2C-B-BZP

Last updated
2C-B-BZP
2C-B-BZP.svg
2cbBZP3d.png
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
Identifiers
  • 1-[(4-Bromo-2,5-dimethoxyphenyl)methyl]piperazine
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H19BrN2O2
Molar mass 315.211 g·mol−1
3D model (JSmol)
  • C1(=CC(=C(C=C1CN2CCNCC2)OC)Br)OC
  • InChI=1S/C13H19BrN2O2/c1-17-12-8-11(14)13(18-2)7-10(12)9-16-5-3-15-4-6-16/h7-8,15H,3-6,9H2,1-2H3 Yes check.svgY
  • Key:OHXVYXBOJDDYJS-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP) is a psychoactive drug and research chemical of the piperazine chemical class which has been sold as a "designer drug". [1] [2] It produces stimulant effects similar to those of benzylpiperazine (BZP).

Contents

Chemistry

2C-B-BZP contains a benzylpiperazine base as well as the ring-substitution pattern of the psychedelic phenethylamine 2C-B. 2C-B-BZP is not a phenethylamine itself and does not produce psychedelic effects, as the binding groups are in the wrong position to activate the 5-HT2A receptor, while the phenylpiperazine homologue 2C-B-PP substitutes for DOM in DOM-trained rats with around one-tenth the potency of DOM, but does not substitute for TFMPP. [3] :867–868

Effects

2C-B-BZP produces stimulant effects which last 3–6 hours. It is also said by several sources to increase the effects of other compounds when combined [ citation needed ]. Side effects include headaches and nausea, similar to those of other recreationally-used piperazine derivatives.

Legality

2C-B-BZP is unscheduled and uncontrolled in the United States, but possession and sale of 2C-B-BZP could possibly be prosecuted under the Federal Analog Act because of its structural similarities to benzylpiperazine. 2C-B-BZP is illegal to possess, use or sell in Japan where it used to be sold in local smartshops.

See also

Related Research Articles

<span class="mw-page-title-main">2C-B</span> Chemical compound

2C-B (4-bromo-2,5-dimethoxyphenethylamine) is a synthetic psychedelic drug of the 2C family, mainly used as a recreational drug. The substance was first synthesized by Alexander Shulgin in 1974, and gained an initial reputation for potential psychotherapeutic use, but its use has been limited to mainly recreational use. To date, there is limited scientific information regarding the drug's pharmacokinetics and pharmacological effects in humans. The existing studies primarily classify 2C-B as a stimulant, and hallucinogen, and less commonly as an entactogen, and empathogen.

<span class="mw-page-title-main">2C-T-7</span> Psychedelic phenthylamine drug

2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10–30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours. Up until Operation Web Tryp and three deaths, two of which involved the use of other drugs in addition to 2C-T-7, and one which involved an excessive insufflated dose, 2C-T-7 was sold commercially in Dutch and Japanese smartshops and online. It is known on the streets as Blue Mystic or 7th Heaven. There has been little real research done on this chemical other than Shulgin's comments in PiHKAL and a few small animal studies mostly aimed at detecting metabolites.

<span class="mw-page-title-main">2C-T-2</span> Chemical compound

2C-T-2 is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds. The drug has structural and pharmacodynamic properties similar to those of 2C-T-7.

A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Designer drugs include psychoactive substances that have been designated by the European Union as new psychoactive substances (NPS) as well as analogs of performance-enhancing drugs such as designer steroids. Some of these were originally synthesized by academic or industrial researchers in an effort to discover more potent derivatives with fewer side effects and shorter duration and were later co-opted for recreational use. Other designer drugs were prepared for the first time in clandestine laboratories. Because the efficacy and safety of these substances have not been thoroughly evaluated in animal and human trials, the use of some of these drugs may result in unexpected side effects.

<span class="mw-page-title-main">Benzylpiperazine</span> Recreational drug

Benzylpiperazine (BZP) 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.

<span class="mw-page-title-main">Trifluoromethylphenylpiperazine</span> Chemical compound

3-Trifluoromethylphenylpiperazine (TFMPP) is a recreational drug of the phenylpiperazine chemical class and is a substituted piperazine. Usually in combination with benzylpiperazine (BZP) and other analogues, it is sold as an alternative to the illicit drug MDMA ("Ecstasy").

<span class="mw-page-title-main">2C-TFM</span> Psychedelic phenethylamine drug

2C-TFM is a psychedelic phenethylamine of the 2C family. It was first synthesized in the laboratory of David E. Nichols. It has also been called 2C-CF3, a name derived from the Para-trifluoromethyl group it contains.

<span class="mw-page-title-main">2C-B-FLY</span> Psychedelic designer drug

2C-B-FLY is a psychedelic phenethylamine and designer drug of the 2C family. It was first synthesized in 1996 by Aaron Monte, Professor of Chemistry at UW-La Crosse.

