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{{Short description|Chemical compound}} |
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{{DISPLAYTITLE:''alpha''-Pyrrolidinopentiophenone}} |
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{{lowercase title}} |
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{{drugbox |
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{{About|the drug substance α-PVP|the pharmaceutical excipient called PVP|polyvinylpyrrolidone}} |
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| verifiedrevid = 413314097 |
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{{Drugbox |
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| drug_name = ''alpha''-Pyrrolidinopentiophenone |
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| Verifiedfields = changed |
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| IUPAC_name = 1-phenyl-2-(1-pyrrolidinyl)-1-pentanone |
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| Watchedfields = changed |
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| image = aPVP_structure.png |
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| class = ]; ] (NDRI) |
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| width = 200px |
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| verifiedrevid = 413315866 |
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| type = |
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| IUPAC_name = (''RS'')-1-Phenyl-2-(pyrrolidin-1-yl)pentan-1-one |
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| image = Alpha-Pyrrolidinopentiophenone.svg |
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| alt = |
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| caption = |
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| image2 = Alpha-PVP molecule ball.png |
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| alt2 = Ball-and-stick model of the alpha-PVP molecule |
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| drug_name = α-Pyrrolidinopentiophenone |
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<!--Clinical data-->| tradename = |
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| MedlinePlus = |
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| licence_EU = |
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| licence_US = |
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| pregnancy_AU = |
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| pregnancy_category = |
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| legal_AU = S8<!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_BR = F2 |
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| 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> |
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| legal_CA = Unscheduled |
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| legal_UK = Class B |
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| legal_US = Schedule I |
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| legal_DE = Anlage II |
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| legal_NZ = Unscheduled |
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| legal_UN = P II |
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| addiction_liability = Very high |
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| routes_of_administration = ], ], ], ], ] |
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<!--Pharmacokinetic data-->| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = 2 hours |
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| duration_of_action = 3–5 hours |
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| excretion = <!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 14530-33-7 |
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| CAS_supplemental = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C22754 |
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| ATC_prefix = None |
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| ATC_suffix = |
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| PubChem = 11148955 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 9324063 |
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| ChemSpiderID = 9324063 |
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| InChI = 1/C15H21NO/c1-2-8-14(16-11-6-7-12-16)15(17)13-9-4-3-5-10-13/h3-5,9-10,14H,2,6-8,11-12H2,1H3 |
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| InChIKey = YDIIDRWHPFMLGR-UHFFFAOYAL |
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| smiles1 = O=C(c1ccccc1)C(N2CCCC2)CCC |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| synonyms = α-pyrrolidinovalerophenone, α-PVP, O-2387, β-keto-prolintane, prolintanone, desmethylpyrovalerone |
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| ChEMBL = 205082 |
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| ChEMBL = 205082 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 767K3AWA4R |
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<!--Chemical data-->| C = 15 |
