Pentedrone
{{Short description|Stimulant designer drug of the cathinone class}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 457956777
| IUPAC_name = (±)-1-phenyl-2-(methylamino)pentan-1-one
| image = Pentedrone.svg
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| tradename =
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| legal_status =
| legal_AU =
| legal_BR = F2
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}
| legal_US = Schedule I
| legal_UK = Class B
| legal_DE = Anlage II
| legal_UN = P II
| legal_UN_comment = {{Cite web |title=Substance Details Pentedrone |url=https://www.unodc.org/LSS/Substance/Details/1e25cb1f-9760-4cd8-9032-fcf11461e4e7 |access-date=2024-01-22}}
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 879722-57-3
| ATC_prefix = none
| ATC_suffix =
| PubChem = 71750191
| KEGG = C22784
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2ELU1B757Q
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 26286729
| synonyms = α-Methylaminovalerophenone; α-Propyl-β-keto-N-methylphenethylamine; α-Desmethyl-α-propyl-N-methylcathinone; α-Desmethyl-α-propylmethcathinone; α-Desmethyl-α-propyl-β-keto-N-methylamphetamine; α-Desmethyl-α-propyl-β-ketomethamphetamine
| C=12 | H=17 | N=1 | O=1
| SMILES = O=C(C(CCC)NC)C1=CC=CC=C1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WLIWIUNEJRETFX-UHFFFAOYSA-N
}}
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.{{Cite web |url=http://www.emcdda.europa.eu/attachements.cfm/att_132857_EN_EMCDDA-Europol%20Annual%20Report%202010A.pdf |title=EMCDDA Annual Report 2010 |access-date=2011-10-15 |archive-date=2012-03-14 |archive-url=https://web.archive.org/web/20120314043454/http://www.emcdda.europa.eu/attachements.cfm/att_132857_EN_EMCDDA-Europol%20Annual%20Report%202010A.pdf |url-status=dead }}[http://www.drugs.ie/features/feature/research_on_head_shop_drugs_in_dublin_part_2 Research on Head Shop drugs in Dublin: Part 2][http://www.dit.ie/cser/media/ditcser/documents/Head_Report2011_overview.pdf An overview of new psychoactive substances and the outlets supplying them]{{cite journal | vauthors = Westphal F, Junge T, Girreser U, Greibl W, Doering C | title = Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products | journal = Forensic Science International | volume = 217 | issue = 1–3 | pages = 157–67 | date = April 2012 | pmid = 22115724 | doi = 10.1016/j.forsciint.2011.10.045 | url = http://www.fsijournal.org/article/S0379-0738%2811%2900533-0/abstract | url-access = subscription }}{{cite journal | vauthors = Maheux CR, Copeland CR | title = Chemical analysis of two new designer drugs: buphedrone and pentedrone | journal = Drug Testing and Analysis | volume = 4 | issue = 1 | pages = 17–23 | date = January 2012 | pmid = 22113925 | doi = 10.1002/dta.385 | s2cid = 3250022 }}{{cite journal | vauthors = Poklis JL, Wolf CE, ElJordi OI, Liu K, Zhang S, Poklis A | title = Analysis of the first- and second-generation Raving Dragon Novelty Bath Salts containing methylone and pentedrone | journal = Journal of Forensic Sciences | volume = 60 Suppl 1 | issue = 11 | pages = S234–40 | date = January 2015 | pmid = 25470207 | doi = 10.1111/1556-4029.12629 | s2cid = 38295463 }}{{cite journal | vauthors = Zancajo VM, Brito J, Carrasco MP, Bronze MR, Moreira R, Lopes A | title = Analytical profiles of "legal highs" containing cathinones available in the area of Lisbon, Portugal | journal = Forensic Science International | volume = 244 | pages = 102–10 | date = November 2014 | pmid = 25240621 | doi = 10.1016/j.forsciint.2014.08.010 | url = http://www.fsijournal.org/article/S0379-0738%2814%2900324-7/abstract | hdl = 10400.26/7695 | hdl-access = free }}
