Naphyrone

Clinical data
Other names	O-2482; Naphthylpyrovalerone
ATC code	none
Legal status
Legal status	DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I[1] Poland: I-P[2]
Identifiers
IUPAC name (RS)-1-naphthalen-2-yl-2-pyrrolidin-1-ylpentan-1-one
CAS Number	850352-53-3 850352-11-3 (hydrochloride)
PubChemCID	11243002
ChemSpider	9418039
UNII	96ON64182B
CompTox Dashboard(EPA)	DTXSID301014192
Chemical and physical data
Formula	C19H23NO
Molar mass	281.399 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCC(C(C1=CC2=C(C=C1)C=CC=C2)=O)N3CCCC3

Naphyrone, also known asO-2482 andnaphthylpyrovalerone,^[3] is astimulantdrug of thecathinone andnaphthylaminopropane families. It was derived frompyrovalerone and acts as aserotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).^[4] Naphyrone has been reported as a noveldesigner drug.^[5] No safety or toxicity data is available on the drug.^[6]

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,^[7][8][9] 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.^[10][11]

Naphyrone emerged as a new legal high in the United Kingdom only months after the ban of similar drugmephedrone (which was also acathinone derivative). Until July 2010 the substance was not controlled by theMisuse 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.^{[citation needed]}

A 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 includedMDPV,flephedrone,mephedrone,butylone andcaffeine, one product tested wasinorganic in composition.^[7] In the case of an individual possessing a product labelled NRG-1 that contains MDPV or other illegal substances, they are in possession of a controlled substance.

On 12 July 2010, theHome Office announced that naphyrone had been banned and made aClass B drug,^[12] following a report from theAdvisory Council on the Misuse of Drugs.^[13][14][15]

As a triple reuptake inhibitor, naphyrone has been shownin vitro to affect thereuptake of theneurotransmittersserotonin,dopamine andnorepinephrine by interacting with theserotonin transporter (SERT),dopamine transporter (DAT), andnorepinephrine transporter (NET).

One study found that thedissociation constant of naphyrone interacting with SERT is 33.1 nM ± 1.1, with DAT is 20.1 nM ± 7.1 and with NET is 136 nM ± 27. Theconcentration of naphyrone required to inhibit the transporters by 50% is 46.0 nM ± 5.5 for SERT, 40.0 nM ± 13 for DAT and 11.7 nM ± 0.9 for NET. Of a number ofpyrovalerone analogues tested, naphyrone was found to be the onlyserotonin–norepinephrine–dopamine reuptake inhibitor found to be active atnM concentrations.^[4]

Some samples of β-naphyrone sold have also been found to contain the alternativeisomer α-naphyrone,^[16] presumably produced accidentally as an impurity in synthesis.^{[17][failed verification]} Thein 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.

Naphyrone is scheduled in the "government decree on psychoactive substances banned from the consumer market".^[18]

• α-PVP
• α-Pyrrolidinopentiothiophenone (α-PVT)
• BMAPN
• HDEP-28
• HDMP-28 (methylnaphthidate)
• MDPV
• Naphthylisopropylamine
• Naphthylpropylaminopentane
• N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
• 2β-Propanoyl-3β-(2-naphthyl)-tropane (WF-23)
• O-2390
• Pronethalol
• Pyrovalerone
• TH-PVP

• Drugs not assigned an ATC code
• Alpha-Propylphenethylamines
• Cathinones
• Designer drugs
• 2-Naphthyl compounds
• Naphthylethylamines
• Propyl compounds
• Pyrrolidinophenones
• Serotonin–norepinephrine–dopamine reuptake inhibitors
• Stimulants

• Articles with short description
• Short description is different from Wikidata
• Drugs with non-standard legal status
• Articles without EBI source
• Chemical pages without DrugBank identifier
• Articles without KEGG source
• Articles without InChI source
• Articles containing unverified chemical infoboxes
• All articles with unsourced statements
• Articles with unsourced statements from December 2019
• All articles with failed verification
• Articles with failed verification from August 2014