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20-September-2008 09:55:55 - Benzylpiperazine Benzylpiperazine Systematic IUPAC name 1-benzylpiperazine Identifiers CAS number 2759-28-6 ATC code ? PubChem 75994 Chemical data Formula C11H16N2 Mol. mass 176.258 g/mol SMILES eMolecules PubChem Pharmacokinetic data Bioavailability ? Metabolism hepatic Half life ? Excretion renal Therapeutic considerations Pregnancy cat. ? Legal status DEA Schedule 1 drug; legal in some countries Routes oral, intravenous, insufflation Benzylpiperazine with trade names such as A2, Frenzy and Nemesis,1 commonly referred to as BZP is a recreational drug with euphoric, stimulant properties. Its dopamine and serotonin agonist mechanism of action is believed to be similar to MDMA and 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. It does not appear to be very addictive and no deaths have been reported following a sole ingestion of BZP, although there have been at least two deaths from the combination of BZP and MDMA. Its sale is banned in a few countries, including the United States, Australia, New Zealand and in parts of Europe.2 However, its legal status is currently less restrictive in some other countries such as Ireland and Canada, although investigations and regulations are pending under European Union laws. Contents 1 History 1.1 Development history 1.2 Recreational history 2 Production and distribution 3 Pharmacodynamics 4 Effects 4.1 Subjective effects 4.2 Tolerance 4.3 Toxic effects 4.3.1 Christchurch study 4.3.2 Aborted Medical Research Institute of New Zealand Study 4.4 Attributed deaths 4.5 Addictive effects 5 Legal issues 6 See also 7 Footnotes 8 External links History Development history It is often claimed that BZP was originally synthesized as a potential antihelminthic anti-parasitic agent for use in farm animals.3 However, there are some references to BZP in medical literature that predate interest in piperazines as anthelmintics. Even so, the majority of the early work with the piperazines were investigations into their potential use as anthelmintics with the earliest clinical trials in the literature relating to piperazine being articles in the British Medical Journal in the 1950s.45 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, but rejected when research reported that BZP had amphetamine-like effects and was liable to abuse. The study suggested that BZP should be placed under statutory control similar to those regulating the use of amphetamine.6 Recreational history In the early 1990s, the United States Drug Enforcement Administration noted the drug was being used recreationally in California. It also reported that BZP was being used as an adulterant in illicit drugs. Not long after, there was an explosion in the drug's use worldwide - a situation which was soon followed by legislative control in many countries. Since 1999, benzylpiperazine use grew sharply in New Zealand, where there was initially a complete lack of regulation. The New Zealand government attempted to ban the product as of December 18, 2007, but the necessary second reading of the bill did not happen in time for the law to be passed.78 It was so widely used that an estimated 5 million pills were sold in New Zealand in 2007.9 Piperazine-based stimulants began to appear in Europe in 200010 but remained virtually unavailable in the rest of the world until recently. In early 2006, pills containing the active ingredients BZP and TFMPP began to appear in the city of Vancouver, Canada, where they first gained popularity with late night party-goers as a safer alternative to many of the illicit street drugs commonly available there. The very first BZP based party-pills to be manufactured and marketed in Canada were sold under the brand name Lovely and are now commonly referred to as Lovelies within the party scene. Recentlywhen? piperazine based party-pill formulations have become widely available nationwide which has caused concern with local authoritieswho? and subsequently BZP has gained much media attention in 2008. Piperazines such as BZP and TFMPP are currentlywhen? under evaluation by Health Canada in order to determine whether or not party-pills pose a significant health risk to individuals. At this time no official decision has been made regarding these specific piperazines becoming restricted substances, or if they should be banned altogether in Canada. In the United States, it is still used as an adulterant in ecstasy mimic tablets.citation needed Production and distribution A selection of products containing BZP. A selection of products containing BZP. 