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| H = 21 |
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| N = 1 |
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| O = 1 |
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| smiles = CCCC(C(C1=CC=CC=C1)=O)N2CCCC2 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C15H21NO/c1-2-8-14(16-11-6-7-12-16)15(17)13-9-4-3-5-10-13/h3-5,9-10,14H,2,6-8,11-12H2,1H3 |
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| StdInChI = 1S/C15H21NO/c1-2-8-14(16-11-6-7-12-16)15(17)13-9-4-3-5-10-13/h3-5,9-10,14H,2,6-8,11-12H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = YDIIDRWHPFMLGR-UHFFFAOYSA-N |
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| StdInChIKey = YDIIDRWHPFMLGR-UHFFFAOYSA-N |
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| CAS_number = 14530-33-7 |
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| CAS_supplemental = <BR>5485-65-4 (]) |
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| ATC_prefix = |
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| ATC_suffix = |
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| PubChem = 11148955 |
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| DrugBank = |
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| C=15|H=21|N=1|O=1 |
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| molecular_weight = 231.333 g/mol |
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| smiles = C1CCCN1C(CCC)C(=O)c2ccccc2 |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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}} |
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}} |
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'''α-Pyrrolidinopentiophenone''' or '''α-PVP''' is a ] compound developed in the 1960s and related to ],<ref>which has been reported as a novel ].<ref>Sauer C, Peters FT, Haas C, Meyer MR, Fritschi G, Maurer HH. New designer drug alpha-pyrrolidinovalerophenone (PVP): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques. ''Journal of Mass Spectrometry''. 2009 Jun;44(6):952-64. PMID: 19241365</ref> |
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'''α-Pyrrolidinopentiophenone''' ('''α-PVP'''), also known as '''α-pyrrolidinovalerophenone''', '''O-2387''', '''β-keto-prolintane''', '''prolintanone''',<ref>{{Cite web |date=May 9, 2023 |title=PubChem Substance Record for SID 481087126, alpha-PVP |url=https://pubchem.ncbi.nlm.nih.gov/substance/481087126 |access-date=May 7, 2024 |publisher=]}}</ref><ref>{{Cite web |date=March 3, 2023 |title=PubChem Substance Record for SID 172113243, alpha-Pyrrolidinovalerophenone |url=https://pubchem.ncbi.nlm.nih.gov/substance/172113243 |access-date=May 7, 2024 |publisher=]}}</ref> or '''desmethylpyrovalerone''', is a synthetic ] of the ] class developed in the 1960s that has been sold as a ] and often consumed for ].<ref>{{cite patent | title = α-Pyrrolidinovalerophenones | pubdate = May 29, 1963 | country = GB | number = 927475}}</ref><ref>{{cite web | vauthors = Logan BK |url=http://www.soft-tox.org/files/Designer_Drugs/Alpha-PVP.pdf |title=SOFT Designer Drug Committee Monographs: Alpha-PVP |date=September 13, 2013 |publisher=Society of Forensic Toxicologists |archive-url=https://web.archive.org/web/20150406202220/http://www.soft-tox.org/files/Designer_Drugs/Alpha-PVP.pdf |archive-date=April 6, 2015 }}</ref> α-PVP is chemically related to ] and is the ] ] of ].<ref>{{cite journal |vauthors=Sauer C, Peters FT, Haas C, Meyer MR, Fritschi G, Maurer HH |date=June 2009 |title=New designer drug alpha-pyrrolidinovalerophenone (PVP): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques |journal=Journal of Mass Spectrometry |volume=44 |issue=6 |pages=952–64 |bibcode=2009JMSp...44..952S |doi=10.1002/jms.1571 |pmid=19241365}}</ref> |
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Colloquially, it is sometimes called '''flakka''' or '''gravel'''.<ref>{{cite web|url=http://www.cbc.ca/news/canada/manitoba/zombie-drug-flakka-may-have-hit-winnipeg-streets-police-1.4383153|title='Zombie drug' flakka may have hit Winnipeg streets: police|work=]|date=November 2, 2017| vauthors = Coubrough J }}</ref><ref>{{cite web |url= https://www.independent.co.uk/news/world/americas/flakka-what-is-it-florida-face-eating-attack-zombie-drug-austin-harrouff-a7195871.html |archive-url=https://web.archive.org/web/20160818194424/http://www.independent.co.uk/news/world/americas/flakka-what-is-it-florida-face-eating-attack-zombie-drug-austin-harrouff-a7195871.html |archive-date=2016-08-18 |url-access=limited |url-status=live|title=Flakka: What is the 'zombie drug' blamed for face-eating attacks?|work=]|date=August 17, 2016| vauthors = England C, Garcia F }}</ref> |
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==See also== |
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<!--==Uses== |
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* ] |
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Fill in this subsection when there is more information. |
