5F-MDMB-PICA
5F-MDMB-PICA.svg
Clinical data
Other names5F-MDMB-2201; 5-Fluoro MDMB-PICA
Legal status
Legal status
Identifiers
  • Methyl (2S)-2-[[1-(5-fluoropentyl)indole-3-carbonyl]amino]-3,3-dimethylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H29FN2O3
Molar mass376.472 g·mol−1
3D model (JSmol)
  • O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=CN(CCCCCF)C2=C1C=CC=C2
  • InChI=1S/C21H29FN2O3/c1-21(2,3)18(20(26)27-4)23-19(25)16-14-24(13-9-5-8-12-22)17-11-7-6-10-15(16)17/h6-7,10-11,14,18H,5,8-9,12-13H2,1-4H3,(H,23,25)/t18-/m1/s1
  • Key:CHSUEEBESACQDV-GOSISDBHSA-N

5F-MDMB-PICA is a designer drug and synthetic cannabinoid.[1][2][3][4][5] In 2018, it was the fifth-most common synthetic cannabinoid identified in drugs seized by the Drug Enforcement Administration.[6]

5F-MDMB-PICA is a potent agonist of both the CB1 receptor and the CB2 receptor with EC50 values of 0.45 nM and 7.4 nM, respectively.[7]

In the United States, 5F-MDMB-PICA was temporarily emergency scheduled by the DEA in 2019.[8] In December 2019, the UNODC announced scheduling recommendations placing 5F-MDMB-PICA into Schedule II.[9] In the United States 5F-MDMB-PICA was made a permanent Schedule I Controlled Substance nationwide on April 7, 2022.[10]

References

  1. ^ Risseeuw MD, Blanckaert P, Coopman V, Van Quekelberghe S, Van Calenbergh S, Cordonnier J (April 2017). "Identification of a new tert-leucinate class synthetic cannabinoid in powder and "spice-like" herbal incenses: Methyl 2-[[1-(5-fluoropentyl)indole-3-carbonyl]amino]-3,3-dimethyl-butanoate (5F-MDMB-PICA)". Forensic Science International. 273: 45–52. doi:10.1016/j.forsciint.2017.01.023. hdl:1854/LU-8542830. PMID 28214755.
  2. ^ Mogler L, Franz F, Rentsch D, Angerer V, Weinfurtner G, Longworth M, et al. (January 2018). "Detection of the recently emerged synthetic cannabinoid 5F-MDMB-PICA in 'legal high' products and human urine samples". Drug Testing and Analysis. 10 (1): 196–205. doi:10.1002/dta.2201. PMID 28371476.
  3. ^ Szpot, Paweł; Nowak, Karolina; Wachełko, Olga; Tusiewicz, Kaja; Chłopaś-Konowałek, Agnieszka; Zawadzki, Marcin (June 2022). "Methyl (S)-2-(1–7 (5-fluoropentyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate (5F-MDMB-PICA) intoxication in a child with identification of two new metabolites (ultra-high-performance liquid chromatography–tandem mass spectrometry)". Forensic Toxicology. doi:10.1007/s11419-022-00629-7. ISSN 1860-8973.
  4. ^ Tokarczyk, Bogdan; Jurczyk, Agnieszka; Krupińska, Justyna; Adamowicz, Piotr (June 2022). "Fatal intoxication with new synthetic cannabinoids 5F-MDMB-PICA and 4F-MDMB-BINACA—parent compounds and metabolite identification in blood, urine and cerebrospinal fluid". Forensic Science, Medicine and Pathology. doi:10.1007/s12024-022-00492-3. ISSN 1556-2891. PMID 35699867.
  5. ^ Wagmann, Lea; Stiller, Rebecca G.; Fischmann, Svenja; Westphal, Folker; Meyer, Markus R. (July 2022). "Going deeper into the toxicokinetics of synthetic cannabinoids: in vitro contribution of human carboxylesterases". Archives of Toxicology. doi:10.1007/s00204-022-03332-z. ISSN 1432-0738. PMID 35788413.
  6. ^ "Emerging Threat Report: Annual 2018" (PDF). Special Testing and Research Laboratory, Drug Enforcement Administration. Archived from the original (PDF) on 2019-08-01. Retrieved 2019-08-02.
  7. ^ Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, et al. (September 2016). "Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues". ACS Chemical Neuroscience. 7 (9): 1241–54. doi:10.1021/acschemneuro.6b00137. PMID 27421060.
  8. ^ "Schedules of Controlled Substances: Temporary Placement of 5F-EDMB-PINACA, 5F-MDMB-PICA, FUB-AKB48, 5F-CUMYL-PINACA, and FUB-144 into Schedule I". Federal Register. 2019-04-16.
  9. ^ "December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling".
  10. ^ "Schedules of Controlled Substances: Placement of 5F-EDMB-PINACA, 5FMDMB-PICA, FUB-AKB48, 5F-CUMYLPINACA, and FUB-144 in Schedule I" (PDF). Federal Register. 87 (67). 2022-04-07.

Further reading