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.11 In countries where its purchase is legal, BZP products are often produced in small specialist laboratories. The raw materials can be purchased from various chemical supply agencies and formed into tablets or capsules using relatively cheap production techniques. The resulting product can be marketed at extremely high markup, so end-user prices can be as high as 300 times the bulk cost of raw ingredients. 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.7 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,9 and has not been found to occur naturally.12 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.13 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.1415 BZP has a lower potency effect on the noradrenaline reuptake transporter and the dopamine reuptake transporter.13 BZP has a high affinity action at the alpha2-adrenoreceptor, it is an antagonist at the receptor, like yohimbine, which inhibits negative feedback, causing an increase in released noradrenaline.16 BZP also acts as a non-selective serotonin receptor agonist on a wide variety of serotonin receptors;14 binding to 5HT2A receptors may explain its mild hallucinogenic effects at high doses, while partial agonist or antagonist effects at the 5HT2B receptors may explain some of BZPs peripheral side effects, as this receptor is expressed very densely in the gut, and binding to 5HT3 receptors may explain the common side effect of headaches, as this receptor is known to be involved in the development of migraine headaches. There is still much that is not known about the pharmacokinetics of benzylpiperazine. Its metabolism is mainly through the enzymes CYP2D6 and COMT.9 Effects Typical pupil dilation Typical pupil dilation The effects of BZP are largely similar to amphetamines,17 with one study finding that former amphetamine addicts were unable to distinguish between dextroamphetamine and BZP administered intravenously.18 Users report alertness, euphoria and a general feeling of well being. The perception of certain sensations such as taste, colour or music may be subjectively enhanced. The average duration is longer than that of dextroamphetamine, typically lasting 4-6 hours with reports as long as 8 hours depending on the dose.19 A recent study has shown that mixtures of BZP with other piperazine drugs such as TFMPP share certain pharmacodynamic traits with MDMA.13 Subjective effects Upon ingestion of between 50 mg and 200 mg of BZP, the user may experience any or all of the following: Coming up:192021 Actual and perceived changes in body temperature Slight nausea Flushing Mild xerostomia dry mouth Rapid mood elevation Mild jaw clenching/bruxism Increased heart rate Enhanced sociability Repetitive thought patterns Dilation of pupils see photo Decreased appetite Slight urinary incontinence, often described as leaking a small amount of urine after urinating not due to loss of bladder control Rushing sensation19 Enhanced appreciation of music Skin tingling Feelings of euphoria, wonder, amazement, well-being, energy and elation Increased desire to move, also slight increase in stereotypy Coming down:20 Mild headache Nausea Hangover-like symptoms common with high doses Fatigue Increased hunger and sometimes thirst Insomnia Confusion Loss of appetite Tolerance Research into BZP's tolerance is sparse. Anecdotal evidence from online sources claim tolerance to the central action of BZP will develop quickly.16 Due to