Butonitazene
{{Short description|Chemical compound}}
{{infobox drug
| drug_name = Butonitazene
| image = Butonitazine.svg
| legal_AU =
| legal_BR = F1
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}
| legal_CA =
| legal_DE = Anlage II
| legal_NZ =
| legal_UK = PSA
| legal_US = Schedule I
| legal_EU =
| legal_UN =
| C = 24 | H = 32 | N = 4 | O = 3
| IUPAC_name = 2-[(4-Butoxyphenyl)methyl]-5-nitro-1-(2-pyrrolidin-1-ylethyl)benzimidazole
| CAS_number = 95810-54-1
| ChemSpiderID = 97091820
| ChEBI = 234364
| PubChem = 156588955
| UNII = C4CE9FVR7N
| smiles = CCCCOC1=CC=C(C=C1)CC2=NC3=C(N2CCN(CC)CC)C=CC(=C3)[N+](=O)[O-]
| StdInChI=1S/C24H32N4O3/c1-4-7-16-31-21-11-8-19(9-12-21)17-24-25-22-18-20(28(29)30)10-13-23(22)27(24)15-14-26(5-2)6-3/h8-13,18H,4-7,14-17H2,1-3H3
| StdInChIKey = UZZPOLCDCVWLAZ-UHFFFAOYSA-N
}}
Butonitazene is a benzimidazole derivative with opioid effects, which has been sold over the internet as a designer drug. It has relatively low potency compared to many related compounds, and has generally been encountered as a component of mixtures with other substances rather than in its pure form. However, it is still several times the potency of morphine and has been implicated in several cases of drug overdose.{{cite journal | vauthors = Schumann JL, Syrjanen R, Alford K, Mashetty S, Castle JW, Rotella J, Maplesden J, Greene SL | display-authors = 6 | title = Intoxications in an Australian Emergency Department Involving 'Nitazene' Benzylbenzimidazole Synthetic Opioids (Etodesnitazene, Butonitazene and Protonitazene) | journal = Journal of Analytical Toxicology | date = August 2022 | volume = 47 | issue = 1 | pages = e6–e9 | pmid = 35983900 | doi = 10.1093/jat/bkac062 }}{{cite journal | vauthors = Montanari E, Madeo G, Pichini S, Busardò FP, Carlier J | title = Acute Intoxications and Fatalities Associated With Benzimidazole Opioid (Nitazene Analog) Use: A Systematic Review | journal = Therapeutic Drug Monitoring | volume = 44 | issue = 4 | pages = 494–510 | date = August 2022 | pmid = 35149665 | doi = 10.1097/FTD.0000000000000970 | s2cid = 246776288 }}{{cite journal | vauthors = Walton SE, Krotulski AJ, Logan BK | title = 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 = Journal of Analytical Toxicology | volume = 46 | issue = 3 | pages = 221–231 | date = March 2022 | pmid = 34792157 | doi = 10.1093/jat/bkab117 | pmc = 8935987 }} Butonitazene is a Schedule I drug in the US, along with several related compounds.{{cite journal | url = https://www.govinfo.gov/content/pkg/FR-2022-04-12/pdf/2022-07640.pdf | publisher = Drug Enforcement Administration | title = 21 CFR Part 1308. [Docket No. DEA–900] Schedules of Controlled Substances: Temporary Placement of Butonitazene, Etodesnitazene, Flunitazene, Metodesnitazene, Metonitazene, N-Pyrrolidino etonitazene, and Protonitazene in Schedule I. | journal = Federal Register | date = 12 April 2022 | volume = 87 | issue = 70 | page = 21556 }}