MDMB-4en-PINACA

MDMB-4en-PINACA (also incorrectly known as 5-CL-ADB-A) is an indazole-based synthetic cannabinoid that has been sold online as a designer drug.[1][2][3][4][5][6] In 2021, MDMB-4en-PINACA was the most common synthetic cannabinoid identified by the Drug Enforcement Administration in the United States.[7] MDMB-4en-PINACA differs from 5F-MDMB-PINACA due to replacement of 5-fluoropentyl with a pent-4-ene moiety (4-en).[8]

MDMB-4en-PINACA
Legal status
Legal status
Identifiers
  • methyl (S)-3,3-dimethyl-2-(1-(pent-4-en-1-yl)-1H-indazole-3-carboxamido)butanoate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC20H27N3O3
Molar mass357.454 g·mol−1
3D model (JSmol)
  • O=C(N[C@@H](C(C)(C)C)C(OC)=O)C1=NN(CCCC=C)C2=C1C=CC=C2
  • InChI=1S/C20H27N3O3/c1-6-7-10-13-23-15-12-9-8-11-14(15)16(22-23)18(24)21-17(19(25)26-5)20(2,3)4/h6,8-9,11-12,17H,1,7,10,13H2,2-5H3,(H,21,24)/t17-/m1/s1
  • Key:LWOCBHBFWNGPGM-QGZVFWFLSA-N

It acts as a potent agonist of the CB1 receptor with an EC50 value of 2.47 nM.[9][10][11][12]

Sweden's public health agency suggested classifying MDMB-4en-PINACA as a hazardous substance, on December 18, 2019.[13]

In the United States, the DEA has filed a notice for its intent to temporarily place MDMB-4en-PINACA into Schedule I status starting on or after May 4th, 2023 for up to 2 years, during which it's possible the DEA could file for permanent scheduling within those 2 years. If it's filed on May 4, 2023, and the DEA does not file to permanent placement the temporary Schedule I order will expire on May 4, 2025.[14]

See also

References
  1. Watanabe S, Vikingsson S, Åstrand A, Gréen H, Kronstrand R (December 2019). "Biotransformation of the New Synthetic Cannabinoid with an Alkene, MDMB-4en-PINACA, by Human Hepatocytes, Human Liver Microsomes, and Human Urine and Blood". The AAPS Journal. 22 (1): 13. doi:10.1208/s12248-019-0381-3. PMID 31848852. S2CID 209393242.
  2. "MDMB-4en-PINACA". www.caymanchem.com.
  3. Erol Ozturk Y, Yeter O (January 2021). "In Vitro Phase I Metabolism of the Recently Emerged Synthetic MDMB-4en-PINACA and Its Detection in Human Urine Samples". Journal of Analytical Toxicology. 44 (9): 976–984. doi:10.1093/jat/bkaa017. PMID 32091101.
  4. Wang, Yue; Pan, Yefei; Yang, Hongkun; Liu, Jinlei; Wurita, Amin; Hasegawa, Koutaro (2022). "Quantification of MDMB-4en-PINACA and ADB-BUTINACA in human hair by gas chromatography–tandem mass spectrometry". Forensic Toxicology. 40 (2): 340–348. doi:10.1007/s11419-022-00615-z. ISSN 1860-8973. PMID 36454410. S2CID 247501663.
  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. 96 (10): 2755–2766. doi:10.1007/s00204-022-03332-z. ISSN 1432-0738. PMC 9352624. PMID 35788413. S2CID 250281976.
  6. Giorgetti, A.; Brunetti, P.; Pelotti, S.; Auwärter, V. (August 2022). "Detection of AP‐237 and synthetic cannabinoids on an infused letter sent to a German prisoner". Drug Testing and Analysis. 14 (10): 1779–1784. doi:10.1002/dta.3351. ISSN 1942-7603. PMC 9804899. PMID 35918775. S2CID 251281159.
  7. "Emerging Threat Report" (PDF). 2021.
  8. "ANALYTICAL REPORT MDMB-PINACA N1-pentyl-4-en isomer" (PDF). www.policija.si.
  9. Krotulski AJ, Cannaert A, Stove C, Logan BK (February 2021). "The next generation of synthetic cannabinoids: Detection, activity, and potential toxicity of pent-4en and but-3en analogues including MDMB-4en-PINACA". Drug Testing and Analysis. 13 (2): 427–438. doi:10.1002/dta.2935. PMID 32997377. S2CID 222148050.
  10. Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, et al. (December 2020). "Synthesis and in Vitro Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA". ACS Chemical Neuroscience. 11 (24): 4434–4446. doi:10.1021/acschemneuro.0c00644. PMID 33253529. S2CID 227246346.
  11. Pike E, Grafinger KE, Cannaert A, Ametovski A, Luo JL, Sparkes E, et al. (July 2021). "Systematic evaluation of a panel of 30 synthetic cannabinoid receptor agonists structurally related to MMB-4en-PICA, MDMB-4en-PINACA, ADB-4en-PINACA, and MMB-4CN-BUTINACA using a combination of binding and different CB1 receptor activation assays: Part I-Synthesis, analytical characterization, and binding affinity for human CB1 receptors". Drug Testing and Analysis. 13 (7): 1383–1401. doi:10.1002/dta.3037. PMID 33787091.
  12. Grafinger KE, Cannaert A, Ametovski A, Sparkes E, Cairns E, Banister SD, et al. (July 2021). "Systematic evaluation of a panel of 30 synthetic cannabinoid receptor agonists structurally related to MMB-4en-PICA, MDMB-4en-PINACA, ADB-4en-PINACA, and MMB-4CN-BUTINACA using a combination of binding and different CB1 receptor activation assays-Part II: Structure activity relationship assessment via a β-arrestin recruitment assay". Drug Testing and Analysis. 13 (7): 1402–1411. doi:10.1002/dta.3035. PMID 33769699.
  13. "Tjugotre ämnen föreslås klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 18 December 2019.
  14. "Federal Register :: Request Access".
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