tiredness associated with the body's recovery from stimulants, such as BZP, it is uncommon for users to be able to sustain a week-long intake. Toxic effects An 'ecstasy' tablet - seized by law enforecement in the United States - containing BZP, methamphetamine, and caffeine An 'ecstasy' tablet - seized by law enforecement in the United States - containing BZP, methamphetamine, and caffeine As with most sympathomimetic stimulants there appear to be significant side effects associated with BZP use. BZP reportedly produces insomnia and a mild to severe hangover after the drug effect wears off,20 however, some manufacturers in New Zealand have started including recovery pills which contain 5-HTP and vitamins which allegedly ease these hangovers. The major side effects include dilated pupils, blurred vision, dryness of the mouth, extreme alertness, pruritus, confusion, agitation, tremor, extrapyramidal symptoms dystonia, akathisia, headache, dizziness, anxiety, insomnia, vomiting, chest pain, hallucinations, paresthesia, tachycardia, hypertension, palpitations, collapse, hyperventilation, sweating, hyperthermia, and problems with urine retention.20222324 The more severe toxic effects include psychosis,25 renal toxicity,12 respiratory failure,22 and seizure.2023 Christchurch study The majority of the toxic effects information came from a study conducted between 1 April 2005 to 1 September 2005. The study recorded all presentations associated with party pill use at the Emergency Department of Christchurch Hospital, New Zealand by recording them on a prospective data collection form. The aim was to study the patterns of human toxicity related to the use of benzylpiperazine-based 'party pills'. 61 patients presented on 80 occasions. Patients with mild to moderate toxicity experienced symptoms such as insomnia, anxiety, nausea, vomiting, palpitations, dystonia, and urinary retention. Significantly, fourteen toxic seizures were recorded with two patients suffering life-threatening toxicity with status epilepticus and severe respiratory and metabolic acidosis. It was concluded that BZP appears to induce toxic seizures in neurologically normal subjects.23 The results of this study and others like it2024 showed that BZP can cause unpredictable and serious toxicity in some individuals, but the data and dosage collection were reliant on self reporting by drug users, which may result in under-reporting, and there were complicating factors like the frequent presence of alcohol and other drugs.24 Aborted Medical Research Institute of New Zealand Study In 2007 STANZ commissioned an independent report into the MRINZ Study on BZP which was aborted and widely reported on by the media as proof of BZP harm, and relied on by the Expert Advisory Committee on Drugs EACD when they recommended to reclassify BZP to a class C restricted substance. This independent report on the study found major biases in the study including:26 That the term seizures was used to refer to anything from a small twitch to a grand seizure and that this was too broad. Further, there was a failure in some studies to explain if the seizures were due to withdrawal effects. That the MRINZ study was designed to look at driving performance under an intoxicating dose of BZP with or without alcohol rather than at the side effects of BZP and that the results should be used to inform the study's primary aim. That the side effects in the MRINZ study were were most likely heightened as participants endured at least six hours of fasting and the substance was taken when it is not normally taken. The Committee noted this might explain the discrepancy between the subjects' experience in the study and their prior experience with BZP. That one Committee member expressed the view that the Committee may have placed too much emphasis on the MRINZ study, in part because the aborting of the trial may have created an emotional overtone that influenced the Committee's decision. Attributed deaths According to party pill manufacturer Matt Bowden, over 20 million