5F-MDMB-PICA

{{Short description|Chemical compound}}

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{{Infobox drug

| drug_name =

| INN =

| type =

| IUPAC_name = Methyl (2S)-2-[[1-(5-fluoropentyl)indole-3-carbonyl]amino]-3,3-dimethylbutanoate

| image = 5F-MDMB-PICA.svg

| width = 120

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| legal_AU =

| legal_AU_comment =

| legal_BR = F2

| legal_BR_comment = {{cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_CA = Schedule II

| legal_DE = Anlage II

| legal_NZ =

| legal_UK = Class B

| legal_US = Schedule I

| legal_UN = P II

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| CAS_number = 1971007-88-1

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| PubChem = 129597835

| DrugBank =

| KEGG = C22803

| UNII = NG3U6O970A

| ChemSpiderID = 68003951

| synonyms = 5F-MDMB-2201; 5-Fluoro MDMB-PICA

| C=21|H=29|F=1|N=2|O=3

| smiles = O=C(N[C@H](C(OC)=O)C(C)(C)C)C1=CN(CCCCCF)C2=C1C=CC=C2

| StdInChI=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

| StdInChIKey = CHSUEEBESACQDV-GOSISDBHSA-N

}}

5F-MDMB-PICA (MDMB-5F-PICA{{cite journal | vauthors = Pulver B, Fischmann S, Gallegos A, Christie R | title = EMCDDA framework and practical guidance for naming synthetic cannabinoids | journal = Drug Testing and Analysis | volume = 15 | issue = 3 | pages = 255–276 | date = March 2023 | pmid = 36346325 | doi = 10.1002/dta.3403 | s2cid = 253396419 }}) is a designer drug and synthetic cannabinoid.{{cite journal | vauthors = Risseeuw MD, Blanckaert P, Coopman V, Van Quekelberghe S, Van Calenbergh S, Cordonnier J | title = 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) .{{cite web | url = https://ndews.umd.edu/sites/ndews.umd.edu/files/Emerging-Threat-Report-2018-Annual.pdf | title = Emerging Threat Report: Annual 2018 | publisher = Special Testing and Research Laboratory, Drug Enforcement Administration | access-date = 2019-08-02 | archive-date = 2019-08-01 | archive-url = https://web.archive.org/web/20190801190403/https://ndews.umd.edu/sites/ndews.umd.edu/files/Emerging-Threat-Report-2018-Annual.pdf | url-status = dead }}

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.{{cite journal | vauthors = Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, Mack JB, Glass M, McGregor IS, Connor M, Kassiou M | title = Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues | journal = ACS Chemical Neuroscience | volume = 7 | issue = 9 | pages = 1241–1254 | date = September 2016 | pmid = 27421060 | doi = 10.1021/acschemneuro.6b00137 }}

In the United States, 5F-MDMB-PICA was temporarily emergency scheduled by the DEA in 2019.{{cite web | title = Schedules of Controlled Substances: Temporary Placement of 5F-EDMB-PINACA, 5F-MDMB-PICA, FUB-AKB48, 5F-CUMYL-PINACA, and FUB-144 into Schedule I | url = https://www.federalregister.gov/documents/2019/04/16/2019-07460/schedules-of-controlled-substances-temporary-placement-of-5f-edmb-pinaca-5f-mdmb-pica-fub-akb48 | publisher = Federal Register | date = 2019-04-16 }} In December 2019, the UNODC announced scheduling recommendations placing 5F-MDMB-PICA into Schedule II.{{cite web|url=https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3|title=December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling}} In the United States 5F-MDMB-PICA was made a permanent Schedule I Controlled Substance nationwide on April 7, 2022.{{cite journal |title=Schedules of Controlled Substances: Placement of 5F-EDMB-PINACA, 5FMDMB-PICA, FUB-AKB48, 5F-CUMYLPINACA, and FUB-144 in Schedule I |journal=Federal Register |date=2022-04-07 |volume=87 |issue=67 |url=https://www.govinfo.gov/content/pkg/FR-2022-04-07/pdf/2022-07320.pdf}}