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* ] |
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===Recreational===--> |
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* ] |
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* ] |
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* ] |
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== Adverse effects == |
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==References== |
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α-PVP, like other stimulants, can cause hyperstimulation, ], and ].<ref>{{cite web| url = http://www.drugabuse.gov/drugs-abuse/emerging-trends| title = Drugs of Abuse Emerging Trends| publisher = National Institute on Drug Abuse| date = 6 April 2015}}</ref> α-PVP has been reported to be the cause, or a significant contributory cause of death in ] and ] caused by combinations of drugs.<ref>{{cite journal | vauthors = Marinetti LJ, Antonides HM | title = Analysis of synthetic cathinones commonly found in bath salts in human performance and postmortem toxicology: method development, drug distribution and interpretation of results | journal = Journal of Analytical Toxicology | volume = 37 | issue = 3 | pages = 135–46 | date = April 2013 | pmid = 23361867 | doi = 10.1093/jat/bks136 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Richards-Waugh LL, Bailey KM, Clay DJ, Gebhardt MA, Newsome-Sparks CL, Majmoud HE, Venuti SE, Kraner JC | date = 2013 | journal = AAFS Proceedings | id = Abstract K16 | title = t | url = http://www.aafs.org/sites/default/files/pdf/ProceedingsWashingtonDC2013.pdf | access-date = 2015-04-03 | archive-url = https://web.archive.org/web/20161108233911/http://www.aafs.org/sites/default/files/pdf/ProceedingsWashingtonDC2013.pdf | archive-date = 2016-11-08 }}</ref><ref>{{cite news | url = https://news.yahoo.com/cheap-synthetic-flakka-dethroning-cocaine-florida-drug-scene-140910992.html | quote = 27 people have died from flakka-related overdoses in the last eight months in Broward County | title = Cheap, synthetic 'flakka' dethroning cocaine on Florida drug scene }}</ref><ref>{{cite journal | vauthors = Klavž J, Gorenjak M, Marinšek M | title = Suicide attempt with a mix of synthetic cannabinoids and synthetic cathinones: Case report of non-fatal intoxication with AB-CHMINACA, AB-FUBINACA, alpha-PHP, alpha-PVP and 4-CMC | journal = Forensic Science International | volume = 265 | pages = 121–4 | date = August 2016 | pmid = 26890319 | doi = 10.1016/j.forsciint.2016.01.018 }}</ref> α-PVP has also been linked to at least one death with pulmonary edema and moderately advanced atherosclerotic coronary disease when it was combined with ].<ref>{{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 = }}</ref> |
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{{reflist}} |
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According to Craig Crespi in the journal '']'', "symptoms are known to easily escalate into frightening ]s, ] ], extreme ], and a multitude of other ]s." These common adverse effects of α-PVP are in line with other stimulants.{{cn|date=October 2024}} |
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In addition, ] has been named as an adverse effect of α-PVP.<ref name="Ma2016">{{cite journal | vauthors = Mash DC | title = Excited Delirium and Sudden Death: A Syndromal Disorder at the Extreme End of the Neuropsychiatric Continuum | journal = Frontiers in Physiology | volume = 7 | pages = 435 | date = 2016 | pmid = 27790150 | pmc = 5061757 | doi = 10.3389/fphys.2016.00435 | doi-access = free }}</ref> |
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== Pharmacology == |
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α-PVP acts as a ] (NDRI), similar to ] and ], with IC<sub>50</sub> values of 14.2 and 12.8 nM, respectively, similar to its ] derivative ].<ref name="EMCDDA">{{cite web | url=http://www.emcdda.europa.eu/publications/joint-reports/alpha-pvp | title=EMCDDA–Europol Joint Report on a new psychoactive substance: 1-phenyl-2-(1-pyrrolidinyl)-1-pentanone (α-PVP) | publisher=European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) | date=September 2015}}</ref><ref>{{cite journal | vauthors = Marusich JA, Antonazzo KR, Wiley JL, Blough BE, Partilla JS, Baumann MH | title = Pharmacology of novel synthetic stimulants structurally related to the "bath salts" constituent 3,4-methylenedioxypyrovalerone (MDPV) | journal = Neuropharmacology | volume = 87 | pages = 206–13 | date = December 2014 | pmid = 24594476 | pmc = 4152390 | doi = 10.1016/j.neuropharm.2014.02.016 }}</ref><ref>{{cite journal | vauthors = Rickli A, Hoener MC, Liechti ME | title = Monoamine transporter and receptor interaction profiles of novel psychoactive substances: para-halogenated amphetamines and pyrovalerone cathinones | journal = European Neuropsychopharmacology | volume = 25 | issue = 3 | pages = 365–76 | date = March 2015 | pmid = 25624004 | doi = 10.1016/j.euroneuro.2014.12.012 | s2cid = 5511568 | url = http://edoc.unibas.ch/56167/1/20170921162745_59c3cc617d4fd.pdf }}</ref><ref>{{cite journal | vauthors = Meltzer PC, Butler D, Deschamps JR, Madras BK | title = 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors | journal = Journal of Medicinal Chemistry | volume = 49 | issue = 4 | pages = 1420–32 | date = February 2006 | pmid = 16480278 | pmc = 2602954 | doi = 10.1021/jm050797a }}</ref> Similar to other ], α-PVP has been shown to have reinforcing effects in rats.