<span class="mw-page-title-main">Party pills</span> Type of recreational drugs

Party pills, also known as "herbal highs", "pep pills" "dance pills" and "natural power", is a colloquialism for a type of recreational drug whose main ingredient was originally benzylpiperazine (BZP), but has expanded to a wide range of compounds with a variety of effects. BZP is banned in several countries, including the USA, Republic of Ireland, Australia and New Zealand, but is available on a more or less restricted basis in many jurisdictions. A range of other piperazine derivatives have also been sold as ingredients in party pills, and many of these branded "proprietary blends" have subsequently been sold in countries around the world.

<i>para</i>-Methoxyphenylpiperazine Chemical compound

para-Methoxyphenylpiperazine is a piperazine derivative with stimulant effects which has been sold as an ingredient in "Party pills", initially in New Zealand and subsequently in other countries around the world.

<span class="mw-page-title-main">Piberaline</span> Chemical compound

Piberaline is a psychoactive drug and member of the piperazine chemical class which was developed in the 1980s. It has stimulant and antidepressant effects which are thought to be due largely to its active metabolite benzylpiperazine. It was researched to a limited extent in Hungary and Spain, but was not widely accepted and does not seem to be in current use, although a closely related drug befuraline with similar effects has been slightly more successful.

<span class="mw-page-title-main">Methylbenzylpiperazine</span> Chemical compound

Methylbenzylpiperazine is a stimulant drug which is a derivative of benzylpiperazine. MBZP has been sold as an ingredient in legal recreational drugs known as "party pills", initially in New Zealand and subsequently in other countries around the world.

<span class="mw-page-title-main">25B-NBOMe</span> Chemical compound

25B-NBOMe is a derivative of the phenethylamine psychedelic 2C-B, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent full agonist for the 5HT2A receptor. Anecdotal reports from users suggest 25B-NBOMe to be an active hallucinogen at a dose of as little as 250–500 µg, making it a similar potency to other phenethylamine derived hallucinogens such as Bromo-DragonFLY. Duration of effects lasts about 12–16 hours, although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses. Recently, Custodio et al (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.

βk-2C-B Chemical compound

βk-2C-B is a novel psychedelic substance. It is the beta (β) ketone structural analogue of 2C-B, a psychedelic drug of the 2C family. It is used as a recreational drug, usually taken orally. βk-2C-B is a controlled substance in Canada, Germany, Switzerland, and the United Kingdom.

<span class="mw-page-title-main">25B-NBOH</span> Chemical compound

25B-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-B which has been sold as a designer drug. It acts as a potent serotonin receptor agonist with similar affinity to the better-known compound 25B-NBOMe at 5-HT2A and 5-HT2C receptors with pKis values of 8.3 and 9.4, respectively.

<span class="mw-page-title-main">25B-NBF</span> Chemical compound

25B-NBF is a derivative of the phenethylamine hallucinogen 2C-B, which acts as a highly potent partial agonist for the human 5-HT2A receptor.

Substituted piperazines are a class of chemical compounds based on a piperazine core. Some are used as recreational drugs and some are used in scientific research.

<span class="mw-page-title-main">2C-B-PP</span> Chemical compound

2,5-dimethoxy-4-bromophenylpiperazine (2C-B-PP) is a drug of the phenylpiperazine class. It acts as an agonist at serotonin receptors, and in studies on rats substituted for the psychedelic amphetamine derivative DOM with around 1/10 the potency but similar rates of stimulus-appropriate responding at the highest dose.

<span class="mw-page-title-main">4C-B</span> Chemical compound

4C-B is a lesser-known psychedelic drug which is related to 2C-B and DOB. It is a reasonably potent 5-HT2A receptor partial agonist with a Ki of 7.6nM, but has relatively low efficacy. It is briefly mentioned in Alexander Shulgin's book PiHKAL but was never tested by him, however it has subsequently been tested by other researchers and was found to be active in a dose range of 50-80mg with a duration of around 8 hours, though with generally milder effects than 2C-B or DOB.

References

  1. Westphal F, Junge T, Girreser U, Stobbe S, Pérez SB (May 2009). "Structure elucidation of a new designer benzylpiperazine: 4-bromo-2,5-dimethoxybenzylpiperazine". Forensic Science International. 187 (1–3): 87–96. doi:10.1016/j.forsciint.2009.03.003. PMID   19345524.
  2. Peters FT, Martinez-Ramirez JA (October 2010). "Analytical toxicology of emerging drugs of abuse". Therapeutic Drug Monitoring. 32 (5): 532–539. doi:10.1097/FTD.0b013e3181f33411. PMID   20814349. S2CID   8009246.
  3. Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN   978-3-03788-700-4.