Benzimidazole opioids are a class of synthetic opioids that contain a benzimidazole core structure. The pain-relieving properties of these substances were discovered in the mid-1950s by the Swiss company Ciba AG. The most important subgroup are the nitazene opioids, which since 2019 have become increasingly widespread as narcotics in North America and Europe, as well as West Africa. Some other benzimidazole-containing opioids are classified separately under the orphine subgroup. There is currently no medical usage due to the high potencies of certain analogs.[1]
History
Desnitazene
In 1957, the pharmaceutical research department of Ciba AG published the discovery of the (low) analgesic effect of 1-(β-diethylaminoethyl)-2-benzylbenzimidazole (desnitazene).[2] Shortly afterwards, the nitazenes were discovered in structure-activity relationship studies.[3][4]
Structure-activity relationship
The class of nitazene opioids is defined chemically by the presence of the benzimidazole core structure and pharmacologically by mu opioid agonist activity. The compounds are derived from the historical prototype 1-(β-diethylaminoethyl)-2-benzylbenzimidazole (desnitazene). The replacement of the N,N-dialkylamino unit by pyrrolidinyl or piperidinyl, which is found in nitazepyne and nitazepipne compounds, falls into the spectrum of designer drugs. Substitution of the benzyl for thienylmethyl, pyridylmethyl, α-napthylmethyl or styryl has a potency-reducing effect.[5][6] Substitution in position 4 of the benzyl affects analgesic potency in the following order: ethoxy > isopropyloxy > n-propyloxy > methoxy > methylthio > H/Cl/F > hydroxy. The most potent of the known compounds contain a nitro group in position 5.[6] The replacement of benzimidazole with an indole has been known from studies conducted by Ciba AG since 1963.
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5-Bromo-2-chlorobenzimidazole
Product Information Product Name 5-Bromo-2-chlorobenzimidazole Brand Name ChemScene Product Number CS-WAA0077 CAS 683240-76-8 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 11615568 IUPAC Name 6-bromo-2-chloro-1H-benzimidazole InChI…
Product Information Product Name 1-Methyl-1H-benzimidazole-6-carboxaldehyde Brand Name ChemScene Product Number CS-0209822 CAS 181867-19-6 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 22464914 IUPAC Name 3-methylbenzimidazole-5-carbaldehyde InChI…
Product Information Product Name 2-Chloro-7-(trifluoromethyl)-1H-benzimidazole Brand Name ChemScene Product Number CS-0654558 CAS 1075753-27-3 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 74892049 IUPAC Name 2-chloro-4-(trifluoromethyl)-1H-benzimidazole InChI…
Product Information Product Name 2-Chlorobenzimidazole Brand Name ChemScene Product Number CS-W016291 CAS 4857-06-1 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 78572 IUPAC Name 2-chloro-1H-benzimidazole InChI…
Product Information Product Name 2-Acetylbenzimidazole Brand Name ChemScene Product Number CS-W023047 CAS 939-70-8 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 70322 IUPAC Name 1-(1H-benzimidazol-2-yl)ethanone InChI…
Product Information Product Name Methyl 2-bromo-1H-benzimidazole-6-carboxylate Brand Name ChemScene Product Number CS-0783218 CAS 1092286-70-8 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 33778503 IUPAC Name methyl…
Product Information Product Name N-Ethylbenzimidazole Brand Name ChemScene Product Number CS-0206160 CAS 7035-68-9 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 485094 IUPAC Name 1-ethylbenzimidazole InChI…
Product Information Product Name Methyl 4-bromo-1H-benzimidazole-6-carboxylate Brand Name ChemScene Product Number CS-0210786 CAS 1354756-19-6 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 74890446 IUPAC Name methyl…
Product Information Product Name Ethyl 3-2-(4-carbamimidoylanilino)methyl-1-methylbenzimidazole-5-carbonyl-pyridin-2-ylaminopropanoate,hydrochloride, 95% Brand Name J&K Product Number 1215880 CAS 211914-50-0 SDS Document View/Download Certificate of Analysis (COA) Search COA not found General Information PubChem CID…
Dichloro[(S)-(-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(S)-(-)-2-(α;-(i-propyl)methanamine)-1H-benzimidazole]ruthenium(II), min. 95%
