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Benzylpiperazine

Benzylpiperazine (BZP), also known as 1-benzylpiperazine, is a substance often used as a recreational drug and is known to have euphoriant and stimulant properties. Several studies conducted between 2000 and 2011 found that the effects of BZP are similar to amphetamine, although BZP's dosage is roughly 10 times higher by weight.

Use and effects
The effects of BZP are largely similar to amphetamines, with one study finding that former amphetamine addicts were unable to distinguish between dextroamphetamine and BZP administered intravenously. Subjective effects Upon ingestion of between 50 mg and 200 mg of BZP, the user may experience any or all of the following: Initial effects: • Feelings of euphoria, wonder, amazement, well-being, energy and elation • Rapid mood elevation • Enhanced sociability • Enhanced appreciation of music • Increased desire to move, also slight increase in stereotypy • Skin tingling • Decreased appetite • Repetitive thought patterns • Actual and perceived changes in body temperature • Mild jaw clenching/bruxismIncreased heart rateDilation of pupils (see photo) • NauseaFlushing • Mild xerostomia (dry mouth) • Slight urinary incontinence, often described as "leaking" a small amount of urine after urinating (not due to loss of bladder control) Later effects: • Mild headache • Nausea • Hangover-like symptoms (common with high doses) • FatigueIndigestion (similar to acid indigestion/heartburn) • Increased hunger (and sometimes thirst) • InsomniaConfusion • Depression (particularly with frequent/heavy use) ==Adverse effects==
Adverse effects
Tolerance Research into BZP's toleranceis sparse. The more severe toxic effects include psychosis or adverse psychiatric events, renal toxicity, and seizure. Risk of fatality Ingestion of piperazine derivatives alone rarely causes death. In another case in Zürich in 2001, a 23-year-old who had taken BZP and MDMA died from a massive cerebral edema 57 hours after hospital admission. Addictive effects BZP has not been found to be physically addictive in humans. Studies undertaken on animals have indicated that BZP can substitute for methamphetamine in addicted rats, although it is one-tenth as potent and produces correspondingly weaker addictive effects. ==Pharmacology==
Pharmacology
Pharmacodynamics BZP has been shown to have a mixed mechanism of action, acting on the serotonergic and dopaminergic receptor systems in a similar fashion to MDMA. BZP has amphetamine-like actions on the serotonin reuptake transporter, which increase serotonin concentrations in the extracellular fluids surrounding the cell and thereby increasing activation of the surrounding serotonin receptors. BZP has a lower potency effect on the noradrenaline reuptake transporter and the dopamine reuptake transporter. Another study lists 1-Benzylpiperazine (BZP)'s Release DAT, NET, and SERT EC50s (i.e. a measure of potency for the release of neurotransmitters via BZP's affinity for the dopamine, norepinephrine, and serotonin transporters respectively--whereby those transporter are induced to shuttle neurotransmitters out of neurons and deposit them in the synaptic gap) as 175, 62, and 6050; for comparison, the values listed for d-amphetamine (25, 7, and 1765) and d-methamphetamine (25, 12, and 736) show a similar DAT:NET affinity ratio as well as minor SERT activity which suggests BZP possesses similar activity to the two aforementioned drugs (when dosed ~7x higher due to lower potency) rather than serotonergic substituted amphetamines like MDMA. BZP also acts as a non-selective serotonin receptor agonist on a wide variety of serotonin receptors. However, in spite of the reported hallucinogenic effects of BZP at high doses, the drug does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. Pharmacokinetics The pharmacokinetics of BZP have been studied. ==Chemistry==
Chemistry
BZP is a piperazine derivative which comes as either the hydrochloride salt or a free base. The hydrochloride salt is a white solid while the base form is a slightly yellowish-green liquid. BZP base is corrosive and causes burns. Derivatives • Pharmaceuticals • Befuraline – Antidepressant • Bifeprunox – Antipsychotic • Buclizine – Antihistamine • Chlorbenzoxamine – Gastrointestinal agent • Fipexide – Nootropic • Imatinib – Anticancer agent • Meclozine – Antihistamine • Piberaline – Antidepressant • Piribedil – Antiparkinsonian agent • Trimetazidine – Antianginal • Vesnarinone – Cardiotonic • Designer drugs • 3-Methylbenzylpiperazine4-Methyl-1-benzylpiperazine (MBZP) • 4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP) • 1,4-Dibenzylpiperazine (DBZP) • 3,4-Methylenedioxy-1-benzylpiperazine (MDBZP) Diphenylmethylpiperazines are also similar to benzylpiperazines. ==History==
