Flunitazene

Flunitazene
Legal status
Legal status	US: Schedule I;
Identifiers
	IUPAC name N,N-diethyl-2-[2-[(4-fluorophenyl)methyl]-5-nitrobenzimidazol-1-yl]ethanamine;
CAS Number	2249-36-7;
PubChem CID	156588967;
UNII	LQS4YF6P6L;
Chemical and physical data
Formula	C20H23FN4O2
Molar mass	370.428 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)CCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)F;
	InChI InChI=1S/C20H23FN4O2/c1-3-23(4-2)11-12-24-19-10-9-17(25(26)27)14-18(19)22-20(24)13-15-5-7-16(21)8-6-15/h5-10,14H,3-4,11-13H2,1-2H3; Key:ZTWHIDCAGRMKTC-UHFFFAOYSA-N;

Flunitazene (Fluonitazene) is a benzimidazole derivative with opioid effects, first developed in the 1950s as part of the research that led to better-known compounds such as etonitazene. It is one of the least potent derivatives from this class to have appeared as a designer drug, with only around the same potency as morphine, but nevertheless has been sold since around 2020, and has been linked to numerous drug overdose cases.^[1]^[2]^[3]^[4]^[5]^[6]

References

^ Lamy FR, Daniulaityte R, Barratt MJ, Lokala U, Sheth A, Carlson RG (August 2021). ""Etazene, safer than heroin and fentanyl": Non-fentanyl novel synthetic opioid listings on one darknet market". Drug and Alcohol Dependence. 225: 108790. doi:10.1016/j.drugalcdep.2021.108790. PMID 34091156. S2CID 235362241.
^ "A review of the evidence on the use and harms of 2-benzyl benzimidazole ('nitazene') and piperidine benzimidazolone ('brorphine-like') opioids" (PDF). UK: Advisory Council on the Misuse of Drugs. July 2022.
^ Walton SE, Krotulski AJ, Logan BK (March 2022). "A Forward-Thinking Approach to Addressing the New Synthetic Opioid 2-Benzylbenzimidazole Nitazene Analogs by Liquid Chromatography-Tandem Quadrupole Mass Spectrometry (LC-QQQ-MS)". Journal of Analytical Toxicology. 46 (3): 221–231. doi:10.1093/jat/bkab117. PMC 8935987. PMID 34792157.
^ Montanari E, Madeo G, Pichini S, Busardò FP, Carlier J (August 2022). "Acute Intoxications and Fatalities Associated With Benzimidazole Opioid (Nitazene Analog) Use: A Systematic Review". Therapeutic Drug Monitoring. 44 (4): 494–510. doi:10.1097/FTD.0000000000000970. PMID 35149665. S2CID 246776288.
^ Schüller M, Lucic I, Leere Øiestad ÅM, Pedersen-Bjergaard S, Øiestad EL (September 2023). "High-throughput quantification of emerging nitazene benzimidazole opioid analogs by microextraction and UHPLC-MS/MS". Journal of Analytical Toxicology. 47 (9): 787–796. doi:10.1093/jat/bkad071. PMC 10714918. PMID 37700512.
^ Balcaen M, Ventura M, Gil C, Luf A, Martins D, Cunha M, et al. (March 2023). "Challenges in Drug Surveillance: Strengthening the Analysis of New Psychoactive Substances by Harmonizing Drug Checking Services in Proficiency Testing". International Journal of Environmental Research and Public Health. 20 (5): 4628. doi:10.3390/ijerph20054628. PMC 10002093. PMID 36901637.

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[1] Lamy FR, Daniulaityte R, Barratt MJ, Lokala U, Sheth A, Carlson RG (August 2021). ""Etazene, safer than heroin and fentanyl": Non-fentanyl novel synthetic opioid listings on one darknet market". Drug and Alcohol Dependence. 225: 108790. doi:10.1016/j.drugalcdep.2021.108790. PMID 34091156. S2CID 235362241.

[2] "A review of the evidence on the use and harms of 2-benzyl benzimidazole ('nitazene') and piperidine benzimidazolone ('brorphine-like') opioids" (PDF). UK: Advisory Council on the Misuse of Drugs. July 2022.

[3] Walton SE, Krotulski AJ, Logan BK (March 2022). "A Forward-Thinking Approach to Addressing the New Synthetic Opioid 2-Benzylbenzimidazole Nitazene Analogs by Liquid Chromatography-Tandem Quadrupole Mass Spectrometry (LC-QQQ-MS)". Journal of Analytical Toxicology. 46 (3): 221–231. doi:10.1093/jat/bkab117. PMC 8935987. PMID 34792157.

[4] Montanari E, Madeo G, Pichini S, Busardò FP, Carlier J (August 2022). "Acute Intoxications and Fatalities Associated With Benzimidazole Opioid (Nitazene Analog) Use: A Systematic Review". Therapeutic Drug Monitoring. 44 (4): 494–510. doi:10.1097/FTD.0000000000000970. PMID 35149665. S2CID 246776288.

[5] Schüller M, Lucic I, Leere Øiestad ÅM, Pedersen-Bjergaard S, Øiestad EL (September 2023). "High-throughput quantification of emerging nitazene benzimidazole opioid analogs by microextraction and UHPLC-MS/MS". Journal of Analytical Toxicology. 47 (9): 787–796. doi:10.1093/jat/bkad071. PMC 10714918. PMID 37700512.

[6] Balcaen M, Ventura M, Gil C, Luf A, Martins D, Cunha M, et al. (March 2023). "Challenges in Drug Surveillance: Strengthening the Analysis of New Psychoactive Substances by Harmonizing Drug Checking Services in Proficiency Testing". International Journal of Environmental Research and Public Health. 20 (5): 4628. doi:10.3390/ijerph20054628. PMC 10002093. PMID 36901637.

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Legal status

Legal status	US: Schedule I
Identifiers
IUPAC name N,N-diethyl-2-[2-[(4-fluorophenyl)methyl]-5-nitrobenzimidazol-1-yl]ethanamine
CAS Number	2249-36-7
PubChem CID	156588967
UNII	LQS4YF6P6L
Chemical and physical data
Formula	C₂₀H₂₃FN₄O₂
Molar mass	370.428 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN(CC)CCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)F
InChI InChI=1S/C20H23FN4O2/c1-3-23(4-2)11-12-24-19-10-9-17(25(26)27)14-18(19)22-20(24)13-15-5-7-16(21)8-6-15/h5-10,14H,3-4,11-13H2,1-2H3 Key:ZTWHIDCAGRMKTC-UHFFFAOYSA-N

Flunitazene

See also

References