Product Information Product Name Dichloro(S)-(-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl(S)-(-)-2-(α;-(i-propyl)methanamine)-1H-benzimidazoleruthenium(II), min. 95% Brand Name US-Strem Product Number 44-0915 Certificate of Analysis (COA) Search COA not found Description Technical Note:1.Efficient ruthenium catalyst for asymmetric hydrogenation of…
Dichloro[(S)-(-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(S)-(-)-2-(α;-(t-butyl)methanamine)-1H-benzimidazole]ruthenium(II), min. 95%
Product Information Product Name Dichloro(S)-(-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl(S)-(-)-2-(α;-(t-butyl)methanamine)-1H-benzimidazoleruthenium(II), min. 95% Brand Name US-Strem Product Number 44-0925 Certificate of Analysis (COA) Search COA not found Description Technical Note:1. Efficient ruthenium catalyst for the hydrogenation…
Dichloro[(S)-(-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(S)-(-)-2-(α;-methylmethanamine)-1H-benzimidazole]ruthenium(II), min. 95%
Product Information Product Name Dichloro(S)-(-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl(S)-(-)-2-(α;-methylmethanamine)-1H-benzimidazoleruthenium(II), min. 95% Brand Name US-Strem Product Number 44-0905 CAS 1443051-87-3 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 121234180 IUPAC Name…
Product Information Product Name Methyl 4-Methyl-2-Propyl-1H-Benzimidazole-6-Carboxylate Brand Name Chem Impex Product Number 24386 CAS 152628-00-7 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 10130835 IUPAC Name…
Product Information Product Name N-Boc-2-hydroxybenzimidazole Brand Name Chem Impex Product Number 15028 CAS 161468-45-7 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 2756037 IUPAC Name tert-butyl…
Product Information Product Name Ethyl 1H-Benzimidazole-2-carboxylate Brand Name Chem Impex Product Number 26126 CAS 1865-09-4 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 12436923 IUPAC Name…
Product Information Product Name N-octylbenzimidazole, 98% Brand Name J&K Product Number 1789271 CAS 42032-46-2 Molecular Formula C15H22N2 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 1893437…
Product Information Product Name Benzimidazole Brand Name ChemScene Product Number CS-W019944 CAS 51-17-2 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 5798 IUPAC Name 1H-benzimidazole InChI…
Product Information Product Name 5-Methoxy-1H-benzimidazole-2-ylamine Brand Name ChemScene Product Number CS-W018649 CAS 6232-91-3 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 80384 IUPAC Name 6-methoxy-1H-benzimidazol-2-amine InChI…
Product Information Product Name 2-Bromobenzimidazole Brand Name ChemScene Product Number CS-B1157 CAS 54624-57-6 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 2776281 IUPAC Name 2-bromo-1H-benzimidazole InChI…
Product Information Product Name 6-Bromo-1-methyl-1H-benzimidazole-2-methanol Brand Name ChemScene Product Number CS-0865744 CAS 958863-32-6 Certificate of Analysis (COA) Search COA not found General Information PubChem CID 69185572 IUPAC Name (6-bromo-1-methylbenzimidazol-2-yl)methanol InChI…
![Ethyl 3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate,hydrochloride, 95%|1215880|211914-50-0](http://www.jk-sci.com/cdn/shop/files/13162d9a400563989940663720136643_250x_crop_center.jpg?v=1788002639)
![Dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl][(S)-(-)-2-(α;-(i-propyl)methanamine)-1H-benzimidazole]ruthenium(II), min. 95%|44-0915](http://www.jk-sci.com/cdn/shop/files/9232848eb36c2fc29ea8c80bca8985f1_250x_crop_center.jpg?v=1787928668)
![Dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl][(S)-(-)-2-(α;-(t-butyl)methanamine)-1H-benzimidazole]ruthenium(II), min. 95%|44-0925](http://www.jk-sci.com/cdn/shop/files/db0f35344f8be23735193d4886de5f3e_250x_crop_center.jpg?v=1787928662)
![Dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl][(S)-(-)-2-(α;-methylmethanamine)-1H-benzimidazole]ruthenium(II), min. 95%|44-0905|1443051-87-3](http://www.jk-sci.com/cdn/shop/files/bbdc6936c6f3a5ba6c215e53524fecdf_250x_crop_center.jpg?v=1787928675)
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