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| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
| PubChem =
| PubChem = 71721462
| ChemSpiderID = 29738196
| ChemSpiderID = 29738196
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1156792AA
| UNII = 6JA2K09914


<!--Chemical data-->
<!--Chemical data-->
| C=13 | H=19 | N=1 | O=1 | S=1
| C=13 | H=19 | N=1 | O=1 | S=1
| molecular_weight = 237.4 g/mol
| molecular_weight = 237.36 g/mol
| melting_point =
| melting_point =
| smiles = O=C(C(CCC)N1CCCC1)C2=CC=CS2.Cl
| smiles = CCCC(N1CCCC1)C(=O)c2sccc2
| StdInChI = 1S/C13H19NOS.ClH/c1-2-6-11(14-8-3-4-9-14)13(15)12-7-5-10-16-12;/h5,7,10-11H,2-4,6,8-9H2,1H3;1H
| StdInChI = 1S/C13H19NOS/c1-2-6-11(14-8-3-4-9-14)13(15)12-7-5-10-16-12/h5,7,10-11H,2-4,6,8-9H2,1H3
| StdInChIKey = RURGIWIREJBFLI-UHFFFAOYSA-N
| StdInChIKey = OOSRPGUQJAKBLV-UHFFFAOYSA-N

}}
}}


'''α-Pyrrolidinopentiothiophenone ''' (also known as '''α-PVT''') is a synthetic [[stimulant]] of the [[Substituted cathinone|cathinone]] class that has been sold online as a [[designer drug]].<ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/14182 | title=α-Pyrrolidinopentiothiophenone | publisher=Cayman Chemical | accessdate=29 June 2015}}</ref><ref>{{cite journal | url=http://www.sciencedirect.com/science/article/pii/S0021967315005270 | title=Simultaneous determination of 40 novel psychoactive stimulants in urine by liquid chromatography-high resolution mass spectrometry and library matching. |author1=Marta Concheiro |author2=Marisol Castaneto |author3=Robert Kronstrand |author4=Marilyn A. Huestis | journal=Journal of Chromatography A |date=June 2015 | volume=1397 | issue=5 | pages=32–42 | doi=10.1016/j.chroma.2015.04.002 | pmid=25931378}}</ref><ref>{{cite journal | url=http://link.springer.com/article/10.1007/s11419-015-0288-3 | title=Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products |author1=Takahiro Doi |author2=Akiko Asada |author3=Akihiro Takeda |author4=Takaomi Tagami |author5=Munehiro Katagi |author6=Shuntaro Matsuta |author7=Hiroe Kamata |author8=Masami Kawaguchi |author9=Yuka Satsuki |author10=Yoshiyuki Sawabe |author11=Hirotaka Obana | journal=Forensic Toxicology | date=January 2016 | volume=34 | issue=1 | pages=76-93 | doi=10.1007/s11419-015-0288-3}}</ref> It is a [[Structural analog|analogue]] of [[Alpha-Pyrrolidinopentiophenone|α-PVP]] where the [[Phenyl group|phenyl]] ring has been replaced by [[thiophene]].
'''α-Pyrrolidinopentiothiophenone ''' (also known as '''α-PVT''') is a synthetic [[stimulant]] of the [[Substituted cathinone|cathinone]] class that has been sold online as a [[designer drug]].<ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/14182 | title=α-Pyrrolidinopentiothiophenone | publisher=Cayman Chemical | accessdate=29 June 2015}}</ref><ref>{{cite journal | url=http://www.sciencedirect.com/science/article/pii/S0021967315005270 | title=Simultaneous determination of 40 novel psychoactive stimulants in urine by liquid chromatography-high resolution mass spectrometry and library matching. |author1=Marta Concheiro |author2=Marisol Castaneto |author3=Robert Kronstrand |author4=Marilyn A. Huestis | journal=Journal of Chromatography A |date=June 2015 | volume=1397 | issue=5 | pages=32–42 | doi=10.1016/j.chroma.2015.04.002 | pmid=25931378}}</ref><ref>{{cite journal | url=http://link.springer.com/article/10.1007/s11419-015-0288-3 | title=Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products |author1=Takahiro Doi |author2=Akiko Asada |author3=Akihiro Takeda |author4=Takaomi Tagami |author5=Munehiro Katagi |author6=Shuntaro Matsuta |author7=Hiroe Kamata |author8=Masami Kawaguchi |author9=Yuka Satsuki |author10=Yoshiyuki Sawabe |author11=Hirotaka Obana | journal=Forensic Toxicology | date=January 2016 | volume=34 | issue=1 | pages=76-93 | doi=10.1007/s11419-015-0288-3}}</ref> It is a [[Structural analog|analogue]] of [[Alpha-Pyrrolidinopentiophenone|α-PVP]] where the [[Phenyl group|phenyl]] ring has been replaced by [[thiophene]].


