α-Pyrrolidinopentiothiophenone

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class that has been sold online as a designer drug.^[1]^[2]^[3] It is an analogue of α-PVP where the phenyl ring has been replaced by thiophene.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

It produces stimulating effects in humans, according to the individuals who have tried it. Most of the individuals who have tried it prefer α-PVP and α-PPP to it.

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^[update] α-PVT is a controlled substance in China.^[9]

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

References

^ "α-Pyrrolidinopentiothiophenone". Cayman Chemical. Retrieved 29 June 2015.
^ Concheiro M, Castaneto M, Kronstrand R, Huestis MA (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.
^ Doi T, Asada A, Takeda A, Tagami T, Katagi M, Matsuta S, et al. (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. S2CID 24528511.
^ Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (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. S2CID 1279637.
^ Takayama T, Suzuki M, Todoroki K, Inoue K, Min JZ, Kikura-Hanajiri R, et al. (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.
^ Swortwood MJ, Carlier J, Ellefsen KN, Wohlfarth A, Diao X, Concheiro-Guisan M, et al. (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.
^ Wojcieszak J, Andrzejczak D, Woldan-Tambor A, Zawilska JB (August 2016). "Cytotoxic Activity of Pyrovalerone Derivatives, an Emerging Group of Psychostimulant Designer Cathinones". Neurotoxicity Research. 30 (2): 239–250. doi:10.1007/s12640-016-9640-6. PMID 27295059. S2CID 11202107.
^ "Cannabinoider föreslås bli klassade som hälsofarlig vara" (in Swedish). Retrieved 29 June 2015.
^ "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.
^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.

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[1] "α-Pyrrolidinopentiothiophenone". Cayman Chemical. Retrieved 29 June 2015.

[2] Concheiro M, Castaneto M, Kronstrand R, Huestis MA (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] Doi T, Asada A, Takeda A, Tagami T, Katagi M, Matsuta S, et al. (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. S2CID 24528511.

[4] Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (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. S2CID 1279637.

[5] Takayama T, Suzuki M, Todoroki K, Inoue K, Min JZ, Kikura-Hanajiri R, et al. (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] Swortwood MJ, Carlier J, Ellefsen KN, Wohlfarth A, Diao X, Concheiro-Guisan M, et al. (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] Wojcieszak J, Andrzejczak D, Woldan-Tambor A, Zawilska JB (August 2016). "Cytotoxic Activity of Pyrovalerone Derivatives, an Emerging Group of Psychostimulant Designer Cathinones". Neurotoxicity Research. 30 (2): 239–250. doi:10.1007/s12640-016-9640-6. PMID 27295059. S2CID 11202107.

[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.

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α-Pyrrolidinopentiothiophenone

Contents

Side effects

Legality

See also

References