Benzedrone

Last updated
Benzedrone
Benzedrone.svg
Clinical data
ATC code
  • none
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
  • (±)-1-(4-methylphenyl)-2-(benzylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C17H19NO
Molar mass 253.345 g·mol−1
3D model (JSmol)
  • c2ccccc2CNC(C)C(=O)c(cc1)ccc1C
  • InChI=1S/C17H19NO/c1-13-8-10-16(11-9-13)17(19)14(2)18-12-15-6-4-3-5-7-15/h3-11,14,18H,12H2,1-2H3
  • Key:KWHZRPBDEAQYDE-UHFFFAOYSA-N
   (verify)

Benzedrone (4-MBC) is a designer drug which has been found since 2010 as an ingredient in a number of "bath salt" mixes sold as recreational drugs. [1] [2] [3] [4] [5]

See also

Related Research Articles

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">Methylenedioxypyrovalerone</span> Chemical compound

Methylenedioxypyrovalerone (MDPV) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI). It was first developed in the 1960s by a team at Boehringer Ingelheim. Its activity at the dopamine transporter is six times stronger than at the norepinephrine transporter and it is virtually inactive at the serotonin transporter. MDPV remained an obscure stimulant until around 2004 when it was reportedly sold as a designer drug. In the USA, products containing MDPV and labeled as bath salts were sold as recreational drugs in gas stations, similar to the marketing for Spice and K2 as incense, until it was banned in 2011.

<i>alpha</i>-Pyrrolidinopentiophenone Chemical compound

α-Pyrrolidinopentiophenone is a synthetic stimulant of the cathinone class developed in the 1960s that has been sold as a designer drug. Colloquially, it is sometimes called flakka. α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.

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

Naphyrone, also known as O-2482 and naphthylpyrovalerone, is a substituted cathinone drug derived from pyrovalerone that acts as a triple reuptake inhibitor, producing stimulant effects and has been reported as a novel designer drug. No safety or toxicity data is available on the drug.

<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.

<span class="mw-page-title-main">Eutylone</span> Designer drug of the cathinone class

Eutylone is a stimulant and empathogenic compound developed in the 1960s, which is classified as a designer drug. It was first reported to the EMCDDA in 2014 and became widespread internationally in 2019-2020 following bans on the related compound ephylone. It is not a natural, but a synthetic cathinone. In 2021, eutylone was the most common cathinone identified by the Drug Enforcement Administration in the United States.

<span class="mw-page-title-main">3,4-Dimethylmethcathinone</span> Chemical compound

3,4-Dimethylmethcathinone (3,4-DMMC) is a stimulant drug first reported in 2010 as a designer drug analogue of mephedrone, apparently produced in response to the banning of mephedrone, following its widespread abuse in many countries in Europe and around the world. 3,4-DMMC has been seized as a designer drug in Australia. In vitro, 3,4-DMMC was shown to be a monoamine transporter substrate that potently inhibits norepinephrine and serotonin reuptake, and to a lesser extent dopamine reuptake.

<span class="mw-page-title-main">Pentedrone</span> Pair of enantiomers

Pentedrone is a stimulant of the cathinone class that has been sold as a designer drug and has been found since 2010 as an ingredient in a number of "bath salt" mixes sold as legal highs.

Bath salts are a group of recreational designer drugs. The name derives from instances in which the drugs were disguised as bath salts. The white powder, granules, or crystals often resemble Epsom salts, but differ chemically. The drugs' packaging often states "not for human consumption" in an attempt to circumvent drug prohibition laws. Additionally, they may be mislabeled as plant food, powdered cleaner, and other such products.

<i>N</i>-Ethylbuphedrone Chemical compound

N-Ethylbuphedrone is a stimulant of the cathinone class that has been sold as a designer drug. It is the β-ketone analogue of N,alpha-diethylphenylethylamine.

<span class="mw-page-title-main">3-Methylmethcathinone</span> Substituted cathinone designer drug

3-Methylmethcathinone, also known as 3-MMC and metaphedrone, is a designer drug from the substituted cathinone family. 3-MMC is closely related in structure to the more commonly known illicit drug mephedrone (4-MMC), and is also illegal in most countries that have banned mephedrone due to 3-MMC being a structural isomer of 4-MMC. However, 3-MMC has still appeared on the recreational drug market as an alternative to mephedrone, and was first identified being sold in Sweden in 2012. Unlike some synthetic cathinones, 3-MMC has been evaluated in a least one in large mammal study. 3-MMC is a monoamine transporter substrate that potently inhibits norepinephrine uptake and displays more pronounced dopaminergic vs. serotonergic activity.