pills containing BZP have been consumed in New Zealand with no available record attributing deaths or lasting injuries to a single ingestion of BZP.27 Additionally, a retrospective study carried out at an Auckland emergency department found that BZP presentations only made a minor contribution to their overdose database with most cases not producing any significant toxicity.24 Several cases where BZP individually or combined with alcohol or other medicines or illicit drugs resulting in complications exist. One such example is the well publicised case of a combination of BZP and MDMA by a 23 year old from Greymouth, New Zealand. Ben Rodham, a DJ, ingested a combination of BZP and MDMA in February 2007, which nearly resulted in his death. Rodham was put into an induced coma in an effort to prevent him from dying. He later recovered.28 After many millions of doses consumed worldwide, two deaths have been officially recorded in correlation with the use of BZP, although no causal relationship has been proven.2930 In the first case in Zurich in 2001 a 23-year-old took two BZP tablets as well as ecstasy MDMA and drank more than 10 litres of water in a 15-hour period, subsequently dying of cerebral edema due to hyponatremia resulting from water intoxication.29 In the second case a 25 year old male ingested a large quantity of alcohol alongside BZP and MDMA.30 The cause of death of this individual has not been released. It is uncertain what role the BZP may have had in these deaths; death from hyponatremia is a well known consequence of drinking too much fluid after consuming MDMA,2331 it is likely that the additional hyponatremic effects from the BZP may have increased the hyponatremic effects from the MDMA, to the point that death resulted. Addictive effects One in every 45 2.2% last-year users of BZP in New Zealand is classed as dependent upon it, although 97.9% of users said that it would not be difficult to stop using legal party pills, and 45.2% of people who reported using both BZP and illegal drugs such as methamphetamine reported that they used BZP so that they did not have to use methamphetamine, which was perceived as more harmful.32 Still, most of the people who use BZP, even though they say it is quite easy to stop, do not want to, and continue to use the drug, feeling that it helps them to reach higher levels of mood, sociability, and energy.32 Studies undertaken on animals have indicated that BZP can substitute for methamphetamine in addicted rats, although it is ten times less potent and produces correspondingly weaker addictive effects.33 Legal issues The drug was classified as a Schedule I controlled substance in the United States in 2002,11 following a report by the DEA which incorrectly stated that BZP was 10 to 20 times more potent than amphetamine,34 when in fact BZP is ten times less potent than dexamphetamine.35 The DEA subsequently admitted this mistake, but nevertheless retained the Schedule 1 classification. BZP is banned in all Australian states. Victoria, the last state in which it was legal, changed its classification on September 1 2006.36 This is the date BZP and piperazine analogs become illegal in the federal schedules which are now enacted by all Australian states and territories. BZP is also a banned substance in Japan, along with TFMPP. Both Australia and Japan admit that their scheduling decisions were made primarily in response to the Schedule 1 classification given to BZP in the USA, although some instances of BZP use had been reported by law enforcement authorities in both countries. BZP is also banned in Greece, Italy, Malta, Denmark and Sweden.937 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 Act38 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 have resulted in some prosecutions of suppliers in the UK by the Medicines and Healthcare Products Regulatory Agency, though to this date there has not been a successful prosecution in the UK for the sale of BZP, so its legal status remains uncertain.39 Although sale is regulated, possession of