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Wikipedia

5F-APINACA

April 30, 2023

Not to be confused with 5F-AB-PINACA.

5F-APINACA (also known as 5F-AKB-48 or 5F-AKB48) is an indazole-based synthetic cannabinoid that has been sold online as a designer drug.[1][2] Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with a 5-fluoropentyl chain on the indazole 1-position, and 5F-APINACA falls within the claims of this patent, as despite not being disclosed as an example, it is very similar to the corresponding pentanenitrile and 4-chlorobutyl compounds which are claimed as examples 3 and 4.[3]

5F-APINACA
Clinical data
Other names5F-AKB-48, 5F-AKB48
Legal status
Legal status
Identifiers
  • N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide
CAS Number
  • 1400742-13-3
PubChem CID
  • 71711119
ChemSpider
  • 29339965
UNII
  • TX64ZY5P0R
CompTox Dashboard (EPA)
  • DTXSID80856800
Chemical and physical data
FormulaC23H30FN3O
Molar mass383.511 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C(NC1(C[C@@H]2C3)C[C@H](C2)C[C@H]3C1)C4=NN(CCCCCF)C5=CC=CC=C54
  • InChI=1S/C23H30FN3O/c24-8-4-1-5-9-27-20-7-3-2-6-19(20)21(26-27)22(28)25-23-13-16-10-17(14-23)12-18(11-16)15-23/h2-3,6-7,16-18H,1,4-5,8-15H2,(H,25,28)/t16-,17+,18-,23?
  • Key:UCMFSGVIEPXYIV-XHICYHHKSA-N

5F-APINACA was first identified in South Korea.[4] It is expected to be a potent agonist of the CB1 receptor and CB2 receptor.[5] Its metabolism has been described in literature.[6][7][8][9]

Pharmacology

5F-APINACA acts as a full agonist with a binding affinity of 1.94 nM at CB1 and 0.266 nM at CB2 cannabinoid receptors.[10]

Legality

In the United States, 5F-APINACA is a Schedule I controlled substance.[11]

5F-APINACA is an Anlage II controlled drug in Germany since July 2013.

As of October 2015, 5F-APINACA is a controlled substance in China.[12]

5F-APINACA is banned in the Czech Republic.[13]

See also

References

  1. ^ "AKB48 N-(5-fluoropentyl) analog". Cayman Chemical. Retrieved 6 July 2015.
  2. ^ "5F-AKB48" (PDF). Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG). 18 February 2013. Retrieved 6 July 2015.
  3. ^ WO 2003/035005
  4. ^ Chung H, Choi H, Heo S, Kim E, Lee J (January 2014). "Synthetic cannabinoids abused in South Korea: drug identifications by the National Forensic Service from 2009 to June 2013". Forensic Toxicology. 32 (1): 82–88. doi:10.1007/s11419-013-0213-6. S2CID 23058813.
  5. ^ "AKB48 (APINACA) and 5F-AKB48 (5F-APINACA)" (PDF). Drug Enforcement Administration. May 2013. Retrieved 6 July 2015.
  6. ^ Jang M, Shin I, Kim J, Yang W (February 2015). "Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry". Forensic Toxicology. 33 (2): 221–234. doi:10.1007/s11419-015-0265-x. S2CID 3038555.
  7. ^ Karinen R, Tuv SS, Øiestad EL, Vindenes V (January 2015). "Concentrations of APINACA, 5F-APINACA, UR-144 and its degradant product in blood samples from six impaired drivers compared to previous reported concentrations of other synthetic cannabinoids". Forensic Science International. 246: 98–103. doi:10.1016/j.forsciint.2014.11.012. PMID 25485949.
  8. ^ Holm NB, Pedersen AJ, Dalsgaard PW, Linnet K (March 2015). "Metabolites of 5F-AKB-48, a synthetic cannabinoid receptor agonist, identified in human urine and liver microsomal preparations using liquid chromatography high-resolution mass spectrometry". Drug Testing and Analysis. 7 (3): 199–206. doi:10.1002/dta.1663. PMID 24802286.
  9. ^ Wohlfarth A, Castaneto MS, Zhu M, Pang S, Scheidweiler KB, Kronstrand R, Huestis MA (May 2015). "Pentylindole/Pentylindazole Synthetic Cannabinoids and Their 5-Fluoro Analogs Produce Different Primary Metabolites: Metabolite Profiling for AB-PINACA and 5F-AB-PINACA". The AAPS Journal. 17 (3): 660–77. doi:10.1208/s12248-015-9721-0. PMC 4406957. PMID 25721194.
  10. ^ Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE (1 July 2016). "Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice". Forensic Toxicology. 34 (2): 329–343. doi:10.1007/s11419-016-0320-2. PMC 4929166. PMID 27429655.
  11. ^ "Schedules of Controlled Substances: Temporary Placement of Six Synthetic Cannabinoids (5F-ADB, 5F-AMB, 5F-APINACA, ADB-FUBINACA, MDMB-CHMICA and MDMB-FUBINACA) Into Schedule I". Drug Enforcement Administration.
  12. ^ (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  13. ^ "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví.

External links

  • Abouchedid R, Ho JH, Hudson S, Dines A, Archer JR, Wood DM, Dargan PI (December 2016). "Acute Toxicity Associated with Use of 5F-Derivations of Synthetic Cannabinoid Receptor Agonists with Analytical Confirmation". Journal of Medical Toxicology. 12 (4): 396–401. doi:10.1007/s13181-016-0571-7. PMC 5135680. PMID 27456262.

April 30, 2023
apinaca, confused, with, pinaca, also, known, akb48, indazole, based, synthetic, cannabinoid, that, been, sold, online, designer, drug, structurally, closely, resembles, cannabinoid, compounds, from, patent, 2003, 035005, with, fluoropentyl, chain, indazole, p. Not to be confused with 5F AB PINACA 5F APINACA also known as 5F AKB 48 or 5F AKB48 is an indazole based synthetic cannabinoid that has been sold online as a designer drug 1 2 Structurally it closely resembles cannabinoid compounds from patent WO 2003 035005 but with a 5 fluoropentyl chain on the indazole 1 position and 5F APINACA falls within the claims of this patent as despite not being disclosed as an example it is very similar to the corresponding pentanenitrile and 4 chlorobutyl compounds which are claimed as examples 3 and 4 3 5F APINACAClinical dataOther names5F AKB 48 5F AKB48Legal statusLegal statusCA Schedule II DE Anlage II Authorized trade only not prescriptible UK Class B US Schedule IIdentifiersIUPAC name N adamantan 1 yl 1 5 fluoropentyl 1H indazole 3 carboxamideCAS Number1400742 13 3PubChem CID71711119ChemSpider29339965UNIITX64ZY5P0RCompTox Dashboard EPA DTXSID80856800Chemical and physical dataFormulaC 23H 30F N 3OMolar mass383 511 g mol 13D model JSmol Interactive imageSMILES O C NC1 C C H 2C3 C C H C2 C C H 3C1 C4 NN CCCCCF C5 CC CC C54InChI InChI 1S C23H30FN3O c24 8 4 1 5 9 27 20 7 3 2 6 19 20 21 26 27 22 28 25 23 13 16 10 17 14 23 12 18 11 16 15 23 h2 3 6 7 16 18H 1 4 5 8 15H2 H 25 28 t16 17 18 23 Key UCMFSGVIEPXYIV XHICYHHKSA N5F APINACA was first identified in South Korea 4 It is expected to be a potent agonist of the CB1 receptor and CB2 receptor 5 Its metabolism has been described in literature 6 7 8 9 Contents 1 Pharmacology 2 Legality 3 See also 4 References 5 External linksPharmacology Edit5F APINACA acts as a full agonist with a binding affinity of 1 94 nM at CB1 and 0 266 nM at CB2 cannabinoid receptors 10 Legality EditIn the United States 5F APINACA is a Schedule I controlled substance 11 5F APINACA is an Anlage II controlled drug in Germany since July 2013 As of October 2015 5F APINACA is a controlled substance in China 12 5F APINACA is banned in the Czech Republic 13 See also Edit5F ADB 5F AMB AB FUBINACA AB CHFUPYCA AB PINACA ADB CHMINACA ADB FUBINACA ADB PINACA ADBICA APICA APINACA FUB APINACA MDMB CHMICA PX 3References Edit AKB48 N 5 fluoropentyl analog Cayman Chemical Retrieved 6 July 2015 