<i>alpha</i>-Pyrrolidinohexiophenone Chemical compound

α-Pyrrolidinohexiophenone is a synthetic stimulant drug of the cathinone class developed in the 1960s which has been reported as a novel designer drug.

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

4-Methylbuphedrone, is a stimulant drug of the cathinone class that has been sold online as a designer drug.

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

2-Fluorodeschloroketamine is a dissociative anesthetic related to ketamine. Its sale and use as a designer drug has been reported in various countries. It is an analogue of ketamine where the chlorine group has been replaced by fluorine. Due to its recent emergence, the pharmacological specifics of the compound are mostly unclear, but effects are reported to be similar to its parent compound, ketamine.

<i>N</i>-Ethylhexedrone Chemical compound

N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.

<span class="mw-page-title-main">Bromazolam</span> Triazolobenzodiazepine

Bromazolam (XLI-268) is a triazolobenzodiazepine (TBZD) which was first synthesised in 1976, but was never marketed. It has subsequently been sold as a designer drug, first being definitively identified by the EMCDDA in Sweden in 2016. It is the bromo instead of chloro analogue of alprazolam and has similar sedative and anxiolytic effects to it and other benzodiazepines. Bromazolam is a non subtype selective agonist at the benzodiazepine site of GABAA receptors, with a binding affinity of 2.81nM at the α1 subtype, 0.69nM at α2 and 0.62nM at α5.

<span class="mw-page-title-main">4-EA-NBOMe</span> Chemical compound

4-EA-NBOMe is a substituted amphetamine and 25-NB derivative which has been sold as a designer drug. It was first identified by a forensic laboratory in Germany in 2014, but while its analytical properties and metabolism have been studied, its pharmacology remains unknown.

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

TH-PVP is a substituted cathinone derivative which has been sold as a designer drug. It was first identified by a forensic laboratory in Hungary in 2015, but has subsequently been found in numerous other countries around the world including Spain, Belgium, Poland, Turkey and Brazil. Pharmacological studies in vitro showed it to inhibit reuptake and promote the release of monoamine neurotransmitters with some selectivity for serotonin, but it failed to produce stimulant effects in animals, and has a pharmacological profile more comparable to that of sedating empathogens such as MDAI and 5-Methyl-MDA.

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

2-Methylmethcathinone (2-MMC), also known as ortomephedrone is a recreational designer drug with stimulant effects. It is a substituted cathinone derivative, closely related to better known drugs such as 3-methylmethcathinone and 4-methylmethcathinone (mephedrone). It was first identified in Sweden in 2014, and has subsequently been reported in other European countries such as Poland and Spain.

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

N,N-Dimethylpentylone is a substituted cathinone derivative with stimulant effects, which has been sold as a designer drug, first detected in Sweden in 2014.

References

  1. "EMCDDA–Europol 2010 Annual Report" (PDF). European Monitoring Centre on Drugs and Drug Addiction (EMCDDA). Archived from the original (PDF) on 2012-03-14. Retrieved 2011-10-10.
  2. Andy. "Research on Head Shop drugs in Dublin: Part 2". Drugs.ie. Dublin.
  3. Kelleher C, Christie R, Lalor K, Fox J, Bowden M, O'Donnel C. "An overview of new psychoactive substances and the outlets supplying them" (PDF). Centre for Social and Educational Research, Dublin Institute of Technology. Dublin: National Advisory Committee on Drugs (NACD). Archived from the original (PDF) on 2011-11-25.
  4. Niebel A, Westendorf L, Krumbiegel F, Hartwig S, Parr MK, Tsokos M (August 2021). "Prevalence and concentrations of new designer stimulants, synthetic opioids, benzodiazepines, and hallucinogens in postmortem hair samples: A 13-year retrospective study". Drug Testing and Analysis. 14 (1): 110–121. doi: 10.1002/dta.3150 . PMID   34435749.
  5. Niebel A, Pragst F, Krumbiegel F, Hartwig S (December 2021). "Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs". Forensic Science International. 331: 111148. doi:10.1016/j.forsciint.2021.111148. PMID   34923263. S2CID   245098357.