BZP is still legal. For now, BZP and other analogous piperazines are legal and uncontrolled in many countries such as Canada and Ireland.37 They are 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.40 Benzylpiperazine is, however, to be the subject of a European Monitoring Centre for Drugs and Drug Addiction EMCDDA risk assessment, the results of which will determine what, if any, control will placed on BZP throughout the European Union. The risk assessment comes about as the result of a joint Europol - EMCDDA report which concluded that BZP needs to be looked at in more detail. The results were published in June 2007.41 The report 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 has decided to ask the Council to place BZP under control of the UN Convention on Psychotropic Substances.42 On 4 March 2008, the EU requested countries to place BZP under control within a year 43 and France complied on May 20th.44 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 18th 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 1st of April 2008. An amnesty for possession and usage of these drugs will remain until October 2008, at which point they will become completely illegal.45 See also Pharmacy and Pharmacology portal Benzedrine TFMPP mCPP MeOPP pFPP MBZP MDBZP 2C-B-BZP DBZP Party pills Piperazine Drug abuse Recreational drugs Footnotes ^ David McCandless 2005-12-13. Clubbers snap up new legal high. The Guardian. Retrieved on 2008-05-26. ^ Alexandra Topping 2007-06-18. Legal dance drug faces ban amid fears over side-effects. The Guardian. Retrieved on 2008-05-26. ^ Lay off the party pills. New Zealand Medical Association 2006-11-01. Retrieved on 2007-04-22. ^ White R, Standen O 1953. Piperazine in the treatment of threadworms in children; report on a clinical trial. British Medical Journal 2 4839: 755-7. PMID 13082101. ^ Standen O 1955. Activity of piperazine, in vitro, against Ascaris lumbricoides. British Medical Journal 2 4930: 20-2. PMID 14378628. ^ Campbell H, Cline W, Evans M, Lloyd J, Peck A 1973. Comparison of the effects of dexamphetamine and 1-benzylpiperazine in former addicts. Eur J Clin Pharmacol 6 3: 170-6. doi:10.1007/BF00558281. PMID 4586849. ^ a b Misuse of Drugs Amendment Act 2005. PDF. New Zealand Government 2005-06-17. Retrieved on 2007-04-22. ^ Michele McPherson 2007-12-12. Party Pill Ban Delayed. Bay of Plenty Times. Retrieved on 2007-12-31. ^ a b c d Gee P, Fountain J 2007. Party on? BZP party pills in New Zealand PDF. N Z Med J 120 1249: U2422. PMID 17308559. ^ de Boer D, Bosman I, Hidvégi E, Manzoni C, Benkö A, dos Reys L, Maes R 2001. Piperazine-like compounds: a new group of designer drugs-of-abuse on the European market. Forensic Sci Int 121 1-2: 47-56. doi:10.1016/S0379-07380100452-2. PMID 11516887. ^ a b Drugs and Chemicals of Concern: N-Benzylpiperazine. US DEA June 2006. Retrieved on 2007-04-22. ^ a b Alansari M, Hamilton D 2006. Nephrotoxicity of BZP-based herbal party pills: a New Zealand case report. N Z Med J 119 1233: U1959. PMID 16680176. ^ a b c Baumann M, Clark R, Budzynski A, Partilla J, Blough B, Rothman R 2004. Effects of Legal X piperazine analogs on dopamine and serotonin release in rat brain. Ann N Y Acad Sci 1025: 189-97. doi:10.1196/annals.1316.024. PMID 15542717. ^ a b Tekes K, Tóthfalusi L, Malomvölgyi B, Hermán F, Magyar K. Studies on the biochemical mode of action of EGYT-475, a new antidepressant. Pol J Pharmacol Pharm 39 2: 203-11. PMID 2448760. ^ Lyon R, Titeler M, McKenney J, Magee P, Glennon R 1986. Synthesis and evaluation of phenyl- and benzylpiperazines as potential serotonergic agents. J Med Chem 29 5: 630-4. doi:10.1021/jm00155a008. PMID 3701781. ^ a b Neuropharmacology of BZP. Erowid.org November 2003. Retrieved on 2007-04-22. ^ Fantegrossi W, Winger G, Woods J, Woolverton W, Coop A 2005. Reinforcing and discriminative stimulus effects of 1-benzylpiperazine and trifluoromethylphenylpiperazine in rhesus monkeys. Drug Alcohol Depend 77 2: 161-8. doi:10.1016/j.drugalcdep.2004.07.014. PMID 15664717. ^ Campbell H, Cline W, Evans