ETAZEN

Desnitroetonitazene
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 2-[2-[(4-Ethoxyphenyl)methyl]benzimidazol-1-yl]-N,N-diethylethanamine;
CAS Number	14030-76-3 ;
PubChem CID	149797386;
UNII	H7YW5L26CS;
KEGG	C22827;
CompTox Dashboard ( EPA)	DTXSID601336496 ;
Chemical and physical data
Formula	C22H29N3O
Molar mass	351.494 g·mol−1
3D model ( JSmol)	Interactive image;
	SMILES CCN(CC)CCN1C2=CC=CC=C2N=C1CC3=CC=C(C=C3)OCC;
	InChI InChI=1S/C22H29N3O/c1-4-24(5-2)15-16-25-21-10-8-7-9-20(21)23-22(25)17-18-11-13-19(14-12-18)26-6-3/h7-14H,4-6,15-17H2,1-3H3; Key:BMLPNUNXHUGDOI-UHFFFAOYSA-N;

Etodesnitazene (Desnitroetonitazene, Etazen, Etazene, Etazone) is a benzimidazole derived opioid analgesic drug, which was originally developed in the late 1950s alongside etonitazene and a range of related derivatives.^[1] It is many times less potent than etonitazene itself, but still 70x more potent than morphine in animal studies. Corresponding analogues where the N,N-diethyl group is replaced by piperidine or pyrrolidine rings also retain significant activity (10x and 20x morphine respectively).^[2] Etodesnitazene has been sold as a designer drug,^[3] first being identified in both Poland and Finland in March 2020.^[4]^[5]

References

^ Ujváry I, Christie R, Evans-Brown M, Gallegos A, Jorge R, de Morais J, Sedefov R (April 2021). "DARK Classics in Chemical Neuroscience: Etonitazene and Related Benzimidazoles". ACS Chemical Neuroscience. 12 (7): 1072–1092. doi: 10.1021/acschemneuro.1c00037. PMID 33760580. S2CID 232356192.
^ Hunger A, Kebrle J, Rossi A, Hoffmann K (1960). "Benzimidazol-Derivate und verwandte Heterocyclen. II. Synthese von 1-Aminoalkyl-2-benzyl-benzimidazolen". Helvetica Chimica Acta (in German). 43 (3): 800–809. doi: 10.1002/hlca.19600430323.
^ Siczek M, Zawadzki M, Siczek M, Chłopaś-Konowałek A, Szpot P (2020). "Etazene (N,N-diethyl-2-{[(4-ethoxyphenyl)methyl]-1H-benzimidazol-1-yl}-ethan-1-amine (dihydrochloride)): a novel benzimidazole opioid NPS identified in seized material: crystal structure and spectroscopic characterization". Forensic Toxicology. doi: 10.1007/s11419-020-00552-9. ISSN 1860-8973.
^ Siczek M, Zawadzki M, Siczek M, Chłopaś-Konowałek A, Szpot P (January 2021). "Etazene (N,N-diethyl-2-{[(4-ethoxyphenyl)methyl]-1H-benzimidazol-1-yl}-ethan-1-amine (dihydrochloride)): a novel benzimidazole opioid NPS identified in seized material: crystal structure and spectroscopic characterization". Forensic Toxicology. 39 (1): 146–155. doi: 10.1007/s11419-020-00552-9. ISSN 1860-8965.
^ "EU Early Warning System Situation Report. Situation report 1" (PDF). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). June 2020.

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[1] Ujváry I, Christie R, Evans-Brown M, Gallegos A, Jorge R, de Morais J, Sedefov R (April 2021). "DARK Classics in Chemical Neuroscience: Etonitazene and Related Benzimidazoles". ACS Chemical Neuroscience. 12 (7): 1072–1092. doi: 10.1021/acschemneuro.1c00037. PMID 33760580. S2CID 232356192.

[2] Hunger A, Kebrle J, Rossi A, Hoffmann K (1960). "Benzimidazol-Derivate und verwandte Heterocyclen. II. Synthese von 1-Aminoalkyl-2-benzyl-benzimidazolen". Helvetica Chimica Acta (in German). 43 (3): 800–809. doi: 10.1002/hlca.19600430323.

[3] Siczek M, Zawadzki M, Siczek M, Chłopaś-Konowałek A, Szpot P (2020). "Etazene (N,N-diethyl-2-{[(4-ethoxyphenyl)methyl]-1H-benzimidazol-1-yl}-ethan-1-amine (dihydrochloride)): a novel benzimidazole opioid NPS identified in seized material: crystal structure and spectroscopic characterization". Forensic Toxicology. doi: 10.1007/s11419-020-00552-9. ISSN 1860-8973.

[4] Siczek M, Zawadzki M, Siczek M, Chłopaś-Konowałek A, Szpot P (January 2021). "Etazene (N,N-diethyl-2-{[(4-ethoxyphenyl)methyl]-1H-benzimidazol-1-yl}-ethan-1-amine (dihydrochloride)): a novel benzimidazole opioid NPS identified in seized material: crystal structure and spectroscopic characterization". Forensic Toxicology. 39 (1): 146–155. doi: 10.1007/s11419-020-00552-9. ISSN 1860-8965.

[5] "EU Early Warning System Situation Report. Situation report 1" (PDF). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). June 2020.

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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 2-[2-[(4-Ethoxyphenyl)methyl]benzimidazol-1-yl]-N,N-diethylethanamine
CAS Number	14030-76-3^Y
PubChem CID	149797386
UNII	H7YW5L26CS
KEGG	C22827
CompTox Dashboard ( EPA)	DTXSID601336496
Chemical and physical data
Formula	C₂₂H₂₉N₃O
Molar mass	351.494 g·mol⁻¹
3D model ( JSmol)	Interactive image
SMILES CCN(CC)CCN1C2=CC=CC=C2N=C1CC3=CC=C(C=C3)OCC
InChI InChI=1S/C22H29N3O/c1-4-24(5-2)15-16-25-21-10-8-7-9-20(21)23-22(25)17-18-11-13-19(14-12-18)26-6-3/h7-14H,4-6,15-17H2,1-3H3 Key:BMLPNUNXHUGDOI-UHFFFAOYSA-N