5F-MDMB-PICA

5F-MDMB-PICA

Clinical data
Other names	5F-MDMB-2201; 5-Fluoro MDMB-PICA
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics) [1] CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I UN: Psychotropic Schedule II
Identifiers
IUPAC name Methyl (2S)-2-[[1-(5-fluoropentyl)indole-3-carbonyl]amino]-3,3-dimethylbutanoate
CAS Number	1971007-88-1
PubChem CID	129597835
ChemSpider	68003951
UNII	NG3U6O970A
KEGG	C22803
Chemical and physical data
Formula	C21H29FN2O3
Molar mass	376.472 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=CN(CCCCCF)C2=C1C=CC=C2
InChI 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 (MDMB-5F-PICA ^[2] ) is a designer drug and synthetic cannabinoid. ^{[3] [4] [5] [6] [7]} In 2018, it was the fifth-most common synthetic cannabinoid identified in drugs seized by the Drug Enforcement Administration. ^[8]

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. ^[9]

In the United States, 5F-MDMB-PICA was temporarily emergency scheduled by the DEA in 2019. ^[10] In December 2019, the UNODC announced scheduling recommendations placing 5F-MDMB-PICA into Schedule II. ^[11] In the United States 5F-MDMB-PICA was made a permanent Schedule I Controlled Substance nationwide on April 7, 2022. ^[12]

References

1. Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
2. Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID   36346325. S2CID   253396419.
3. 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.
4. 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.
5. Szpot P, Nowak K, Wachełko O, Tusiewicz K, Chłopaś-Konowałek A, Zawadzki M (January 2023). "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. 41 (1): 47–58. doi:10.1007/s11419-022-00629-7. PMID   36652054. S2CID   249318941.
6. Tokarczyk B, Jurczyk A, Krupińska J, Adamowicz P (December 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. 18 (4): 393–402. doi:10.1007/s12024-022-00492-3. PMC   9194349 . PMID   35699867.
7. Wagmann L, Stiller RG, Fischmann S, Westphal F, Meyer MR (October 2022). "Going deeper into the toxicokinetics of synthetic cannabinoids: in vitro contribution of human carboxylesterases". Archives of Toxicology. 96 (10): 2755–2766. Bibcode:2022ArTox..96.2755W. doi:10.1007/s00204-022-03332-z. PMC   9352624 . PMID   35788413.
8. "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.
9. 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): 1241–1254. doi:10.1021/acschemneuro.6b00137. PMID   27421060.
10. "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.
11. "December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling".
12. "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

• Musa A, Simola N, Piras G, Caria F, Onaivi ES, De Luca MA (December 2020). "Neurochemical and Behavioral Characterization after Acute and Repeated Exposure to Novel Synthetic Cannabinoid Agonist 5-MDMB-PICA". Brain Sciences. 10 (12): 1011. doi: 10.3390/brainsci10121011 . PMC   7766979 . PMID   33353194.