M, Lloyd J, Peck A 1973. Comparison of the effects of dexamphetamine and 1-benzylpiperazine in former addicts. Eur J Clin Pharmacol 6 3: 170-6. doi:10.1007/BF00558281. PMID 4586849. ^ a b c BZP Experiences. drugs-forum.co.uk 2007-07-08. Retrieved on 2008-05-26. ^ a b c d e f Nicholson T 2006. Prevalence of use, epidemiology and toxicity of 'herbal party pills' among those presenting to the emergency department. Emergency medicine Australasia : EMA 18 2: 180-4. doi:10.1111/j.1742-6723.2006.00826.x. PMID 16669944. ^ Erowid experience vault: Lazer Light Loving BZP TFMPP. Erowid 2004-10-28. Retrieved on 2008-05-26. ^ a b Harnett MA 2007. Piperazine-Based Party Drugs: Case Series of 73 Poisonings abstract. Clin Toxicol Phila. 45 4: 373. doi:10.1080/15563650701284894. ^ a b c d Gee P, Richardson S, Woltersdorf W, Moore G 2005. Toxic effects of BZP-based herbal party pills in humans: a prospective study in Christchurch, New Zealand PDF. N Z Med J 118 1227: U1784. PMID 16372033. ^ a b c d Theron L, Jansen K, Miles J 2007. Benzylpiperizine-based party pills' impact on the Auckland City Hospital Emergency Department Overdose Database 2002-2004 compared with ecstasy MDMA or methylene dioxymethamphetamine, gamma hydroxybutyrate GHB, amphetamines, cocaine, and alcohol PDF. N Z Med J 120 1249: U2416. PMID 17308553. ^ Austin H, Monasterio E 2004. Acute psychosis following ingestion of 'Rapture'. Australasian psychiatry : bulletin of Royal Australian and New Zealand College of Psychiatrists 12 4: 406-8. PMID 15715818. ^ Dawson M, Wodak A. Report on the proposal to reclassify BZP. AccessUTS. Retrieved on 2008-05-26. ^ Bowden, Matt 2005-11-02. Call for BZP ban misses the point. STANZ. Retrieved on 2008-03-03. ^ Party On?. TV3 New Zealand 2007-04-09. Retrieved on 2007-04-14. ^ a b Balmelli C, Kupferschmidt H, Rentsch K, Schneemann M 2001. Fatal brain edema after ingestion of ecstasy and benzylpiperazine. Dtsch Med Wochenschr 126 28-29: 809-11. doi:10.1055/s-2001-15702. PMID 11499262. 11. ^ a b Carter, Bridget 2007-01-07. Coroner probes party pill link in New Year death. New Zealand Herald. Retrieved on 2007-04-22. ^ Hall A, Henry J 2006. Acute toxic effects of 'Ecstasy' MDMA and related compounds: overview of pathophysiology and clinical management. Br J Anaesth 96 6: 678-85. doi:10.1093/bja/ael078. PMID 16595612. ^ a b Wilkins C, Girling M, Sweetsur P, Huckle T, Huakau J. Legal party pill use in New Zealand: Prevalence of use, availability, health harms and 'gateway effects' of benzylpiperazine BZP and triflourophenylmethylpiperazine TFMPP PDF. Centre for Social and Health Outcomes Research and Evaluation SHORE. Retrieved on 2007-04-14. ^ Brennan K, Johnstone A, Fitzmaurice P, Lea R, Schenk S 2007. Chronic benzylpiperazine BZP exposure produces behavioral sensitization and cross-sensitization to methamphetamine MA. Drug Alcohol Depend 88 2-3: 204-13. doi:10.1016/j.drugalcdep.2006.10.016. PMID 17125936. ^ BZP: Fast Facts.. National Drug Intelligence Center September 2004. Retrieved on 2007-04-22. ^ DEA error on BZP potency PDF. Stargate International 2004-09-15. Retrieved on 2007-04-22. ^ Warning on buying banned drug over web. The Australian 2006-10-10. Retrieved on 2007-04-14. ^ a b Benzylpiperazine Legal Status. Erowid. Retrieved on 2008-05-26. ^ Sect. 8 of Medicines Act 1968 - Schedule 3, SI 3144 The Medicines for Human Use Marketing Authorisations Etc Regulations 1994 ^ Thousands of 'pep' pills seized in Middlesbrough. Medicines and Healthcare products Regulatory Agency 2006-08-17. Retrieved on 2007-04-14. ^ Benzylpiperazine Legal Status. Erowid.org 2002-11-17. Retrieved on 2007-04-22. ^ New drug under formal scrutiny: Council asks EMCDDA to assess risks of BZP PDF. European Monitoring Centre for Drugs and Drug Addiction 2007-03-23. Retrieved on 2007-04-14. ^ EUROPA 2007-07-17. New Commission proposal to strengthen control of synthetic drug BZP. Retrieved on 2008-02-01. ^ New drug BZP to be placed under control across the EU. European Monitoring Centre for Drugs and Drug Addiction 2008-03-03. Retrieved