5F AKB48 PDF Scientific Working Group for the Analysis of Seized Drugs SWGDRUG 18 February 2013 Retrieved 6 July 2015 WO 2003 035005 Chung H Choi H Heo S Kim E Lee J January 2014 Synthetic cannabinoids abused in South Korea drug identifications by the National Forensic Service from 2009 to June 2013 Forensic Toxicology 32 1 82 88 doi 10 1007 s11419 013 0213 6 S2CID 23058813 AKB48 APINACA and 5F AKB48 5F APINACA PDF Drug Enforcement Administration May 2013 Retrieved 6 July 2015 Jang M Shin I Kim J Yang W February 2015 Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography tandem mass spectrometry Forensic Toxicology 33 2 221 234 doi 10 1007 s11419 015 0265 x S2CID 3038555 Karinen R Tuv SS Oiestad EL Vindenes V January 2015 Concentrations of APINACA 5F APINACA UR 144 and its degradant product in blood samples from six impaired drivers compared to previous reported concentrations of other synthetic cannabinoids Forensic Science International 246 98 103 doi 10 1016 j forsciint 2014 11 012 PMID 25485949 Holm NB Pedersen AJ Dalsgaard PW Linnet K March 2015 Metabolites of 5F AKB 48 a synthetic cannabinoid receptor agonist identified in human urine and liver microsomal preparations using liquid chromatography high resolution mass spectrometry Drug Testing and Analysis 7 3 199 206 doi 10 1002 dta 1663 PMID 24802286 Wohlfarth A Castaneto MS Zhu M Pang S Scheidweiler KB Kronstrand R Huestis MA May 2015 Pentylindole Pentylindazole Synthetic Cannabinoids and Their 5 Fluoro Analogs Produce Different Primary Metabolites Metabolite Profiling for AB PINACA and 5F AB PINACA The AAPS Journal 17 3 660 77 doi 10 1208 s12248 015 9721 0 PMC 4406957 PMID 25721194 Hess C Schoeder CT Pillaiyar T Madea B Muller CE 1 July 2016 Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice Forensic Toxicology 34 2 329 343 doi 10 1007 s11419 016 0320 2 PMC 4929166 PMID 27429655 Schedules of Controlled Substances Temporary Placement of Six Synthetic Cannabinoids 5F ADB 5F AMB 5F APINACA ADB FUBINACA MDMB CHMICA and MDMB FUBINACA Into Schedule I Drug Enforcement Administration 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 Latky o ktere byl doplnen seznam c 4 psychotropnich latek priloha c 4 k narizeni vlady c 463 2013 Sb PDF in Czech Ministerstvo zdravotnictvi External links EditAbouchedid R Ho JH Hudson S Dines A Archer JR Wood DM Dargan PI December 2016 Acute Toxicity Associated with Use of 5F Derivations of Synthetic Cannabinoid Receptor Agonists with Analytical Confirmation Journal of Medical Toxicology 12 4 396 401 doi 10 1007 s13181 016 0571 7 PMC 5135680 PMID 27456262 Retrieved from https en wikipedia org w index php title 5F APINACA amp oldid 1086238074, wikipedia, wiki, book, books, library,

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