α-PVT was first identified in Japan in 2013.<ref>{{cite journal | url=http://link.springer.com/article/10.1007%2Fs11419-013-0182-9 | title=Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products |author1=Nahoko Uchiyama |author2=Satoru Matsuda |author3=Maiko Kawamura |author4=Ruri Kikura-Hanajiri |author5=Yukihiro Goda | journal=Forensic Toxicology |date=July 2013 | volume=31 | issue=2 | pages=223–240 | doi=10.1007/s11419-013-0182-9}}</ref> Its metabolism has been described in literature.<ref>{{cite journal | url=http://onlinelibrary.wiley.com/doi/10.1002/bmc.3155/abstract | title=UPLC/ESI-MS/MS-based determination of metabolism of several new illicit drugs, ADB-FUBINACA, AB-FUBINACA, AB-PINACA, QUPIC, 5F-QUPIC and α-PVT, by human liver microsome. |author1=Takahiro Takayama |author2=Mayu Suzuki |author3=Kenichiro Todoroki |author4=Koichi Inoue |author5=Jun Zhe Min |author6=Ruri Kikura-Hanajiri |author7=Yukihiro Goda |author8=Toshimasa Toyo'oka | journal=Biomedical Chromatography |date=June 2014 | volume=28 | issue=6 | pages=831–838 | doi=10.1002/bmc.3155 | pmid=24861751}}</ref><ref>{{cite journal | url=http://www.future-science.com/doi/10.4155/bio.15.237 | title=In vitro, in vivo and in silico metabolic profiling of α-pyrrolidinopentiothiophenone, a novel thiophene stimulant |author1=Madeleine J Swortwood |author2=Jeremy Carlier |author3=Kayla N Ellefsen |author4=Ariane Wohlfarth |author5=Xingxing Diao |author6=Marta Concheiro-Guisan |author7=Robert Kronstrand |author8=Marilyn A Huestis | journal=Bioanalysis | date=December 2015 | doi=10.4155/bio.15.237 | pmid=26648097}}</ref>
α-PVT was first identified in Japan in 2013.<ref>{{cite journal | url=http://link.springer.com/article/10.1007%2Fs11419-013-0182-9 | title=Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products |author1=Nahoko Uchiyama |author2=Satoru Matsuda |author3=Maiko Kawamura |author4=Ruri Kikura-Hanajiri |author5=Yukihiro Goda | journal=Forensic Toxicology |date=July 2013 | volume=31 | issue=2 | pages=223–240 | doi=10.1007/s11419-013-0182-9}}</ref> Its metabolism has been described in literature.<ref>{{cite journal | url=http://onlinelibrary.wiley.com/doi/10.1002/bmc.3155/abstract | title=UPLC/ESI-MS/MS-based determination of metabolism of several new illicit drugs, ADB-FUBINACA, AB-FUBINACA, AB-PINACA, QUPIC, 5F-QUPIC and α-PVT, by human liver microsome. |author1=Takahiro Takayama |author2=Mayu Suzuki |author3=Kenichiro Todoroki |author4=Koichi Inoue |author5=Jun Zhe Min |author6=Ruri Kikura-Hanajiri |author7=Yukihiro Goda |author8=Toshimasa Toyo'oka | journal=Biomedical Chromatography |date=June 2014 | volume=28 | issue=6 | pages=831–838 | doi=10.1002/bmc.3155 | pmid=24861751}}</ref><ref>{{cite journal | author1=Madeleine J. Swortwood | url=http://www.future-science.com/doi/10.4155/bio.15.237 | title=In vitro, in vivo and in silico metabolic profiling of α-pyrrolidinopentiothiophenone, a novel thiophene stimulant | date=January 2016 | author2=Jeremy Carlier | author3=Kayla N. Ellefsen | author4=Ariane Wohlfarth | author5=Xingxing Diao | author6=Marta Concheiro-Guisan | author7=Robert Kronstrand | author8=Marilyn A. Huestis | journal=Bioanalysis | volume=8 | issue=1 | pages=65–82 | doi=10.4155/bio.15.237 | pmid=26648097}}</ref>

==Side effects==

α-PVT has been shown to possess high [[cytotoxicity]] against human cell lines.<ref>{{cite journal | url=http://link.springer.com/article/10.1007%2Fs12640-016-9640-6 | title=Cytotoxic Activity of Pyrovalerone Derivatives, an Emerging Group of Psychostimulant Designer Cathinones | author1=Jakub Wojcieszak | author2=Dariusz Andrzejczak | author3=Agata Woldan-Tambor | author4=Jolanta B. Zawilska | journal=Neurotoxicity Research | date=June 2016 | pages=1–12 | doi=10.1007/s12640-016-9640-6 | pmid=27295059}}</ref>