<ref>{{cite journal | vauthors = Gannon BM, Galindo KI, Mesmin MP, Sulima A, Rice KC, Collins GT | title = Relative reinforcing effects of second-generation synthetic cathinones: Acquisition of self-administration and fixed ratio dose-response curves in rats | journal = Neuropharmacology | volume = 134 | issue = Pt A | pages = 28–35 | date = May 2018 | pmid = 28811192 | pmc = 5809320 | doi = 10.1016/j.neuropharm.2017.08.018 }}</ref><ref>{{cite journal | vauthors = Gannon BM, Rice KC, Collins GT | title = Reinforcing effects of abused 'bath salts' constituents 3,4-methylenedioxypyrovalerone and α-pyrrolidinopentiophenone and their enantiomers | journal = Behavioural Pharmacology | volume = 28 | issue = 7 | pages = 578–581 | date = October 2017 | pmid = 28570297 | pmc = 5599337 | doi = 10.1097/FBP.0000000000000315 }}</ref> |
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== Chemistry == |
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α-PVP gives no reaction with the ]. It gives a grey/black reaction with the ].<ref>{{cite web | url=http://reagent-base.net/reagents-table/ | title=Reactions table | publisher=Reagent Base | access-date=3 December 2015 | archive-url=https://web.archive.org/web/20151208180616/http://reagent-base.net/reagents-table/ | archive-date=2015-12-08 }}</ref> |
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=== Detection in body fluids === |
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α-PVP may be quantified in blood, plasma or urine by ] to confirm a diagnosis of poisoning in hospitalized patients or to provide evidence in a medicolegal death investigation. Blood or plasma α-PVP concentrations are expected to be in a range of 10–50 μg/L in persons using the drug recreationally, >100 μg/L in intoxicated patients and >300 μg/L in victims of acute overdosage.<ref>{{cite journal | vauthors = Eiden C, Mathieu O, Cathala P, Debruyne D, Baccino E, Petit P, Peyriere H | title = Toxicity and death following recreational use of 2-pyrrolidino valerophenone | journal = Clinical Toxicology | volume = 51 | issue = 9 | pages = 899–903 | date = November 2013 | pmid = 24111554 | doi = 10.3109/15563650.2013.847187 | s2cid = 22826544 }}</ref><ref>{{cite book | vauthors = Baselt RC | title = Disposition of toxic drugs and chemicals in man | year = 2014 | publisher = Biomedical Publications | location = Seal Beach, Ca. | isbn = 978-0-9626523-9-4 | page = 1751 }}</ref> |
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== Society and culture == |
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=== Legal status === |
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α-PVP is banned in Estonia, Finland, France, Germany, Hungary, Russia, Ireland, Latvia, Lithuania, Netherlands, Poland, Romania, Slovenia, Sweden, the United Kingdom, Turkey, Norway,<ref name="EMCDDA"/> as well as the Czech Republic.<ref>{{cite web | url=https://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf | title=Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.) | publisher=Ministerstvo zdravotnictví | archive-url=https://web.archive.org/web/20200515081621/https://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf | archive-date=2020-05-15 | language=cs}}</ref> |
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==== Australia ==== |
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α-PVP is a ] prohibited substance under the ] (July 2016).<ref name="Poisons Standard">Poisons Standard July 2016 </ref> A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.<ref name="Poisons Standard" /> The drug was explicitly made illegal in ] after it was illegally marketed with the imprimatur of erroneous legal advice that it was not encompassed by analog provisions of the relevant act. It is encompassed by those provisions, and therefore has been illegal for many years in New South Wales. The legislative action followed the death of two individuals from using it; one jumping off a balcony, another having a heart attack after a state of ].<ref name=OldingSydney>{{cite news | vauthors = Olding R | title = 'Bath salts' death: lethal drug was a top seller | url = http://www.smh.com.au/nsw/bath-salts-death-glenn-punchs-terrifying-end-20131008-2v5jp.html | work=The Sydney Morning Herald}}</ref><ref>{{cite web|url=http://bigstory.ap.org/article/f3667988d0e042cfbb9b40838a78ab65/naked-paranoids-begging-police-save-them-thats-flakka|title=Flakka, synthetic drug behind increasingly bizarre crimes|publisher=AP|date=30 Apr 2015|access-date=30 April 2015|archive-date=2 May 2015|archive-url=https://web.archive.org/web/20150502232931/http://bigstory.ap.org/article/f3667988d0e042cfbb9b40838a78ab65/naked-paranoids-begging-police-save-them-thats-flakka|url-status=dead}}</ref> |
