Benzylone

Last updated
Benzylone
BMDP structure.png
Identifiers
  • 1-(1,3-benzodioxol-5-yl)-2-(benzylamino)propan-1-one
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H17NO3
Molar mass 283.327 g·mol−1
3D model (JSmol)
  • CC(C(=O)C1=CC2=C(C=C1)OCO2)NCC3=CC=CC=C3
  • InChI=1S/C17H17NO3/c1-12(18-10-13-5-3-2-4-6-13)17(19)14-7-8-15-16(9-14)21-11-20-15/h2-9,12,18H,10-11H2,1H3
  • Key:KRNIYOJEASBDDP-UHFFFAOYSA-N

Benzylone (also known as 3,4-Methylenedioxy-N-benzylcathinone or BMDP), is a recreational designer drug from the substituted cathinone family, with stimulant effects. It has been commonly encountered in seizures of street drug samples but appears to have relatively low potency on its own, being mainly found as a component of mixtures with other related drugs. [1] [2] [3]

See also

Related Research Articles

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine (MDA), sometimes referred to as sass, is an empathogen-entactogen, stimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

<span class="mw-page-title-main">Butylone</span> Entactogen, psychedelic, and stimulant drug of the phenethylamine class

Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine, amphetamine, phenylisobutylamine, and cathinone families. It is the β-keto analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.

<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

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

Ethylone, also known as 3,4-methylenedioxy-N-ethylcathinone, is a recreational designer drug classified as an entactogen, stimulant, and psychedelic of the phenethylamine, amphetamine, and cathinone chemical classes. It is the β-keto analogue of MDEA ("Eve"). Ethylone has only a short history of human use and is reported to be less potent than its relative methylone. In the United States, it began to be found in cathinone products in late 2011.

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

Methylenedioxypyrovalerone 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 US, 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.

α-Pyrrolidinopropiophenone Chemical compound

α-Pyrrolidinopropiophenone (α-PPP), is a stimulant drug. It is similar in structure to the appetite suppressant diethylpropion and has analogous effects in animals. Little is known about this compound, but it has been detected by laboratories in Germany as an ingredient in "ecstasy" tablets seized by law enforcement authorities. This drug has been found to produce stimulant effects in animals and produces highly stimulating effects in humans, based on the experiences of the individuals who have tried it. Most of the individuals who have tried it prefer α-PVP to it, but prefer this drug over α-PVT. It is said to lack euphoria compared to α-PVP.

<span class="mw-page-title-main">Substituted methylenedioxyphenethylamine</span> Class of psychoactive drugs

The substituted methylenedioxyphenethylamines represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational substances.

<span class="mw-page-title-main">1,3-Benzodioxolylbutanamine</span> Enactogenic drug of the phenethylamine class

1,3-Benzodioxolylbutanamine is an entactogenic drug of the phenethylamine, amphetamine, and phenylisobutylamine families. It is the α-ethyl analog of MDPEA and MDA and the methylenedioxy analogue of α-ethylphenethylamine.

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

1-(3,4-Methylenedioxybenzyl)piperazine is a chemical compound of the piperazine chemical class related to benzylpiperazine (BZP). MDBZP has been sold as a designer drug and has even been found as an ingredient in street Ecstasy pills.

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

Methylenedioxybenzylamphetamine, abbreviated MDBZ, and systematically named 3,4-methylenedioxy-N-benzylamphetamine, is a psychedelic drug. It is the N-benzyl derivative of 3,4-methylenedioxyamphetamine (MDA). MDBZ was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 150 mg, and the duration unknown. Very few data exist about the pharmacological properties, metabolism, and toxicity of MDBZ.

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

3,4-Methylenedioxy-N,N-dimethylamphetamine is a lesser-known research chemical. It is also the N,N-dimethyl analog of 3,4-methylenedioxyamphetamine (MDA). MDDM was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage is unspecified and the duration unknown. MDDM produces only mild effects that are not well characterized in PiHKAL. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDDM. This compound is however occasionally encountered as an impurity in 3,4-methylenedioxy-N-methylamphetamine (MDMA) which has been synthesized by methylation of MDA using methylating reagents such as methyl iodide. An excess of reagent or a reaction temperature that is too high results in some double methylation of the amine nitrogen, yielding MDDM as well as MDMA. The presence of MDDM as an impurity can thus reveal which synthetic route was used to manufacture seized samples of MDMA.

