Pentedrone

Pentedrone (also known as α-methylaminovalerophenone) 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.[1][2][3][4][5][6][7]

Pentedrone
Clinical data
ATC code
  • none
Legal status
Legal status
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
Identifiers
IUPAC name
  • (±)-1-phenyl-2-(methylamino)pentan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.231.338
Chemical and physical data
FormulaC12H17NO
Molar mass191.274 g·mol−1
3D model (JSmol)
SMILES
  • O=C(C(CCC)NC)C1=CC=CC=C1
InChI
  • InChI=1S/C12H17NO/c1-3-7-11(13-2)12(14)10-8-5-4-6-9-10/h4-6,8-9,11,13H,3,7H2,1-2H3 Y
  • Key:WLIWIUNEJRETFX-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Pharmacology

Pentedrone acts as a norepinephrine-dopamine reuptake inhibitor without causing their release, the same mechanism of action as methylphenidate.[8][9]

Side effects

Pentedrone has been linked to at least one death where it was combined with α-PVP and caused heart failure.[10]

Detection

A forensic standard of Pentedrone is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[11]

On January 28, 2014, the DEA listed it, along with nine other synthetic cathinones, on the Schedule 1 with a temporary ban, effective February 27, 2014.[12]

Pentedrone is an Anlage II controlled drug in Germany.

As of October 2015 Pentedrone is a controlled substance in China.[13]

Pentedrone is banned in the Czech Republic.[14]

See also

References
  1. EMCDDA Annual Report 2010
  2. Research on Head Shop drugs in Dublin: Part 2
  3. An overview of new psychoactive substances and the outlets supplying them
  4. Westphal F, Junge T, Girreser U, Greibl W, Doering C (April 2012). "Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products". Forensic Science International. 217 (1–3): 157–67. doi:10.1016/j.forsciint.2011.10.045. PMID 22115724.
  5. Maheux CR, Copeland CR (January 2012). "Chemical analysis of two new designer drugs: buphedrone and pentedrone". Drug Testing and Analysis. 4 (1): 17–23. doi:10.1002/dta.385. PMID 22113925. S2CID 3250022.
  6. Poklis JL, Wolf CE, ElJordi OI, Liu K, Zhang S, Poklis A (January 2015). "Analysis of the first- and second-generation Raving Dragon Novelty Bath Salts containing methylone and pentedrone". Journal of Forensic Sciences. 60 Suppl 1 (11): S234–40. doi:10.1111/1556-4029.12629. PMID 25470207. S2CID 38295463.
  7. Zancajo VM, Brito J, Carrasco MP, Bronze MR, Moreira R, Lopes A (November 2014). "Analytical profiles of "legal highs" containing cathinones available in the area of Lisbon, Portugal". Forensic Science International. 244: 102–10. doi:10.1016/j.forsciint.2014.08.010. hdl:10400.26/7695. PMID 25240621.
  8. 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: 152–60. doi:10.1016/j.neuropharm.2013.11.008. PMID 24275046. S2CID 25259854.
  9. Hwang JY, Kim JS, Oh JH, Hong SI, Ma SX, Jung YH, Ko YH, Lee SY, Kim HC, Jang CG (January 2017). "The new stimulant designer compound pentedrone exhibits rewarding properties and affects dopaminergic activity". Addiction Biology. 22 (1): 117–128. doi:10.1111/adb.12299. PMID 26290055. S2CID 23807079.
  10. Sykutera M, Cychowska M, Bloch-Boguslawska E (May 2015). "A Fatal Case of Pentedrone and α-Pyrrolidinovalerophenone Poisoning". Journal of Analytical Toxicology. 39 (4): 324–9. doi:10.1093/jat/bkv011. PMID 25737339.
  11. "Pentedrone". Southern Association of Forensic Scientists. Retrieved 8 September 2015.
  12. "Temporary Placement of 10 Synthetic Cathinones into Schedule I". 28 January 2014.
  13. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  14. "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví.


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