Protonitazepyne

Protonitazepyne
Identifiers
	IUPAC name 5-nitro-2-(4-propoxybenzyl)-1-(2-(pyrrolidin-1-yl)ethyl)-1H-benzo[d]imidazole;
CAS Number	3038401-95-2;
PubChem CID	168322728;
ChemSpider	115005635;
UNII	T3LB6K85C7;
Chemical and physical data
Formula	C23H28N4O3
Molar mass	408.502 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCOC1=CC=C(C=C1)CC2=NC3=C(N2CCN4CCCC4)C=CC(=C3)[N+](=O)[O-];
	InChI InChI=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; Key: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.^[1] It has since been identified by CanTEST in May 2024 in Australia^[2]^[3] and in late 2025 in Brazil by the State University of Campinas poison control center.^[4]

It is an analogue of protonitazene where the N,N-diethyl group has been substituted for pyrrolidine group. While formal studies into its pharmacology have yet to be carried out, it is has an in vitro potency approximately 350x times that of morphine.^[5]

References

↑ Killoran S, McNamara S, Kavanagh P, O'Brien J, Lakes R (May 2024). "Identification of N-pyrrolidino protonitazene in powders sold as heroin and associated with overdose clusters in Dublin and Cork, Ireland". Drug Testing and Analysis. 17 (3): 350–357. doi:10.1002/dta.3707. PMID 38769669.
↑ Curtis B, Lawes DJ, Caldicott D, McLeod MD (October 2025). "Identification of the Novel Synthetic Opioid N-Pyrrolidino Isotonitazene at an Australian Drug Checking Service". Drug Testing and Analysis. 17 (10): 1996–2004. doi:10.1002/dta.3910. PMC 12489282. PMID 40384477.
↑ "N-pyrrolidino protonitazene found in brown powder sample". The Know. Australia: National Clinical Centre for Research of Emerging Drugs (NCCRED). 2024-05-18. Retrieved 2025-08-26.
↑ "Unicamp identifica nova droga 50 vezes mais potente que fentanil pela 1ª vez no Brasil; entenda". G1 (in Brazilian Portuguese). 2025-10-12. Retrieved 2025-10-12.
↑ De Vrieze LM, Walton SE, Pottie E, Papsun D, Logan BK, Krotulski AJ, et al. (September 2024). "In vitro structure-activity relationships and forensic case series of emerging 2-benzylbenzimidazole 'nitazene' opioids". Archives of Toxicology. 98 (9): 2999–3018. Bibcode:2024ArTox..98.2999D. doi:10.1007/s00204-024-03774-7. PMC 11324687. PMID 38877156.

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[Killoran_2024-1] Killoran S, McNamara S, Kavanagh P, O'Brien J, Lakes R (May 2024). "Identification of N-pyrrolidino protonitazene in powders sold as heroin and associated with overdose clusters in Dublin and Cork, Ireland". Drug Testing and Analysis. 17 (3): 350–357. doi:10.1002/dta.3707. PMID 38769669.

[2] Curtis B, Lawes DJ, Caldicott D, McLeod MD (October 2025). "Identification of the Novel Synthetic Opioid N-Pyrrolidino Isotonitazene at an Australian Drug Checking Service". Drug Testing and Analysis. 17 (10): 1996–2004. doi:10.1002/dta.3910. PMC 12489282. PMID 40384477.

[3] "N-pyrrolidino protonitazene found in brown powder sample". The Know. Australia: National Clinical Centre for Research of Emerging Drugs (NCCRED). 2024-05-18. Retrieved 2025-08-26.

[4] "Unicamp identifica nova droga 50 vezes mais potente que fentanil pela 1ª vez no Brasil; entenda". G1 (in Brazilian Portuguese). 2025-10-12. Retrieved 2025-10-12.

[5] De Vrieze LM, Walton SE, Pottie E, Papsun D, Logan BK, Krotulski AJ, et al. (September 2024). "In vitro structure-activity relationships and forensic case series of emerging 2-benzylbenzimidazole 'nitazene' opioids". Archives of Toxicology. 98 (9): 2999–3018. Bibcode:2024ArTox..98.2999D. doi:10.1007/s00204-024-03774-7. PMC 11324687. PMID 38877156.

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Identifiers

IUPAC name 5-nitro-2-(4-propoxybenzyl)-1-(2-(pyrrolidin-1-yl)ethyl)-1H-benzo[d]imidazole
CAS Number	3038401-95-2
PubChem CID	168322728
ChemSpider	115005635
UNII	T3LB6K85C7
Chemical and physical data
Formula	C₂₃H₂₈N₄O₃
Molar mass	408.502 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCOC1=CC=C(C=C1)CC2=NC3=C(N2CCN4CCCC4)C=CC(=C3)[N+](=O)[O-]
InChI InChI=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 Key:KCRWXNIIXGBPID-UHFFFAOYSA-N

Protonitazepyne

See also

References