FRDD

Forensically-Relevant Drug Database

NPS Discover

Description

Preferred Drug Name

N-Pyrrolidino Protonitazene

Brief Description

The following information was compiled in June 2023 and is subject to change as new research is conducted and as new information becomes available: Description: N-Pyrrolidino protonitazene is a novel synthetic opioid bearing structural resemblance to protonitazene, N-pyrrolidino etonitazene, and other nitazene (2-benzylbenzimidazole) analogues and is an isomer of N-pyrrolidino isotonitazene. In January 2023, N-pyrrolidino protonitazene was detected for the first time in the United States. Our laboratory continues to gather toxicology data for this novel drug. Sample Source: NMS Labs – Toxicology Laboratory, NMS Labs – Criminalistics Laboratory, etc. Sample Appearance: Drug Material – Brown Powder. Toxicology – Blood Specimens. Pharmacology: Limited information regarding the pharmacology of N-pyrrolidino protonitazene is currently known. Recent in vitro studies examining activity and potency found that N-pyrrolidino protonitazene is an active opioid with potency approximately 25 times greater than that of fentanyl [unpublished data from L. De Vrieze and C. Stove]. Based on structural similarity, N-pyrrolidino protonitazene is expected to exhibit similar adverse effects to other nitazene analogues. Toxicology: N-Pyrrolidino protonitazene has been detected in eight toxicology cases at the CFSRE. Drug Materials: N-Pyrrolidino protonitazene has been identified in one drug material at the CFSRE. Demographics / Geographics: Cases originated from at least three states, including Illinois, West Virginia, and Minnesota. In death investigations, decedents were predominantly male, ranging in age from 20s-70s. Legal Status: N-Pyrrolidino protonitazene is not explicitly scheduled in the United States.

Structure


Nomenclature

Formal Name (IUPAC)

5-nitro-2-[(4-propoxyphenyl)methyl]-1-(2-pyrrolidin-1-ylethyl)benzimidazole

Synonyms

Protonitazepyne

Identifiers

CAS Numbers

3038401-95-2

Chemistry

Chemical Formula

C23H28N4O3

Molecular Mass

408.49

Molecular Ion

408

Exact Mass

409.2234

SMILES

CCCOC(C=C1)=CC=C1CC2=NC3=CC([N+]([O-])=O)=CC=C3N2CCN4CCCC4

InChI String

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

InChI Key

KCRWXNIIXGBPID-UHFFFAOYSA-N

GCMS Analytics

Lab

CFSRE (Willow Grove, PA)

Comments

Sample Preparation: 

Sample: Acid / base extraction

Standard (above): Diluted in methanol

Instrument:Agilent 5975 Series GC/MSD
Methods:http://www.cfsre.org/nps-discovery/monographs

 

Images

Fragments

84
107
42

HRMS Analytics

Lab

CFSRE (Willow Grove, PA)

Comments

Sample Preparation:Acid / base extraction
Instrument: Sciex TripleTOF® 5600+ LC-QTOF-MS
Methods:https://www.cfsre.org/nps-discovery/monographs

 

Images

Fragments

98.0956
409.223

Drug Origins and Uses

Drug Origins and Uses

Illicit, Synthetic

Biological Effects

Biological Effects

Analgesic, Depressant

Target Receptor or Neurotransmitter

Target Receptor or Neurotransmitter

MOR

Pharmacodynamics

Pharmacodynamics

Agonist

Toxicology Postmortem Fatal

Source

The American Journal of Forensic Medicine and Pathology

Title

New and Emerging “Nitazene” Analogues Appearing in Medicolegal Death Investigations N-Pyrrolidino Protonitazene and N-Desethyl Isotonitazene

Reference Link


Toxicology Data Clinical Nonfatal

Source

Drug Testing and Analysis

Title

Identification of N-pyrrolidino protonitazene in powders sold as heroin and associated with overdose clusters in Dublin and Cork, Ireland

Reference Link


Drug Control

US Controlled Substance Schedule

Schedule I


Analytical Literature

Source

National Forensic Laboratory

Title

N-Pyrrolidino Protonitazene (C23H28N4O3)

Reference Link


Published January 23, 2026