<span class="mw-page-title-main">3',4'-Methylenedioxy-α-pyrrolidinopropiophenone</span> Stimulant drug

3',4'-Methylenedioxy-α-pyrrolidinopropiophenone (MDPPP) is a stimulant designer drug. It was sold in Germany in the late 1990s and early 2000s as an ingredient in imitation ecstasy (MDMA) pills. It shares a similar chemical structure with α-PPP and MDPV, and has been shown to have reinforcing effects in rats.

<span class="mw-page-title-main">4'-Methyl-α-pyrrolidinopropiophenone</span> Chemical compound

4'-Methyl-α-pyrrolidinopropiophenone is a stimulant drug and substituted cathinone. It is structurally very similar to α-PPP, with only one added methyl group in the para position on the phenyl ring. 4-MePPP was sold in Germany as a designer drug in the late 1990s and early 2000s, along with a number of other pyrrolidinophenone derivatives. Although it has never achieved the same international popularity as its better-known relations α-PPP and MDPV, 4-MePPP is still sometimes found as an ingredient of grey-market "bath salt" blends such as "NRG-3".

<span class="mw-page-title-main">4'-Methoxy-α-pyrrolidinopropiophenone</span> Stimulant recreational drug

4'-Methoxy-α-pyrrolidinopropiophenone (MOPPP) is a stimulant designer drug of the pyrrolidinophenone class. It has the potential to produce euphoria, an effect shared with other classical stimulants.

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

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects.

<span class="mw-page-title-main">3',4'-Methylenedioxy-α-pyrrolidinobutiophenone</span> Stimulant drug

3',4'-Methylenedioxy-α-pyrrolidinobutyrophenone (MDPBP) is a stimulant of the cathinone class developed in the 1960s, which has been reported as a novel designer drug. MDPBP is sometimes sold under the name "NRG-1" as a mixture with other cathinone derivatives, including flephedrone, pentylone, MαPPP and its higher homologue MDPV. As with other cathinones, MDPBP has been shown to have reinforcing effects in rats.

α-Pyrrolidinopentiophenone Chemical compound

α-Pyrrolidinopentiophenone (α-PVP), also known as α-pyrrolidinovalerophenone, O-2387, β-keto-prolintane, prolintanone, or desmethylpyrovalerone, is a synthetic stimulant of the cathinone class developed in the 1960s that has been sold as a designer drug and often consumed for recreational reasons. α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.

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

3,4-Methylenedioxycathinone is an empathogen and stimulant of the phenethylamine, amphetamine, and cathinone classes and the β-keto analogue of MDA.

<span class="mw-page-title-main">5-Methylethylone</span> Chemical compound

5-Methylethylone is an empathogen, stimulant and psychedelic drug of the amphetamine, phenethylamine, and cathinone chemical classes. It is structurally related to ethylone, a novel designer drug. Relatively little data exists about the pharmacological properties, metabolism, and toxicity of 5-methylethylone, though it has been sold as a designer drug.

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

MDPHP (3',4'-Methylenedioxy-α-pyrrolidinohexiophenone) is a stimulant of the cathinone class originally developed in the 1960s, which has been reported as a novel designer drug. In the UK its slang name is monkey dust. It is closely related to the potent stimulant MDPV though with slightly milder effects, and has been used as an alternative in some countries following the banning of MDPV.

References

  1. Mueller DM, Rentsch KM (February 2012). "Generation of metabolites by an automated online metabolism method using human liver microsomes with subsequent identification by LC-MS(n), and metabolism of 11 cathinones" (PDF). Analytical and Bioanalytical Chemistry. 402 (6): 2141–2151. doi:10.1007/s00216-011-5678-8. PMID   22231510. S2CID   27846319.
  2. Fornal E, Stachniuk A, Wojtyla A (January 2013). "LC-Q/TOF mass spectrometry data driven identification and spectroscopic characterisation of a new 3,4-methylenedioxy-N-benzyl cathinone (BMDP)". Journal of Pharmaceutical and Biomedical Analysis. 72: 139–144. doi:10.1016/j.jpba.2012.09.019. PMID   23146238.
  3. Critical Review Report: 3,4-Methylenedioxy-N-benzylcathinone (Benzylone, BMDP). World Health Organization. Expert Committee on Drug Dependence Forty-fourth Meeting, Geneva, 11-15 October 2021