Protonitazene

Protonitazene
Legal status
Legal status	BR: Class F1 (Prohibited narcotics); DE: Anlage II (Authorized trade only, not prescriptible); UK: Under Psychoactive Substances Act; US: Schedule I;
Identifiers
	IUPAC name N,N-diethyl-2-[5-nitro-2-[(4-propoxyphenyl)methyl]benzimidazol-1-yl]ethanamine;
CAS Number	95958-84-2;
PubChem CID	156589001;
UNII	4A6RZQ7M2V;
KEGG	C22683;
CompTox Dashboard (EPA)	DTXSID301342658 ;
Chemical and physical data
Formula	C23H30N4O3
Molar mass	410.518 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCOC1=CC=C(C=C1)CC2=NC3=C(N2CCN(CC)CC)C=CC(=C3)[N+](=O)[O-];
	InChI InChI=1S/C23H30N4O3/c1-4-15-30-20-10-7-18(8-11-20)16-23-24-21-17-19(27(28)29)9-12-22(21)26(23)14-13-25(5-2)6-3/h7-12,17H,4-6,13-16H2,1-3H3; Key:SJHUJFHOXYDSJY-UHFFFAOYSA-N;

Protonitazene is a benzimidazole derivative with potent opioid effects which has been sold over the internet as a designer drug since 2019, and has been identified in various European countries, as well as Canada, the US and Australia.^[1] It has been linked to numerous cases of drug overdose, and is a Schedule I drug in the US.^[2]^[3]^[4]^[5]^[6]

It was developed by a Swiss pharmaceutical company in the 1950s as an alternative to morphine, but was never adopted due to severe side effects.^[7]

References

^ Edinoff AN, Martinez Garza D, Vining SP, Vasterling ME, Jackson ED, Murnane KS, Kaye AM, Fair RN, Torres YJ, Badr AE, Cornett EM, Kaye AD (April 2023). "New Synthetic Opioids: Clinical Considerations and Dangers". Pain and Therapy. 12 (2): 399–421. doi:10.1007/s40122-023-00481-6. PMC 9950705. PMID 36826742.
^ Schumann JL, Syrjanen R, Alford K, Mashetty S, Castle JW, Rotella J, et al. (August 2022). "Intoxications in an Australian Emergency Department Involving 'Nitazene' Benzylbenzimidazole Synthetic Opioids (Etodesnitazene, Butonitazene and Protonitazene)". Journal of Analytical Toxicology. 47 (1): e6 – e9. doi:10.1093/jat/bkac062. PMID 35983900.
^ Kanamori T, Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Iwata YT (November 2022). "Analysis of highly potent synthetic opioid nitazene analogs and their positional isomers". Drug Testing and Analysis. 15 (4): 449–457. doi:10.1002/dta.3415. PMID 36437623. S2CID 254042990.
^ Papsun DM, Krotulski AJ, Logan BK (December 2022). "Proliferation of Novel Synthetic Opioids in Postmortem Investigations After Core-Structure Scheduling for Fentanyl-Related Substances". The American Journal of Forensic Medicine and Pathology. 43 (4): 315–327. doi:10.1097/PAF.0000000000000787. PMID 36103391. S2CID 252220135.
^ Walton SE, Krotulski AJ, Logan BK (March 2022). "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 of Analytical Toxicology. 46 (3): 221–231. doi:10.1093/jat/bkab117. PMC 8935987. PMID 34792157.
^ "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." (PDF). Federal Register. 87 (70). Drug Enforcement Administration: 21556. 12 April 2022.
^ Faugstad, Sebastian (23 November 2022). "20-åring døde etter inntak av nytt, livsfarlig rusmiddel" [20-year-old died after consuming a new, life-threatening drug]. NRK (in Norwegian Bokmål). Retrieved 26 July 2023. Protonitazen er et syntetisk opioid som ble utviklet av et sveitsisk legemiddelselskap på 50-tallet. Det var ment som et alternativ til morfin, men på grunn av alvorlige bivirkninger ble stoffet aldri tatt i bruk. [Protonitazen is a synthetic opioid that was developed by a Swiss pharmaceutical company in the 50s. It was intended as an alternative to morphine, but due to severe side effects, the drug was never used.]

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[pmid36826742-1] Edinoff AN, Martinez Garza D, Vining SP, Vasterling ME, Jackson ED, Murnane KS, Kaye AM, Fair RN, Torres YJ, Badr AE, Cornett EM, Kaye AD (April 2023). "New Synthetic Opioids: Clinical Considerations and Dangers". Pain and Therapy. 12 (2): 399–421. doi:10.1007/s40122-023-00481-6. PMC 9950705. PMID 36826742.

[2] Schumann JL, Syrjanen R, Alford K, Mashetty S, Castle JW, Rotella J, et al. (August 2022). "Intoxications in an Australian Emergency Department Involving 'Nitazene' Benzylbenzimidazole Synthetic Opioids (Etodesnitazene, Butonitazene and Protonitazene)". Journal of Analytical Toxicology. 47 (1): e6 – e9. doi:10.1093/jat/bkac062. PMID 35983900.

[3] Kanamori T, Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Iwata YT (November 2022). "Analysis of highly potent synthetic opioid nitazene analogs and their positional isomers". Drug Testing and Analysis. 15 (4): 449–457. doi:10.1002/dta.3415. PMID 36437623. S2CID 254042990.

[4] Papsun DM, Krotulski AJ, Logan BK (December 2022). "Proliferation of Novel Synthetic Opioids in Postmortem Investigations After Core-Structure Scheduling for Fentanyl-Related Substances". The American Journal of Forensic Medicine and Pathology. 43 (4): 315–327. doi:10.1097/PAF.0000000000000787. PMID 36103391. S2CID 252220135.

[5] Walton SE, Krotulski AJ, Logan BK (March 2022). "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 of Analytical Toxicology. 46 (3): 221–231. doi:10.1093/jat/bkab117. PMC 8935987. PMID 34792157.

[6] "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." (PDF). Federal Register. 87 (70). Drug Enforcement Administration: 21556. 12 April 2022.

[7] Faugstad, Sebastian (23 November 2022). "20-åring døde etter inntak av nytt, livsfarlig rusmiddel" [20-year-old died after consuming a new, life-threatening drug]. NRK (in Norwegian Bokmål). Retrieved 26 July 2023. Protonitazen er et syntetisk opioid som ble utviklet av et sveitsisk legemiddelselskap på 50-tallet. Det var ment som et alternativ til morfin, men på grunn av alvorlige bivirkninger ble stoffet aldri tatt i bruk. [Protonitazen is a synthetic opioid that was developed by a Swiss pharmaceutical company in the 50s. It was intended as an alternative to morphine, but due to severe side effects, the drug was never used.]

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See also

References