==Legality==
==Legality==

Revision as of 03:58, 16 June 2016

alpha-Pyrrolidinopentiothiophenone
Legal status
Legal status
  • UK: Class B
  • Illegal in China, Sweden and Switzerland
Identifiers
  • 2-(pyrrolidin-1-yl)-1-(thiophen-2-yl)pentan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H19NOS
Molar mass237.36 g/mol g·mol−1
3D model (JSmol)
  • CCCC(N1CCCC1)C(=O)c2sccc2
  • InChI=1S/C13H19NOS/c1-2-6-11(14-8-3-4-9-14)13(15)12-7-5-10-16-12/h5,7,10-11H,2-4,6,8-9H2,1H3
  • Key:OOSRPGUQJAKBLV-UHFFFAOYSA-N

α-Pyrrolidinopentiothiophenone (also known as α-PVT) is a synthetic stimulant of the cathinone class that has been sold online as a designer drug.[1][2][3] It is a analogue of α-PVP where the phenyl ring has been replaced by thiophene.

α-PVT was first identified in Japan in 2013.[4] Its metabolism has been described in literature.[5][6]

Side effects

α-PVT has been shown to possess high cytotoxicity against human cell lines.[7]

Legality

Sweden's public health agency suggested classifying α-PVT as hazardous substance on November 10, 2014.[8]

As of October 2015 α-PVT is a controlled substance in China.[9]

α-PVT is illegal in Switzerland as of December 2015.[10]

See also

References

  1. ^ "α-Pyrrolidinopentiothiophenone". Cayman Chemical. Retrieved 29 June 2015.
  2. ^ Marta Concheiro; Marisol Castaneto; Robert Kronstrand; Marilyn A. Huestis (June 2015). "Simultaneous determination of 40 novel psychoactive stimulants in urine by liquid chromatography-high resolution mass spectrometry and library matching". Journal of Chromatography A. 1397 (5): 32–42. doi:10.1016/j.chroma.2015.04.002. PMID 25931378.
  3. ^ Takahiro Doi; Akiko Asada; Akihiro Takeda; Takaomi Tagami; Munehiro Katagi; Shuntaro Matsuta; Hiroe Kamata; Masami Kawaguchi; Yuka Satsuki; Yoshiyuki Sawabe; Hirotaka Obana (January 2016). "Identification and characterization of α-PVT, α-PBT, and their bromothienyl analogs found in illicit drug products". Forensic Toxicology. 34 (1): 76–93. doi:10.1007/s11419-015-0288-3.
  4. ^ Nahoko Uchiyama; Satoru Matsuda; Maiko Kawamura; Ruri Kikura-Hanajiri; Yukihiro Goda (July 2013). "Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products". Forensic Toxicology. 31 (2): 223–240. doi:10.1007/s11419-013-0182-9.
  5. ^ Takahiro Takayama; Mayu Suzuki; Kenichiro Todoroki; Koichi Inoue; Jun Zhe Min; Ruri Kikura-Hanajiri; Yukihiro Goda; Toshimasa Toyo'oka (June 2014). "UPLC/ESI-MS/MS-based determination of metabolism of several new illicit drugs, ADB-FUBINACA, AB-FUBINACA, AB-PINACA, QUPIC, 5F-QUPIC and α-PVT, by human liver microsome". Biomedical Chromatography. 28 (6): 831–838. doi:10.1002/bmc.3155. PMID 24861751.
  6. ^ Madeleine J. Swortwood; Jeremy Carlier; Kayla N. Ellefsen; Ariane Wohlfarth; Xingxing Diao; Marta Concheiro-Guisan; Robert Kronstrand; Marilyn A. Huestis (January 2016). "In vitro, in vivo and in silico metabolic profiling of α-pyrrolidinopentiothiophenone, a novel thiophene stimulant". Bioanalysis. 8 (1): 65–82. doi:10.4155/bio.15.237. PMID 26648097.
  7. ^ Jakub Wojcieszak; Dariusz Andrzejczak; Agata Woldan-Tambor; Jolanta B. Zawilska (June 2016). "Cytotoxic Activity of Pyrovalerone Derivatives, an Emerging Group of Psychostimulant Designer Cathinones". Neurotoxicity Research: 1–12. doi:10.1007/s12640-016-9640-6. PMID 27295059.
  8. ^ "Cannabinoider föreslås bli klassade som hälsofarlig vara" (in Swedish). Retrieved 29 June 2015.
  9. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
  10. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.


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