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 predate their interest in piperazines as antihelminthics. It was discovered that BZP had side effects and was largely abandoned as a worm treatment. It next appears in the literature in the 1970s when it was investigated as a potential antidepressant medication, Recreational history In 1996, the United States Drug Enforcement Administration noted that it was being recreationally used in California. BZP, which is often mixed with TFMPP, has been claimed to be a safer alternative to other illicit street drugs. which has similar effects, and is sometimes marketed as "ecstasy", a colloquial term for MDMA. BZP has also been used and prohibited in horse racing and athletics. ==Society and culture==
Society and culture
Recreational sale BZP is often marketed ostensibly as a "dietary supplement" to avoid meeting stricter laws that apply to medicines and drugs, despite the fact that BZP has no dietary value. As of late 2005, the Misuse of Drugs Act ensured it can no longer be classified or marketed as a dietary supplement in New Zealand. Some retailers claim that BZP is a "natural" product, describing it as a "pepper extract" or "herbal high," when in fact the drug is entirely synthetic, Legal status BZP is banned in Australia, Austria, Canada, Denmark, Estonia, France, Germany, Greece, Ireland, Italy, Japan, Malta, Poland, Sweden and the United States. BZP is not controlled under any UN convention, so the compounds themselves are legal throughout most of the world, although in most countries their use is restricted to pharmaceutical manufacturing and recreational use is unknown. when BZP and piperazine analogs become illegal in the federal schedules, which are enacted by all Australian states and territories. Canada In Canada, Benzylpiperazine and salts of benzylpiperazine are classified as Schedule III controlled substances under the Controlled Drugs and Substances Act. European Union Benzylpiperazine was the subject of a European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) risk assessment to determine to determine how to control it throughout the European Union. The risk assessment came about as the result of a joint Europol – EMCDDA report which concluded that BZP needs to be looked at in more detail. The report was published in June 2007, and concluded that the use of BZP can lead to medical problems even if the long effects are still unknown. Taking this concession as a basis, the European Commission asked the Council to place BZP under control of the UN Convention on Psychotropic Substances. On 4 March 2008, the EU requested countries to place BZP under control within a year. Finland Scheduled in "government decree on narcotic substances, preparations and plants" and is hence illegal. New Zealand Based on the recommendation of the EACD, the New Zealand government passed legislation which placed BZP, along with other piperazine derivatives (TFMPP, mCPP, pFPP, MeOPP, and MBZP), into Class C of the Misuse of Drugs Act 1975. A ban was intended to come into effect in New Zealand on 18 December 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 was in effect until October 2008, at which point they became completely illegal. United Kingdom Piperazine and salts of piperazine are classified as Prescription Only Medicines in the UK. Any products containing salts of piperazine would be licensable under the Medicines Act and consequently anyone manufacturing and supplying it legally must hold the relevant licenses to do so. BZP is not a salt of piperazine, but mislabelling of BZP products as containing "piperazine blend" resulted in some prosecutions of suppliers in the UK by the Medicines and Healthcare Products Regulatory Agency, although none were successful. In May 2009, the Home Office announced plans to ban BZP, and launched a consultation on the proposal. In October 2009, it was announced that from 23 December 2009, BZP and related piperazines would be Class C drugs under the Misuse of Drugs Act. United States The drug was federally classified as a Schedule I controlled substance in the United States in 2002, when in fact BZP is ten times less potent than dexamphetamine. It is also illegal at the state level in Florida, Oklahoma, Vermont, and Virginia. ==See also==
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