alpha-Pyrrolidinopentiothiophenone

α-Pyrro​lidino​pentio​thiophenone (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class that has been sold online as a designer drug.[1][2][3] It is an analogue of α-PVP where the phenyl ring has been replaced by thiophene.

alpha-Pyrrolidinopentiothiophenone

Legal status
Legal status	DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B Illegal in China, Sweden and Switzerland
Identifiers
IUPAC name 2-(Pyrrolidin-1-yl)-1-(thiophen-2-yl)pentan-1-one
CAS Number	1400742-66-6
PubChem CID	71721462
ChemSpider	29738196
UNII	6JA2K09914
CompTox Dashboard (EPA)	DTXSID90857020
Chemical and physical data
Formula	C13H19NOS
Molar mass	237.36 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCCC(N1CCCC1)C(=O)c2sccc2
InChI 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-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

• α-Pyrrolidinopropiophenone (α-PPP)
• α-Pyrrolidinobutiophenone (α-PBP)
• α-Pyrrolidinohexiophenone (α-PHP)
• Methiopropamine
• Naphyrone (O-2482)
• Pyrovalerone (O-2371)
• Thiopropamine
• Thiothinone

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. PMC 4433760. 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. PMC 5493968. 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. 30 (2): 239–50. 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. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
10. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.