Protonitazepyne

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{drugbox

| drug_name = Protonitazepyne

| image = Protonitazepyne_structure.png

| legal_UK =

| legal_DE =

| C = 23 | H = 28 | N = 4 | O = 3

| IUPAC_name = 5-nitro-2-(4-propoxybenzyl)-1-(2-(pyrrolidin-1-yl)ethyl)-1H-benzo[d]imidazole

| CAS_number = 3038401-95-2

| ChemSpiderID = 115005635

| PubChem = 168322728

| UNII = T3LB6K85C7

| smiles = CCCOC1=CC=C(C=C1)CC2=NC3=C(N2CCN4CCCC4)C=CC(=C3)[N+](=O)[O-]

| StdInChI= 1S/C23H28N4O3/c1-2-15-30-20-8-5-18(6-9-20)16-23-24-21-17-19(27(28)29)7-10-22(21)26(23)14-13-25-11-3-4-12-25/h5-10,17H,2-4,11-16H2,1H3

| StdInChIKey = KCRWXNIIXGBPID-UHFFFAOYSA-N

}}

Protonitazepyne (N-pyrrolidino protonitazene) is a benzimidazole derivative with opioid effects, which has been sold as a designer drug over the internet, first being mentioned in mid 2022 and definitively identified in drug seizures in Canada in early 2023 and Ireland in late 2023.{{cite journal | vauthors = Killoran S, McNamara S, Kavanagh P, O'Brien J, Lakes R | title = Identification of N-pyrrolidino protonitazene in powders sold as heroin and associated with overdose clusters in Dublin and Cork, Ireland | journal = Drug Testing and Analysis | volume = | issue = | pages = | date = May 2024 | pmid = 38769669 | doi = 10.1002/dta.3707 }} It is an analogue of etonitazene where the ethoxy group has been extended to propoxy, and the N,N-diethyl substitution has been cyclised into a pyrrolidine ring. While formal studies into its pharmacology have yet to be carried out, it is believed to be slightly less potent than the ethoxy analogue etonitazepyne but still a potent opioid.{{cite web | title = Early signal alert: Emergence of online mentions of Protonitazepyne | url = https://ndews.org/?wysija-page=1&controller=email&action=view&email_id=374&wysijap=subscriptions | work = National Drug Early Warning System | issue = 95 | date = 29 July 2022 }}{{cite web | title = Analyzed Drug Report | url = https://health-infobase.canada.ca/src/data/DAS/pdf/en/DAS_2023Q2_en_CA.pdf | work = Drug Analysis Service and Cannabis Laboratories | publisher = Health Canada | date = April–June 2023 }}