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==== European Union ==== |
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α-PVP was required to be banned by EU member states by 3 July 2017.<ref>{{CELEX|id=32016D1070|text=Council Implementing Decision (EU) 2016/1070 of 27 June 2016 on subjecting 1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one (α-pyrrolidinovalerophenone, α-PVP) to control measures}}</ref> |
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==== China ==== |
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As of October 2015, α-PVP is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html |script-title=zh:关于印发《非药用类麻醉药品和精神药品列管办法》的通知 |website=China Food and Drug Administration | date=27 September 2015 | language=zh | 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 }}</ref> |
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==== Italy ==== |
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] and all structurally derived analogues (including ] analogues) were classified as narcotics in January 2012.<ref>{{cite web | url=http://www.politicheantidroga.it/media/491607/decreto%20ministero%20salute%2029%20dicembre%202011.pdf | title=Decreto 29 dicembre 2011 (12A00013) (G.U. Serie Generale n. 3 del 4 gennaio 2012) | access-date=2016-05-28 | archive-url=https://web.archive.org/web/20160701171219/http://www.politicheantidroga.it/media/491607/decreto%20ministero%20salute%2029%20dicembre%202011.pdf | archive-date=2016-07-01 }}</ref><ref name="EMCDDA"/> |
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==== United States ==== |
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On January 28, 2014, the U.S. ] (DEA) listed α-PVP, along with nine other synthetic ], as a ] controlled substance with a temporary ban, effective February 27, 2014.<ref>{{cite web |title=Rules - 2014 |website=DEA/DOJ Diversion Control |url=http://www.deadiversion.usdoj.gov/fed_regs/rules/2014/fr0128.htm |access-date=2014-02-01 |archive-date=2016-10-17 |archive-url=https://web.archive.org/web/20161017130614/https://www.deadiversion.usdoj.gov/fed_regs/rules/2014/fr0128.htm |url-status=dead }}</ref> The temporary ban was then extended.<ref>{{cite web |url=https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf |title= Lists of<nowiki>:</nowiki>Scheduling Actions, Controlled Substances, Regulated Chemicals|author=<!--Staff writer(s); no by-line.--> |date=August 2016|website=US Department of Justice |access-date= September 29, 2016}}</ref> |
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=== Economics === |
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α-PVP is sometimes the active ingredient in recreational drugs sold as "]".<ref name=OldingSydney/> It may also be distinguished from "bath salts" and sold under a different name: "flakka," a name used in Florida, or "gravel" in other parts of the U.S. It is reportedly available as cheaply as US$5 per dose.<ref>{{cite news| url=http://www.inc.com/joseph-steinberg/flakka-the-new-illegal-drug-you-need-to-know-about.html |work=Inc. | title=Flakka: The New Illegal Drug You Need to Know About | date=November 8, 2015 | access-date=November 11, 2015 | vauthors = Steinberg J }}</ref> A laboratory for one county in Florida reported a steady rise in α-PVP detections in seized drugs from none in January–February 2014 to 84 in September 2014.<ref name=Alvarez>{{cite news |url=http://www.sun-sentinel.com/local/broward/fl-flakka-on-the-rise-20150402-story.html |title=Flakka: Rampant designer drug dubbed '$5 insanity' |work=] |location=Fort Lauderdale, Fla. | vauthors = Alvarez T |date=April 2, 2015}}</ref> |
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== See also == |
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* ] (α-PHP) |
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* ] (α-PVT) |
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* ] |
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* ] |
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* ] |
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* ] (O-2482) |
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* ] |
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* ] |
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* ] |
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* ] (O-2371) |
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== References == |
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{{pharm-stub}} |
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{{reflist|30em}} |
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{{stimulants}} |
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{{Stimulants}} |
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{{DEFAULTSORT:Pyrrolidinopentiophenone, alpha-}} |
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{{DEFAULTSORT:Pyrrolidinopentiophenone, α-}} |
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