5F-MDMB-PICA
Chemical compound
- 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
- Methyl (2S)-2-[[1-(5-fluoropentyl)indole-3-carbonyl]amino]-3,3-dimethylbutanoate
- 1971007-88-1
- 129597835
- 68003951
- NG3U6O970A
- C22803
- Interactive image
- 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
- ^ 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
- 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.
- v
- t
- e
(comparison)
Cannabibutols |
|
---|---|
Cannabichromenes | |
Cannabicyclols |
|
Cannabidiols | |
Cannabielsoins |
|
Cannabigerols | |
Cannabiphorols |
|
Cannabinols | |
Cannabitriols |
|
Cannabivarins |
|
Delta-8-tetrahydrocannabinols |
|
Delta-9-tetrahydrocannabinols | |
Delta-10-Tetrahydrocannabinols | |
Miscellaneous cannabinoids |
|
Active metabolites |
- Arachidonoyl ethanolamide (AEA; anandamide)
- 2-Arachidonoylglycerol (2-AG)
- 2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
- 2-Oleoylglycerol (2-OG)
- N-Arachidonoyl dopamine (NADA)
- N-Arachidonylglycine (NAGly)
- 2-Arachidonoyl lysophosphatidylinositol (2-ALPI)
- N-Arachidonoyl serotonin (AA-5-HT)
- Docosatetraenoylethanolamide (DEA)
- Lysophosphatidylinositol (LPI)
- Oleamide
- Oleoylethanolamide (OEA)
- Palmitoylethanolamide (PEA)
- RVD-Hpα
- Stearoylethanolamide (SEA)
- O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids (dibenzopyrans) |
|
---|---|
Non-classical cannabinoids |
|
Adamantoylindoles |
|
Benzimidazoles | |
Benzoylindoles |
|
Cyclohexylphenols | |
Eicosanoids |
|
Hydrocarbons | |
Indazole carboxamides | |
Indazole-3- carboxamides |
|
Indole-3-carboxamides |
|
Indole-3-carboxylates | |
Naphthoylindazoles | |
Naphthoylindoles |
|
Naphthoylpyrroles | |
Naphthylmethylindenes | |
Naphthylmethylindoles | |
Phenylacetylindoles | |
Pyrazolecarboxamides |
|
Pyrrolobenzoxazines | |
Quinolinyl esters | |
Tetramethylcyclo- propanoylindazoles | |
Tetramethylcyclo- propanoylindoles | |
Tetramethylcyclo- propylindoles | |
Others |
|
enhancers
(inactivation inhibitors)
- 4-Nonylphenylboronic acid
- AM-404
- Arachidonoyl serotonin
- Arvanil
- BIA 10-2474
- Biochanin A
- CAY-10401
- CAY-10429
- Genistein
- Guineesine
- IDFP
- JNJ 1661010
- JNJ-42165279
- JZL184
- JZL195
- Kaempferol
- LY-2183240
- MK-4409
- O-1624
- O-2093
- Oleoylethanolamide (OEA)
- Olvanil
- Palmitoylethanolamide (PEA)
- PF-04457845
- PF-622
- PF-750
- PF-3845
- PHOP
- URB-447
- URB-597
- URB-602
- URB-754
- VDM-11
(antagonists/inverse
agonists/antibodies)
- AM-251
- AM-281
- AM-630
- AM-1387
- AM-4113
- AM-6527
- AM-6545
- BML-190
- Brizantin (Бризантин)
- CAY-10508
- CB-25
- CB-52
- CB-86
- Dietressa (Диетресса)
- Drinabant (AVE1625)
- Hemopressin
- Ibipinabant (SLV319)
- JTE-907
- LH-21
- LY-320,135
- MDA-77
- MJ-15
- MK-9470
- NESS-0327
- NIDA-41020
- O-606
- O-1184
- O-1248
- O-1918
- O-2050
- O-2654
- Otenabant (CP-945,598)
- PF-514273
- PipISB
- PSB-SB-487
- Rimonabant (SR141716)
- Rosonabant (E-6776)
- SR-144,528
- Surinabant (SR147778)
- Taranabant (MK-0364)
- TM-38837
- VCHSR
- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics