Benzylpiperazine
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| 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, it is legal in other countries such as New Zealand.
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History
BZP was originally synthesized in 1944 as a potential anthelmintic — that is, an 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
Bzp_brands.jpg
A selection of products containing BZP. Legally available throughout New Zealand.
Where legal, BZP is often produced in small specialist laboratories. The raw materials can be purchased in bulk 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 - the final product can sell for around 80 times the cost of the raw ingredients.
BZP is often marketed ostensibly as a "dietary supplement" to avoid meeting stricter laws that apply to medicines and drugs. This is despite the fact that BZP has no dietary value.
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, not occurring naturally in any plant.
Effects
Eye_bzp.jpg
Significantly dilatated pupil after taking BZP.
The effects of BZP are allegedly similar to, although somewhat subtler than, the effects of ecstasy and methamphetamine. Users report arousal, euphoria and a general feeling of wellbeing. The perception of certain sensations — such as taste, colour or music — may be notably enhanced.
However there appear to be significant side effects associated with BZP use. BZP reportedly produces a severe hangover after the drug effect wears off. Other side effects include dilated pupils, dryness of the mouth, and problems with urine retention.
Only one death has ever been officially recorded of someone using BZP (Bamelli 2001). In this case, a young woman had consumed a quantity of BZP as well as ecstasy. She subsequently died of cerebral oedema due to hyponatremia resulting from water intoxication. Based on prior case reports, it is very likely that the ecstasy was the sole causative agent; it is dubious whether the BZP had any role in her death.
Mechanism
BZP has been shown to have a mixed mechanism of action, acting primarily ot the serotonergic system. BZP probably has amphetamine like actions on the serotonin reuptake transporter, which means it causes the transporter to work in reverse, pumping serotonin out of the cell and into the extracellular fluid surrounding the cell. This means that there is an increased level of serotonin to act on surroudning 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 made illegal in the USA 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. 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) (Adobe PDF format)
- New Zealand student magazine (Critic) on effects of various formulations.
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. [1]
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