From Wikipedia, the free encyclopedia
Chemical compound
5F-MDMB-PICA
Other names 5F-MDMB-2201; 5-Fluoro MDMB-PICA
Legal status
Methyl (2S )-2-[[1-(5-fluoropentyl)indole-3-carbonyl]amino]-3,3-dimethylbutanoate
CAS Number
PubChem
CID
ChemSpider
UNII
KEGG
Formula C 21 H 29 F N 2 O 3
Molar mass 376.472 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 (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
^
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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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.
doi :
10.1007/s00204-022-03332-z .
PMC
9352624 .
PMID
35788413 .
^
"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 .
^ 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 .
^
"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.
^
"December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling" .
^
"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
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comparison )
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Allosteric
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