZP is a controlled substance in China. United States DBZP is not scheduled as a controlled substance at the federal level in the United States. It is possible that it could be considered an analog BZP, in which case, sales or possession intended for human consumption could be prosecuted under the Federal Analog Act. Florida DBZP is a Schedule I controlled substance in the state of Florida mak ...
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3,4-Methylenedioxy-1-benzylpiperazine
1-(3,4-Methylenedioxybenzyl)piperazine (MDBZP, piperonylpiperazine) is a chemical compound of the piperazine chemical class related to benzylpiperazine (BZP). MDBZP has been sold as a designer drug and has even been found as an ingredient in street Ecstasy pills. See also * 3,4-Methylenedioxy-''N''-methylamphetamine (MDMA) * Substituted piperazine 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. List of substituted piperazines Benzylpiperazines File:Benzylpiperazine.svg, 1- ... References External links * Benzodioxoles Designer drugs Piperazines {{nervous-system-drug-stub ...
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4-Bromo-2,5-dimethoxy-1-benzylpiperazine
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). Chemistry 2C-B-BZP contains a benzylpiperazine base as well as the ring-substitution pattern of the psychedelic phenethylamine 2C-B. 2C-B-BZP is not a phenethylamine itself and does not produce psychedelic effects, as the binding groups are in the wrong position to activate the 5-HT2A receptor, while the phenylpiperazine homologue 2C-B-PP substitutes for DOM in DOM-trained rats with around 1/10th the potency of DOM, but does not substitute for TFMPP. Effects 2C-B-BZP produces stimulant effects which last 3–6 hours. It is also said by several sources to increase the effects of other compounds when combined . Side effects include headaches and nausea, similar to those of other recreationally-used piperazine derivatives. Lega ...
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Methoxypiperamide
Methoxypiperamide (also known as MeOP and MEXP) is a psychoactive drug of the piperazine class that has been sold online as a designer drug. It is the 4-methoxy-α-keto analog of methylbenzylpiperazine. Very little data exists about the pharmacology and toxicity of methoxypiperamide; however, the US state of Vermont classifies it as a hallucinogen. Legal status Methoxypiperamide is a controlled substance in Vermont as of January 2016, and also in Hungary. See also * Substituted piperazine 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. List of substituted piperazines Benzylpiperazines File:Benzylpiperazine.svg, 1- ... * Sunifiram References Designer drugs Piperazines Amides Methoxy compounds {{psychoactive-stub ...
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Befuraline
Befuraline (DIV-154) is a psychoactive drug and member of the piperazine chemical class which was developed in Germany in the 1970s. Befuraline has stimulant and antidepressant effects and has seen some use in Germany and France, although it has never become widely used. Befuraline's active metabolite benzylpiperazine is likely to contribute to its effects. Synthesis A one-step coupling between coumarilic acid (benzofuran-2-carboxylic acid) 96-41-3(1) and benzylpiperazine (BzP) (2) gives an amide, and hence ''Befuraline'' (3). The conditions are Schotten-Baumann amidation. See also * Substituted piperazine * Fipexide * Piberaline Piberaline (EGYT-475; Trelibet) is a psychoactive drug and member of the piperazine chemical class which was developed in the 1980s. It has stimulant and antidepressant effects which are thought to be due largely to its active metabolite benzylp ... References Anthelmintics Piperazines Benzofuran-2-carboxamides Serotonin-norepinephrine- ...
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Fipexide
Fipexide (Attentil, Vigilor) is a psychoactive drug of the piperazine chemical class which was developed in Italy in 1983. It was used as a nootropic drug in Italy and France, mainly for the treatment of senile dementia, but is no longer in common use due to the occurrence of rare adverse drug reactions including fever and hepatitis. Fipexide is similar in action to other nootropic drugs such as piracetam and has a few similarities in chemical structure to centrophenoxine. Chemically, it is an amide union of parachlorophenoxyacetate and methylenedioxybenzylpiperazine (MDBZP), and has been shown to metabolize to the latter, which plays a significant role in its effects. Synthesis PTC alkylation of piperazine (1) with 2 equivalents of piperonyl chloride 5054-53-9(2) in the presence of cetrimonium bromide gives 1,4-bis-piperonylpiperazine 5436-41-4(3). Base catalyzed treatment with 4-Chlorophenoxyacetic acid (4) displaces one of the piperonyl groups to give fipexide (5). See a ...
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