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Revision as of 19:34, 20 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'DrugBank_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Dr← Previous edit Latest revision as of 20:56, 2 December 2024 edit undoWikiCleanerBot (talk | contribs)Bots926,203 editsm v2.05b - Bot T5 CW#16 - Fix errors for CW project (Unicode control characters)Tag: WPCleaner 
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{{Short description|Stimulant drug of the substituted cathinone class}}
{{Redirect|NRG-3|the protein growth factor|Neuregulin 3}}

{{Drugbox {{Drugbox
| Verifiedfields = changed
⚫ | verifiedrevid = 449584422
| Watchedfields = changed
⚫ | verifiedrevid = 451552327
| IUPAC_name = (±)-1-(1,3-benzodioxol-5-yl)-2-(methylamino)pentan-1-one | IUPAC_name = (±)-1-(1,3-benzodioxol-5-yl)-2-(methylamino)pentan-1-one
| image = Pentylone_structure.png | image = Pentylone.svg

<!--Clinical data-->
| tradename =
| pregnancy_category =
| legal_status =
⚫ | routes_of_administration =


<!--Pharmacokinetic data--> <!--Clinical data-->| tradename =
| bioavailability = | pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
⚫ | protein_bound =
| metabolism = | legal_BR = F2
| legal_BR_comment = <ref>{{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=] |language=pt-BR |publication-date=2023-07-25}}</ref>
⚫ | elimination_half-life =
| excretion = | legal_DE = Anlage I
| legal_UK = Class B

| legal_US = Schedule I
⚫ <!--Identifiers-->
| legal_status = Illegal in Sweden and Finland
⚫ | routes_of_administration = <!--Pharmacokinetic data-->
| bioavailability =
⚫ | protein_bound =
| metabolism =
⚫ | elimination_half-life =
⚫ | excretion = <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 698963-77-8 | CAS_number = 698963-77-8
| CAS_supplemental = <BR>17763-01-8 (hydrochloride) | CAS_supplemental = <BR>17763-01-8 (hydrochloride)
| UNII_Ref = {{fdacite|correct|FDA}}
| synonyms = β-Keto-Methylbenzodioxolylpentanamine, βk-Methyl-K, βk-MBDP, methylenedioxypentedrone, 1‐(3,4‐methylenedioxyphenyl)‐2‐(methylamino)pentan‐1‐one<ref name="pmid21960541" />
| UNII = IGN39WGH0Q
| ATC_prefix = none | ATC_prefix = none
| ATC_suffix = | ATC_suffix =
| PubChem = | PubChem = 60208608
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 29786041
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = DFMLULIEUUXXSA-UHFFFAOYSA-N


<!--Chemical data--> <!--Chemical data-->| C = 13
| C=13 | H=17 | N=1 | O=3 | H = 17
| N = 1
| molecular_weight = 235.278 g/mol
| O = 3
| smiles = c2cc1OCOc1cc2C(=O)C(NC)CCC | smiles = c2cc1OCOc1cc2C(=O)C(NC)CCC
}} }}


'''β-Keto-Methylbenzodioxolylpentanamine''' ('''Pentylone''', '''bk-Methyl-K''', '''bk-MBDP''') is a ] compound developed in the 1960s,<ref>Substituted phenyl-α-amino ketones. British Patent GB 1085135 (1969).</ref> which has been reported as a novel ], identified in some samples of powders sold as "NRG-1" and "NRG-3", along with varying blends of other ] derivatives including ], ], ] and ].<ref name="pmid21191917">{{cite journal |author=Brandt SD, Freeman S, Sumnall HR, Measham F, Cole J |title=Analysis of NRG 'legal highs' in the UK: identification and formation of novel cathinones |journal=Drug Testing and Analysis |volume= |issue= |pages= |year=2010 |month=December |pmid=21191917 |doi=10.1002/dta.204 |url=}}</ref> '''Pentylone''' is a ] developed in the 1960s.<ref>{{cite patent | title = Substituted phenyl-α-amino ketones. | country = GB | number = 1085135 | gdate = 1969 }}</ref> It is a ] that has been identified in some samples of powders sold as "NRG-1", along with varying blends of other cathinone derivatives including ], ], ], and ].
It was also found in combination with 4-MePPP being sold as "NRG-3".<ref name="pmid21960541">{{cite journal | vauthors = Brandt SD, Freeman S, Sumnall HR, Measham F, Cole J | title = Analysis of NRG 'legal highs' in the UK: identification and formation of novel cathinones | journal = Drug Testing and Analysis | volume = 3 | issue = 9 | pages = 569–575 | date = September 2011 | pmid = 21960541 | doi = 10.1002/dta.204 }}</ref> Reports indicate side effects include ], ], and ], with effects lasting for several days at high doses.<ref>{{cite journal | vauthors = Bish J |title= Watch Out for Pentylone, the Horrible New MDMA Additive |journal=Vice |date=4 August 2017 |url= https://www.vice.com/en_uk/article/pagjxg/watch-out-for-pentylone-the-horrible-new-mdma-additive}}</ref>

==Pharmacology==

Pentylone acts as a ] (SNDRI) and a ].<ref>{{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 }}</ref>

==Legality==
Pentylone is banned in Canada, Germany, Sweden, the United States, and the United Kingdom.<ref>{{cite web | url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/november/cannabinoider-foreslas-bli-klassade-som-halsofarlig-vara/ | title=Cannabinoider föreslås bli klassade som hälsofarlig vara | trans-title = Cannabinoids are proposed to be classified as a health hazard | archive-url = https://web.archive.org/web/20150325081230/http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/november/cannabinoider-foreslas-bli-klassade-som-halsofarlig-vara/ | archive-date = 25 March 2015 | language=sv | access-date=29 June 2015 | work = Folkhalsomyndigheten | trans-work = Public Health Agency of Sweden }}</ref><ref>{{cite web | url = https://www.federalregister.gov/articles/2014/03/07/2014-04997/schedules-of-controlled-substances-temporary-placement-of-10-synthetic-cathinones-into-schedule-i | title = Schedules of Controlled Substances: Temporary Placement of 10 Synthetic Cathinones Into Schedule I | publisher = U.S. Federal Register | work = Drug Enforcement Administration | date = 7 March 2014 }}</ref>


== See also == == See also ==
* ] * ]
* ] * ]
* ]
* ] (MDPV) * ] (MDPV)
* ] * ]
* ] * ]
* ]


== References == == References ==
{{Reflist}} {{Reflist}}



{{Stimulants}} {{Stimulants}}
{{Adrenergics}}
{{Dopaminergics}}
{{Serotonergics}} {{Serotonergics}}
{{Phenethylamines}} {{Phenethylamines}}
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{{nervous-system-drug-stub}} {{nervous-system-drug-stub}}