Naphyrone

Naphyrone
Systematic (IUPAC) name
1-naphthalen-2-yl-2-pyrrolidin-1-ylpentan-1-one
Clinical data
Pregnancy cat.  ?
Legal status Class B (UK), I-P(Poland)[1]
Identifiers
CAS number 850352-53-3
850352-11-3 (hydrochloride)
ATC code None
PubChem CID 11243002
ChemSpider 9418039
Chemical data
Formula C19H23NO 
Mol. mass 281.391 g/mol
SMILES eMolecules & PubChem

Naphyrone also known as O-2482 and naphthylpyrovalerone,[2] is a drug derived from pyrovalerone that acts as a triple reuptake inhibitor,[3] producing stimulant effects and has been reported as a novel designer drug.[4] No safety or toxicity data is available on the drug.[5]

The drug has been marketed under the name NRG-1, although only a minority of samples of substances sold under this name have been found to actually contain naphyrone,[6][7] and even samples that proved to contain genuine β-naphyrone were in some cases also found to contain the 1-naphthyl isomer α-naphyrone in varying proportions, further confusing the reported effects profile.[8][9]

Contents

Use in the United Kingdom

Naphyrone emerged as a new legal high in the United Kingdom only months after the ban of similar drug mephedrone (which was also a cathinone derivative). Until July 2010 the substance was not controlled by the Misuse of Drugs Act 1971 and was therefore not illegal for someone to possess. The Medicines Act prevented naphyrone from being sold for human consumption, and therefore it was sometimes sold as 'pond cleaner' or as another substance not normally consumed by humans. In response to this emerging trend of new legal highs, Home Office Minister James Brokenshire said "Action to address the issue of emerging legal highs coming on to the market is a priority for the Government."[10][unreliable source?]

A batch analysis report from the drugs information site Drugs-Forum.com dated 12 June 2010 found that some products labelled as NRG-1 contain the Class B substances MDPV and flephedrone.[11] In the case of an individual possessing a product labelled NRG-1 that contains MDPV, they are in possession of a controlled substance. A subsequent study by researchers at Liverpool John Moores University found that only one out of ten products labelled as "NRG-1" actually contained naphyrone when they were subjected to laboratory analysis. Compounds found in products labelled NRG-1 included MDPV, flephedrone, mephedrone, butylone and caffeine, one product tested was inorganic in composition.[6]

On 12 July 2010 the Home Office announced that naphyrone has been banned and made a Class B drug,[12] following a report from the Advisory Council on the Misuse of Drugs.[13][14][15]

Pharmacology

As a triple reuptake inhibitor, naphyrone has been shown in vitro to affect the reuptake of the neurotransmitters serotonin, dopamine and norepinephrine by interacting with the serotonin transporter (SERT), dopamine transporter (DAT), and norepinephrine transporter (NET).

One study found that the dissociation constant of naphyrone interacting with SERT is 33.1nM ± 1.1, with DAT is 20.1nM ± 7.1 and with NET is 136nM ± 27. The concentration of naphyrone required to inhibit the transporters by 50% is 46.0nM ± 5.5 for SERT, 40.0nM ± 13 for DAT and 11.7nM ± 0.9 for NET. Of a number of pyrovalerone analogues tested, naphyrone was found to be the only triple reuptake inhibitor found to be active at nM concentrations.[3]

Some samples of genuine β-naphyrone sold as "legal highs" have also been found to contain the alternative isomer α-naphyrone, presumably produced accidentally as an impurity in synthesis.[16] The in vitro data available in the scientific literature was all obtained using pure β-naphyrone, and the pharmacological properties of α-naphyrone are unknown, further complicating the pharmacological profile of this little studied designer drug.

α-naphyrone

See also

References

  1. ^ = WDU20111050614 "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. http://isap.sejm.gov.pl/DetailsServlet?id = WDU20111050614. Retrieved 17 June 2011. 
  2. ^ "Deadly New 'Legal' Drug Bound For Britain - Yahoo! News UK". Uk.news.yahoo.com. 2010-03-31. http://uk.news.yahoo.com/5/20100331/twl-deadly-new-legal-drug-bound-for-brit-3fd0ae9.html. Retrieved 2010-04-03. [dead link]
  3. ^ a b Meltzer PC, Butler D, Deschamps JR, Madras BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors. Journal of Medicinal Chemistry. 2006 Feb 23;49(4):1420-32. doi:10.1021/jm050797a PMID 16480278
  4. ^ Alan Travis, home affairs editor (2010-04-01). "NRG-1 may be next legal high to face ban by ministers | Politics". The Guardian. http://www.guardian.co.uk/politics/2010/apr/01/nrg1-legal-high-ban-considered. Retrieved 2010-04-03. 
  5. ^ Lavery, Michael (2 April 2010). "New 50c legal drug 'is more evil' than any head shop high". The Herald. http://www.herald.ie/national-news/new-50c-legal-drug-is-more-evil-than-any-head-shop-high-2122823.html. Retrieved 2 April 2010. 
  6. ^ a b Brandt, S. D.; Sumnall, H. R.; Measham, F.; Cole, J. (2010). "4-fmc infomail: rc_hu@yahoo.com". BMJ 341: c3564. doi:10.1136/bmj.c3564. PMID 20605894.  edit
  7. ^ Brandt SD, Sumnall HR, Measham F, Cole J (August 2010). "Analyses of second-generation 'legal highs' in the UK: initial findings". Drug Testing and Analysis 2 (8): 377–82. doi:10.1002/dta.155. PMID 20687197. 
  8. ^ Brandt SD, Wootton RC, De Paoli G, Freeman S (October 2010). "The naphyrone story: The alpha or beta-naphthyl isomer?". Drug Testing and Analysis 2 (10): 496–502. doi:10.1002/dta.185. PMID 20886463. 
  9. ^ De Paoli G, Maskell PD, Pounder DJ (February 2011). "Naphyrone: analytical profile of the new "legal high" substitute for mephedrone". Journal of Forensic and Legal Medicine 18 (2): 93. doi:10.1016/j.jflm.2010.12.001. PMID 21315306. 
  10. ^ Francis, Nick (2010-05-24). "Next meow meow to hit clubs and festivals | The Sun |Features". The Sun. http://www.thesun.co.uk/sol/homepage/features/2984320/Next-meow-meow-to-hit-clubs-and-festivals.html. Retrieved 2010-07-17. 
  11. ^ 11:47. "File Archive". Drugs Forum. http://www.drugs-forum.com/forum/local_links.php?action=jump&catid=245&id=9184. Retrieved 2010-07-17. 
  12. ^ "NRG-1 'legal high' drug is banned". BBC News. 2010-07-12. http://news.bbc.co.uk/1/hi/uk/10602398.stm. Retrieved 2010-07-17. 
  13. ^ "Advisory Council on the Misuse of Drugs Naphyrone Report (2010)". Home Office. 2010-07-07. http://www.homeoffice.gov.uk/publications/drugs/acmd1/naphyrone-report. Retrieved 2010-07-17. 
  14. ^ "The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799". Opsi.gov.uk. http://www.opsi.gov.uk/si/si2010/pdf/uksi_20101799_en.pdf. Retrieved 2010-07-18. 
  15. ^ "Explanatory Memorandum To The Misuse of Drugs (Amendment No. 2) (England, Wales and Scotland) Regulations 2010 No. 1799". Opsi.gov.uk. http://www.opsi.gov.uk/si/si2010/em/uksiem_20101799_en.pdf. Retrieved 2010-07-18. 
  16. ^ An overview of new psychoactive substances and the outlets supplying them

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