Etonitaces

Structural formula
	Simplified structural formula
General
Non-proprietary name	Etonitaces
other names	2 - [(4-Ethoxyphenyl) methyl] - N, N -diethyl-5-nitro-1 H -benzimidazole-1-ethanamine; 1 - [(2-Diethyl-amino) ethyl] -2- ( p -ethoxybenzyl) -5-nitrobenzimidazole; 2- p -ethoxybenzyl-1- (2-diethylaminoethyl) -5-nitrobenzimidazole; English : Etonitacene;
Molecular formula	C 22 H 28 N 4 O 3
External identifiers / databases
EC number	213-009-1
ECHA InfoCard	100,011,827
PubChem	13493
ChemSpider	12908
DrugBank	DB01462
Wikidata	Q5404835
Drug information
Drug class	Opioid - analgesic
properties
Molar mass	396.49 g · mol -1
Physical state	firmly
Melting point	110–120 and 163–164.5 ° C (hydrochloride with double melting point )
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Etonitazen is a fully synthetic opioid from the group of benzimidazoles with a very strong analgesic effect. Etonitazen is a pure agonist on the μ-opioid receptor .

description

Etonitazene was first synthesized in 1957. Etonitazen is a non-prescription narcotic drug in the Federal Republic of Germany .

chemistry

Extraction and presentation

Etonitazene is produced fully synthetically. Several synthesis processes are known, of which the one developed in Basel in 1960 is listed below. An aromatic diamine is reacted with 4-ethoxybenzylnitrile to form a heterocycle ( 1 ). It is then alkylated with 2-chloroethyl- N , N -diethylamine, whereby etonitazene is formed:

Other synthetic methods are also known.

pharmacology

effect

As an opioid, etonitazene has the same profile of effects and side effects and thus essentially the same potential risk as other opioids. Etonitazen has an analgesic potency of approx. 500-5000.

Side effects

These are tiredness, sleep disturbances , drowsiness , nausea , vomiting , edema in the legs, urinary retention , constipation and pruritus . They usually go away as tolerance develops or the dose is reduced. Sleep and sexual disorders last the longest .

Use during pregnancy and breastfeeding: Etonitazene has an effect on the fetus when taken during pregnancy.

literature

THE MERCK INDEX , 15th edition, The Royal Society of Chemistry 2013, ISBN 978-1-84973-670-1 , p. 714.

Individual evidence

^ PH List, L. Hörhammer: General part. Drug groups I . Springer-Verlag, 2013, ISBN 978-3-642-47985-4 , pp. 883 ( limited preview in Google Book Search).
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b A. Hunger, J. Kebrle, A. Rossi, K. Hoffmann: Benzimidazole derivatives and related heterocycles. II. Synthesis of 1-aminoalkyl-2-benzyl-benzimidazoles Helvetica Chimica Acta 43 (1960) pp. 800-809, doi: 10.1002 / hlca.19600430323 .

↑ A. Hunger, J. Kebrle, A. Rossi, K. Hoffmann: Synthesis of Basically Substituted, Analgesic Benzimidazole Derivatives Experientia 13 (1957) pp. 400-401, doi: 10.1007 / BF02161116 .

^ Frank Carroll, Michael Coleman: Etonitacene. Improved synthesis Journal of Medicanal Chemistry (1975) 18 pp. 318-320, doi: 10.1021 / jm00237a024 .

↑ Yong Kim, Manian Rajesh Kumar, Namjin Park, Yumi Heo, Sunwoo Lee: Copper-Catalyzed, One-Pot, Three-Component Synthesis of Benzimidazoles by Condensation and C − N Bond Formation Journal of Organic Chemistry (2011) 76 p. 9577 -9583, doi: 10.1021 / jo2019416 .

[P._H._List,_L._Hörhammer-1] PH List, L. Hörhammer: General part. Drug groups I . Springer-Verlag, 2013, ISBN 978-3-642-47985-4 , pp. 883 ( limited preview in Google Book Search).

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Hunger-3] A. Hunger, J. Kebrle, A. Rossi, K. Hoffmann: Benzimidazole derivatives and related heterocycles. II. Synthesis of 1-aminoalkyl-2-benzyl-benzimidazoles Helvetica Chimica Acta 43 (1960) pp. 800-809, doi: 10.1002 / hlca.19600430323 .

[Hunger2-4] A. Hunger, J. Kebrle, A. Rossi, K. Hoffmann: Synthesis of Basically Substituted, Analgesic Benzimidazole Derivatives Experientia 13 (1957) pp. 400-401, doi: 10.1007 / BF02161116 .

[Carroll-5] Frank Carroll, Michael Coleman: Etonitacene. Improved synthesis Journal of Medicanal Chemistry (1975) 18 pp. 318-320, doi: 10.1021 / jm00237a024 .

[Kim-6] Yong Kim, Manian Rajesh Kumar, Namjin Park, Yumi Heo, Sunwoo Lee: Copper-Catalyzed, One-Pot, Three-Component Synthesis of Benzimidazoles by Condensation and C − N Bond Formation Journal of Organic Chemistry (2011) 76 p. 9577 -9583, doi: 10.1021 / jo2019416 .