Metodesnitazene information

Metodesnitazene
Legal status
Legal status	UK: Under Psychoactive Substances Act; US: Schedule I;
Identifiers
	IUPAC name N,N-diethyl-2-[2-[(4-methoxyphenyl)methyl]benzimidazol-1-yl]ethanamine;
CAS Number	14030-77-4 ; 1071546-40-1 (HCl);
PubChem CID	26412;
CompTox Dashboard (EPA)	DTXSID80161305 ;
Chemical and physical data
Formula	C21H27N3O
Molar mass	337.467 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)CCN1C2=CC=CC=C2N=C1CC3=CC=C(C=C3)OC;
	InChI InChI=1S/C21H27N3O/c1-4-23(5-2)14-15-24-20-9-7-6-8-19(20)22-21(24)16-17-10-12-18(25-3)13-11-17/h6-13H,4-5,14-16H2,1-3H3; Key:SFNKTTXBZXVGOH-UHFFFAOYSA-N;

Metodesnitazene (also known as Metazene) is a benzimidazole derivative with opioid effects, though unlike related compounds such as metonitazene and etodesnitazene which are many times more potent, metodesnitazene is only around the same potency as morphine in animal studies.^[1]^[2]^[3]^[4]^[5] It was proposed by the DEA to be placed under legal control in the US in December 2021.^[6]

^ 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. 43 (3): 800–809. doi:10.1002/hlca.19600430323.
^ Vandeputte M, Van Uytfanghe K, Layle N, Germaine DS, Iula D, Stove C (12 November 2020). "Synthesis, chemical characterization, and µ-opioid receptor activity assessment of the emerging group of nitazene new synthetic opioids". Authorea. doi:10.22541/au.160520665.59016513/v1. S2CID 234646245.
^ 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.
^ Lamy FR, Daniulaityte R, Barratt MJ, Lokala U, Sheth A, Carlson RG (August 2021). ""Etazene, safer than heroin and fentanyl": Non-fentanyl novel synthetic opioid listings on one darknet market". Drug and Alcohol Dependence. 225: 108790. doi:10.1016/j.drugalcdep.2021.108790. PMID 34091156. S2CID 235362241.
^ Sisco E, Burns A, Moorthy A (2021). "Development and Evaluation of a Synthetic Opioid Targeted Gas Chromatography Mass Spectrometry (GC-MS) Method". Journal of Forensic Sciences. 66 (6): 2369–2380. doi:10.33774/chemrxiv-2021-0pcnq. PMC 9922096. PMID 34459514. S2CID 240520700.
^ "Schedules of Controlled Substances: Temporary Placement of Butonitazene, Etodesnitazene, Flunitazene, Metodesnitazene, Metonitazene, N-pyrrolidino etonitazene, and Protonitazene in Schedule I." A Proposed Rule by the Drug Enforcement Administration. 7 December 2021.

[1] 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. 43 (3): 800–809. doi:10.1002/hlca.19600430323.

[2] Vandeputte M, Van Uytfanghe K, Layle N, Germaine DS, Iula D, Stove C (12 November 2020). "Synthesis, chemical characterization, and µ-opioid receptor activity assessment of the emerging group of nitazene new synthetic opioids". Authorea. doi:10.22541/au.160520665.59016513/v1. S2CID 234646245.

[pmid33760580-3] 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.

[pmid34091156-4] Lamy FR, Daniulaityte R, Barratt MJ, Lokala U, Sheth A, Carlson RG (August 2021). ""Etazene, safer than heroin and fentanyl": Non-fentanyl novel synthetic opioid listings on one darknet market". Drug and Alcohol Dependence. 225: 108790. doi:10.1016/j.drugalcdep.2021.108790. PMID 34091156. S2CID 235362241.

[5] Sisco E, Burns A, Moorthy A (2021). "Development and Evaluation of a Synthetic Opioid Targeted Gas Chromatography Mass Spectrometry (GC-MS) Method". Journal of Forensic Sciences. 66 (6): 2369–2380. doi:10.33774/chemrxiv-2021-0pcnq. PMC 9922096. PMID 34459514. S2CID 240520700.

[6] "Schedules of Controlled Substances: Temporary Placement of Butonitazene, Etodesnitazene, Flunitazene, Metodesnitazene, Metonitazene, N-pyrrolidino etonitazene, and Protonitazene in Schedule I." A Proposed Rule by the Drug Enforcement Administration. 7 December 2021.

Metodesnitazene information

and 8 Related for: Metodesnitazene information

Metodesnitazene

Benzimidazole

Etodesnitazene

List of benzimidazole opioids

Protonitazene

Butonitazene

Opioid

List of designer drugs

Legal status

Legal status	UK: Under Psychoactive Substances Act US: Schedule I
Identifiers
IUPAC name N,N-diethyl-2-[2-[(4-methoxyphenyl)methyl]benzimidazol-1-yl]ethanamine
CAS Number	14030-77-4 1071546-40-1 (HCl)
PubChem CID	26412
CompTox Dashboard (EPA)	DTXSID80161305
Chemical and physical data
Formula	C₂₁H₂₇N₃O
Molar mass	337.467 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN(CC)CCN1C2=CC=CC=C2N=C1CC3=CC=C(C=C3)OC
InChI InChI=1S/C21H27N3O/c1-4-23(5-2)14-15-24-20-9-7-6-8-19(20)22-21(24)16-17-10-12-18(25-3)13-11-17/h6-13H,4-5,14-16H2,1-3H3 Key:SFNKTTXBZXVGOH-UHFFFAOYSA-N