Pharmacology
Pentedrone acts as a norepinephrine-dopamine reuptake inhibitor (NDRI) without inducing monoamine release, a similar mechanism of action to methylphenidate.{{cite journal | vauthors = Simmler LD, Rickli A, Hoener MC, Liechti ME | title = Monoamine transporter and receptor interaction profiles of a new series of designer cathinones | journal = Neuropharmacology | volume = 79 | pages = 152–160 | date = April 2014 | pmid = 24275046 | doi = 10.1016/j.neuropharm.2013.11.008 | s2cid = 25259854 | url = http://onlinelibrary.wiley.com/doi/10.1002/dta.385/abstract | url-access = subscription }}{{cite journal | vauthors = Hwang JY, Kim JS, Oh JH, Hong SI, Ma SX, Jung YH, Ko YH, Lee SY, Kim HC, Jang CG | title = The new stimulant designer compound pentedrone exhibits rewarding properties and affects dopaminergic activity | journal = Addiction Biology | volume = 22 | issue = 1 | pages = 117–128 | date = January 2017 | pmid = 26290055 | doi = 10.1111/adb.12299 | s2cid = 23807079 }} Its {{Abbrlink|IC50|half-maximal inhibitory concentration}} values for inhibition of monoamine reuptake have been reported to be 610{{nbsp}}nM for norepinephrine, 2,500{{nbsp}}μM for dopamine, and 135,000{{nbsp}}μM for serotonin. In rodents, pentedrone has been found to produce conditioned place preference (CPP), to be self-administered, and to dose-dependently stimulate locomotor activity. Hence, pentedrone shows psychostimulant-like and reinforcing effects in animals.
Side effects
Pentedrone has been linked to at least one death where it was combined with α-PVP and caused heart failure.{{cite journal | vauthors = Sykutera M, Cychowska M, Bloch-Boguslawska E | title = A Fatal Case of Pentedrone and α-Pyrrolidinovalerophenone Poisoning | journal = Journal of Analytical Toxicology | volume = 39 | issue = 4 | pages = 324–9 | date = May 2015 | pmid = 25737339 | doi = 10.1093/jat/bkv011 | doi-access = }}
Detection
A forensic standard of pentedrone is available, and the compound has been posted on the Forendex website of potential drugs of abuse.{{cite web | url=http://forendex.southernforensic.org/index.php/detail/index/1164 | title=Pentedrone | publisher=Southern Association of Forensic Scientists | access-date=8 September 2015}}
Legal status
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.{{cite web |url=http://www.deadiversion.usdoj.gov/fed_regs/rules/2014/fr0128.htm |date=28 January 2014 |title=Temporary Placement of 10 Synthetic Cathinones into Schedule I |access-date=16 February 2014 |archive-date=17 October 2016 |archive-url=https://web.archive.org/web/20161017130614/https://www.deadiversion.usdoj.gov/fed_regs/rules/2014/fr0128.htm |url-status=dead }}
Pentedrone is an Anlage II controlled drug in Germany.
As of October 2015 Pentedrone is a controlled substance in China.{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}
Pentedrone is banned in the Slovak Republic.{{Cite web |title=Zoznam omamných látok a psychotropných látok zaradených do I., II. A III. skupiny (ochrana pred omamnými látkami) {{!}} Lewik |url=https://www.lewik.org/term/2965/zoznam-omamnych-latok-a-psychotropnych-latok-zaradenych-do-i-ii-a-iii-skupiny-ochrana-pred-omamnymi-latkami/ |access-date=2024-06-19 |website=www.lewik.org}}
See also
References
{{Reflist}}
{{Stimulants}}
{{Monoamine reuptake inhibitors}}
{{Phenethylamines}}
Category:Alpha-Propylphenethylamines