Isotonitazepyne

Isotonitazepyne
Identifiers
IUPAC name
  • 5-nitro-2-[4-(2-propoxy)benzyl]-1-[2-(pyrrolidin-1-yl)ethyl]-1H-benzo[d]imidazole
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC23H28N4O3
Molar mass408.502 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)OC1=CC=C(C=C1)CC2=NC3=C(N2CCN4CCCC4)C=CC(=C3)[N+](=O)[O-]
InChI
  • InChI=1S/C23H28N4O3/c1-17(2)30-20-8-5-18(6-9-20)15-23-24-21-16-19(27(28)29)7-10-22(21)26(23)14-13-25-11-3-4-12-25/h5-10,16-17H,3-4,11-15H2,1-2H3
  • Key:VRKDSDBBRNHHCR-UHFFFAOYSA-N

Isotonitazepyne (N-pyrrolidino-isotonitazene, NPI) is a benzimidazole derivative with potent opioid effects, which has been sold as a designer drug over the internet. Its in vitro potency is approximately 1000 times that of morphine.[1] One sample of counterfeit oxycodone pills were found to contain between 3.3 and 3.5 mg of NPI per pill and no oxycodone.[2]

Timeline of detections

NPI was first identified in the UK in August 2024 by WEDINOS as samples W054816 and W057074,[3][4] then the full chemical characterisation and first literature reported sample was provided by CanTEST in Australia in September 2024,[5][2]. NPI was later detected in the Netherlands in May 2025,[6] and in Finland in early 2025.[7].

This section is not exhaustive and does not include information for all countries with laws covering isotonitazepyne.

USA

Virginia

It is specifically listed as an illegal drug in the US state of Virginia.[8]

United Kingdom

Since 15 January 2025 it is covered by the UK's generic definition on 2-benzyl benzimidazole derived opioids[9][10] because it contains the backbone with only the following modifications:[11]

  • The nitrogen of the ethanamine (and no other atoms of the side chain) is included in a cyclic structure.
  • The phenyl ring of the benzyl system is substituted by an alkoxy group containing three carbon atoms.
  • The 5- position of the benzimidazole system is substituted by a nitro group.

See also

References

  1. ↑ 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.
  2. 1 2 Lawes DJ, Caldicott D, McLeod MD, Curtis B (2025). "Identification of the Novel Synthetic Opioid N-Pyrrolidino Isotonitazene at an Australian Drug Checking Service". Drug Testing and Analysis. n/a (n/a) dta.3910. doi:10.1002/dta.3910. ISSN 1942-7611. PMC 12489282. PMID 40384477.
  3. ↑ WEDINOS (2024-09-01). WEDINOS PHILTRE August 2024 Detection report (PDF). WEDINOS. p. 7.
  4. ↑ "WEDINOS: Test Outcome for W057074". 2024-08-07.
  5. ↑ "N-pyrrolidino isotonitazene found in counterfeit oxycodone pill r". CanTEST. 9 September 2024. Archived from the original on 9 September 2024. Retrieved 9 September 2024 – via Instagram.
  6. ↑ kevino (2025-03-18). "Waarschuwing: Namaak-oxycodonpillen met het levensgevaarlijke isotonitazepyne in omloop". Trimbos-instituut (in Dutch). Retrieved 2025-05-30.
  7. ↑ Kriikku P, Pelander A, Jylhä A, Ojanperä I. Post-Mortem Identification and Toxicological Findings of Fluetonitazepyne and Isotonitazepyne. Drug Testing and Analysis 2025 doi:10.1002/dta.3928
  8. ↑ "18VAC110-20-322. Placement of chemicals in Schedule I." Code of Virginia. 2023.
  9. ↑ "The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2024 and The Misuse of Drugs and Misuse of Drugs (Designation) (England and Wales and Scotland) (Amendment) (No. 2) Regulations 2024". GOV.UK. Retrieved 2025-05-30.
  10. ↑ "Britain working at pace to curb rising synthetic drugs threat". GOV.UK. Retrieved 2025-06-12.
  11. ↑ "Nitazenes detected in fake oxycodone tablets in Europe and the UK – Reagent Tests UK". www.reagent-tests.uk. Retrieved 2025-06-20.


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