Benzylpiperazine

Benzylpiperazine (BZP)N-Benzylpiperazine


IUPAC name:
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.Misuse of Drugs Amendment Act 2005

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 dextroamphetamineOne 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.) 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 MDMA."N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy')." Neuropsychopharmacology. 2005 Mar;30(3):550-60.

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.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. 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 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. Another problem discovered in the studies showed that actual doses in the pills varied considerably to what was stated on the packet.

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 densely 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. It is classed in New Zealand as a "Restricted Substance" by the Misuse of Drugs Act and restricted to those over 18 years.Misuse of Drugs Amendment Act 2005 Products containing BZP are marketed by manufacturers and sellers as a harm-reduction measure, however the legislation is currently under review pending the findings of a number of research projects into the effects of the drug. BZP is also currently legal in England and Wales. It is not a classified drug under the Misuse of Drugs Act 1971. Research into BZP is scarce. To date, the drug has been considered to be of low risk of harm to users, but more information is required.

References

External links

Drugs | Stimulants | Nitrogen heterocycles

BZP

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