Pentylone

Last updated
Pentylone
Pentylone.svg
Clinical data
Other namesβ-Keto-Methylbenzodioxolylpentanamine, βk-Methyl-K, βk-MBDP, methylenedioxypentedrone, 1‐(3,4‐methylenedioxyphenyl)‐2‐(methylamino)pentan‐1‐one [1]
ATC code
  • none
Legal status
Legal status
Identifiers
  • (±)-1-(1,3-benzodioxol-5-yl)-2-(methylamino)pentan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H17NO3
Molar mass 235.283 g·mol−1
3D model (JSmol)
  • c2cc1OCOc1cc2C(=O)C(NC)CCC
  • InChI=1S/C13H17NO3/c1-3-4-10(14-2)13(15)9-5-6-11-12(7-9)17-8-16-11/h5-7,10,14H,3-4,8H2,1-2H3 X mark.svgN
  • Key:DFMLULIEUUXXSA-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Pentylone is a stimulant developed in the 1960s. [3] It is a substituted cathinone that has been identified in some samples of powders sold as "NRG-1", along with varying blends of other cathinone derivatives including flephedrone, MDPBP, MDPV, and 4-MePPP. It was also found in combination with 4-MePPP being sold as "NRG-3". [1] Reports indicate side effects include paranoia, agitation, and insomnia, with effects lasting for several days at high doses. [4]

Contents

Pharmacology

Pentylone acts as a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI) and a serotonin releasing agent. [5]

Legality

Pentylone is banned in Canada, Germany, Sweden, the United States, and the United Kingdom. [6] [7]

See also

Related Research Articles

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<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">Methylenedioxypyrovalerone</span> Chemical compound

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α-Pyrrolidinopropiophenone Chemical compound

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<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">3',4'-Methylenedioxy-α-pyrrolidinobutiophenone</span> Stimulant drug

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α-Pyrrolidinopentiophenone Chemical compound

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<span class="mw-page-title-main">Naphyrone</span> Substituted cathinone stimulant drug

Naphyrone, also known as O-2482 and naphthylpyrovalerone, is a substituted cathinone drug derived from pyrovalerone that acts as a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI), 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, or simply 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.

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Eutylone is a stimulant and empathogenic drug of the phenethylamine, amphetamine, phenylisobutylamine, and cathinone families which was 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 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">4-Methylethcathinone</span> Stimulant designer drug

4-Methylethcathinone or 4-MEC is a chemical that bears a chemical resemblance to mephedrone. Due to its similarity to mephedrone, it is thought to be a stimulant and entactogen drug of the phenethylamine, amphetamine, and cathinone chemical classes. It has been marketed alone or in mixtures with other substituted cathinones under the name "NRG-2", although other blends such as "NRG-1" may have been more ambiguous with their ingredients.

<span class="mw-page-title-main">Pentedrone</span> Stimulant designer drug of the cathinone class

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.

α-Pyrrolidinohexiophenone Stimulant drug

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-Chloromethcathinone</span> Simulant drug of the cathinone class

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

<i>N</i>-Ethylhexedrone Stimulant of the cathinone class

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.

<i>N</i>-Ethylpentylone Substituted cathinone stimulant drug

N-Ethylpentylone is a substituted cathinone and stimulant drug which was developed in the 1960s.

<i>N</i>-Ethylpentedrone Designer drug of the substituted cathinone class

N-Ethylpentedrone is a chemical compound of the substituted cathinone class. Since the mid-2010s, NEP has been sold online as a designer drug. It is the N-ethyl analog of pentedrone.

<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">Dipentylone</span> Substituted cathinone stimulant drug

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. 1 2 Brandt SD, Freeman S, Sumnall HR, Measham F, Cole J (September 2011). "Analysis of NRG 'legal highs' in the UK: identification and formation of novel cathinones". Drug Testing and Analysis. 3 (9): 569–575. doi:10.1002/dta.204. PMID   21960541.
  2. Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. GB 1085135,"Substituted phenyl-α-amino ketones.",issued 1969
  4. Bish J (4 August 2017). "Watch Out for Pentylone, the Horrible New MDMA Additive". Vice.
  5. Simmler LD, Rickli A, Hoener MC, Liechti ME (April 2014). "Monoamine transporter and receptor interaction profiles of a new series of designer cathinones". Neuropharmacology. 79: 152–160. doi:10.1016/j.neuropharm.2013.11.008. PMID   24275046. S2CID   25259854.
  6. "Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids are proposed to be classified as a health hazard]. Folkhalsomyndigheten[Public Health Agency of Sweden] (in Swedish). Archived from the original on 25 March 2015. Retrieved 29 June 2015.
  7. "Schedules of Controlled Substances: Temporary Placement of 10 Synthetic Cathinones Into Schedule I". Drug Enforcement Administration. U.S. Federal Register. 7 March 2014.