on 2008-05-26. ^ Classment comme stupefient de la BZP. ^ Misuse of Drugs Classification of BZP Amendment Bill. New Zealand Parliament 2007-08-20. Retrieved on 2008-05-26. External links Erowid BZP Vault New Scientist Story: Mind-altering drugs: does legal mean safe? v d e Stimulants Alkylamines Cyclopentamine Geranamine Isometheptene Octodrine Propylhexedrine Tuamine Alphapyrrolidinylalkiophenones α-PPP MDPPP MDPV MPBP MPHP MPPP MOPPP Pyrovalerone Cholinergics ABT-089 ABT-418 Anabasine Arecoline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine Rivanicline Tebanicline Varenicline Convulsants Bicuculline DMCM Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil Carphedon Modafinil Phenethylamines 4-Bromomethcathinone 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-Fluoromethcathinone 4-Methylmethcathinone 4-MTA Aletamine Amfepentorex Amphechloral Amphetamine Dextroamphetamine, Adderall Amphetaminil Benzphetamine Bupropion Cathinone Chlorphentermine Clenbuterol Clobenzorex Clortermine Diethylpropion Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Ephedrine Epinephrine Ethcathinone Ethylamphetamine Fenethylline Fenfluramine Fenproporex Fludorex Furfenorex Levomethamphetamine Lisdexamfetamine MDMA Mefenorex Methamphetamine Methcathinone Methoxyphedrine Methylone Octopamine Ortetamine Parahydroxyamphetamine PCA PIA PMA PMEA PMMA PPAP Phendimetrazine Phenmetrazine Phentermine Phenylephrine Phenylpropanolamine Propylamphetamine Pseudoephedrine Selegiline Synephrine Tiflorex Xylopropamine Phenylaminooxazoles 4-Methyl-aminorex Aminorex Clominorex Fenozolone Fluminorex Pemoline Thozalinone Piperazines 2C-B-BZP BZP GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine Piperidines 2-Benzylpiperidine Desoxypipradrol Diphemethoxidine Ethylphenidate HDMP-28 --Methyl-1-methyl-4β-2-naphthylpiperidine-3β-carboxylate Methylphenidate Dexmethylphenidate Nocaine Phacetoperane Pipradrol Tropanes 3α-Bis-4-fluorophenylmethoxytropane 3α-4-Chlorophenylphenylmethoxytropane 3-Pseudotropyl-4-fluorobenzoate Altropane IACFT Brasofensine CFT WIN 35,428 β-CIT RTI-55 Cocaethylene Cocaine β-CPPIT Dichloropane RTI-111 Difluoropine FE-β-CPPIT FP-β-CPPIT PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-121 IPCIT RTI-126 RTI-150 RTI-171 RTI-177 RTI-336 Tesofensine Troparil β-CPT, WIN 35,065-2 WF-23 WF-33 WF-60 Xanthines Aminophylline Caffeine Dimethazan Paraxanthine Theobromine Theophylline Others Amineptine Bemegride Benzydamine BPAP Bromantane BTQ Clofenciclan Cypenamine Cyprodenate Diclofensine Dimethocaine Diphenyl prolinol Ethamivan Fencamfamine Feprosidnine Gilutensin GYKI-52895 Hexacyclonate Indanorex Indatraline LR-5182 Mazindol Mesocarb Naphthylisopropylamine Nikethamide Nomifensine Phthalimidopropiophenone Prolintane Sibutramine Yohimbine Zylofuramine See also Sympathomimetic amines v d e Adrenergic antagonists α α1 selective Doxazosin · Prazosin · Alfuzosin · Terazosin · Indoramin · Urapidil · Trimazosin · Moxisylyte · 1A Tamsulosin, Silodosin α2 selective Atipamezole · Efaroxan · Idazoxan · Yohimbine · Benzylpiperazine · Rauwolscine · Mirtazapine Non-selective α reversible Phentolamine · irreversible Phenoxybenzamine β β1 selective cardioselective Atenolol · Acebutolol · Celiprolol · Betaxolol · Bisoprolol · Esmolol · Metoprolol · Nebivolol β2 selective Butaxamine · ICI 118551 β3 selective SR 59230A Non-selective β Alprenolol · Amosulalol · Metipranolol · Nadolol · Oxprenolol · Penbutolol · Pindolol · Propranolol · Tertatolol · Timolol · Tilisolol · Sotalol Mixed α1/β Carvedilol · Labetalol · Arotinolol Retrieved from http://en..org/wiki/Benzylpiperazine Categories: Serotonin receptor agonists | Stimulants | PiperazinesHidden categories: Vague or ambiguous time | Articles with specifically-marked weasel-worded phrases | All articles with statements | Articles with statements since August 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français Polski Suomi Svenska This page was last modified on 20 August 2008, at 23:15
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