Benzylpiperazine
|
Benzylpiperazine chemical structure | |
| IUPAC name:
N-Benzylpiperazine | |
| CAS number 2759-28-6 |
ATC code ? |
| Chemical formula | C11H16N2 |
| Molecular weight | 176.26 |
| Bioavailability | ? |
| Metabolism | Primarily hydroxylation (hepatic?) |
| Elimination half-life | A few hours (estimate) |
| Excretion | Primarily urinary |
| Pregnancy category | Uncategorised: should be avoided |
| Legal status | Varies; DEA Schedule 1 drug; legal in some countries |
| Routes of administration | Oral |
Benzylpiperazine (BZP) is a recreational drug with euphoric, stimulant effects. It is banned in many countries, including the United States and in parts of Australia and Europe. However, its legal status is less restrictive in some other countries such as New Zealand (see below).
History
BZP was originally synthesized in 1944 as a potential anthelmintic (anti-parasitic) agent. (Many piperazines have anti-parasitic effects; they paralyse the parasites and allow them to be flushed out of the host body.) However, it turned out that BZP was fairly ineffective and had significant side effects. It was largely abandoned, although a few studies examined its stimulant effects in the 1970s and 1980s.
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.
Production
Where legal, BZP is 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 (as high as 80 times the cost of 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. It is worth noting however that as of late 2005 it can no longer be classified or marketed as a dietary supplement in New Zealand[1].
Producers frequently claim that BZP is a "natural" product, describing it as a "pepper extract" or "herbal high". In fact, the drug is entirely synthetic, and does not occur naturally.
Effects
The effects of BZP are largely similar to dextroamphetamine1. 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.
A recent study has shown that mixtures of BZP with other piperazine drugs such as TFMPP share certain pharmacology traits with MDMA2.
As with most sympathomimetic stimulants there appears to be significant side effects associated with BZP use. BZP reportedly produces a severe hangover after the drug effect wears off, however some manufacturers in New Zealand have started including recovery pills which contain 5htp to help with these hangovers. Other side effects include dilated pupils, dryness of the mouth, reduced appetite, teeth clenching and problems with urine retention.
One death has been officially recorded in connection with the use of BZP. (Bamelli 2001) In this case, a young woman had consumed a quantity of BZP as well as MDMA. She subsequently died of cerebral edema due to hyponatremia resulting from water intoxication. It is uncertain whether the BZP had any role in her death.
A recent study in New Zealand implicated BZP as a cause of a variety of adverse effects, including life threatening seizures in neurologically normal subjects (Gee et al 2005). Another problem discovered in the studies showed that actual doses in the pills varied considerably to what was stated on the packet.
1. One study found that former amphetamine addicts were unable to distinguish between d-amphetamine and BZP administered intravenously. (Comparison of the effects of dexamphetamine and 1-benzylpiperazine in former addicts. Eur J Clin Pharmacol. 1973 Oct;6(3):170-6.)
2. N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy'). Neuropsychopharmacology. 2005 Mar;30(3):550-60.
Subjective Effects
Upon ingestion of between 50mg-200mg:
Coming up:
- Changes in body temperature
- Nausea
- Flushing
- Rapid mood lift
- Increased heart rate
- Dilation of pupils
- Decreased appetite
- "Rushing" sensation
- Mild to moderate synesthesia
- Skin tingling
- Feelings of euphoria, wonder, amazement, elation
- Increased desire to move
- Sensory stimulation (audio, visual)
- A sense of connectedness with other people (when combined with TFMPP)
Coming down
- Mild headache (hangover like symptoms)
- Fatigue
- Insomnia
- Confusion
- Mild memory loss
- Gradual reduction of effects in the "coming up" phase
Mechanism of action
BZP has been shown to have a mixed mechanism of action, acting on the serotonergic and dopaminergic receptor systems. BZP probably 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 also has a lower potency effect noradrenaline reuptake transporter and the dopamine reuptake transporter. BZP also has a high affinity action at the alpha2-adrenoreceptor. BZP is an antagonist at the receptor, like yohimbine, which inhibits negative feedback, causing an increase in released noradrenaline. BZP also has very weak partial agonist or antagonist effects at the 5-HT2B serotonin receptor, a receptor expressed very densly on the gut, which may explain some of BZPs peripheral side effects.
Legal issues
The drug was classified as a Schedule I controlled substance in the United States in 2002. It is banned in the more conservative Australian states.
In some other places (such as New Zealand), BZP is legal, and used as a harm-reduction measure, however this legislation is under review and it may be classed as a "schedule 4" drug[2]. BZP is also currently legal in England and Wales. It is not a classified drug under the Misuse of Drugs Act 1971. The drug is relatively safe, and enables users to receive a known amount of a drug in a safe environment.
See also
External links
- BZP information from the US DEA.
- New Zealand Expert Advisory Committee on Drugs Advice to the Minister on Benzylpiperazine (BZP) (PDF file)
- New Zealand student magazine (Critic) on effects of various formulations.
- Article on NZ study of BZP side-effects.
References
- Balmelli C, Kupferschmidt H, Rentsch K, Schneemann M. Fatal brain edema after ingestion of ecstasy and benzylpiperazine. Dtsch Med Wochenschr. 2001 Jul 13;126(28-29):809-11. [3]
- Gee P, Richardson S, Woltersdorf W, Moore G. Toxic effects of BZP-based herbal party pills in humans: a prospective study in Christchurch, New Zealand. New Zealand Medical Journal. 2005 Dec 16;118(1227):U1784. [4]