1640-11-5

Upstream product

• 91742-67-5 2-(4-Nitro-phenyl)-1-(4-phenylimino-piperidin-1-yl)-ethanone 
• 79-03-8 propionyl chloride 
• 91742-69-7 1-<2-(4-nitrophenyl)ethyl>-4-(phenylamino)piperidine 
• 50434-36-1 4-nitrophenylacetyl chloride 
• 91742-68-6 1-<2-(4-nitrophenyl)acetyl>-4-(phenylamino)piperidine 
• 91742-66-4 1-<(4-nitrophenyl)acetyl>-4-piperidone 
• 62-53-3 aniline 
• 41979-39-9 4-piperidone hydrochloride 
• 123-62-6 propionic acid anhydride 

Downstream Products

• 1169-73-9 N-<1-<2-(4-aminophenyl)ethyl>-4-piperidinyl>-N-phenylpropanamide 

Relevant academic research and scientific papers

FENTANYL HAPTENS FOR THE PREPARATION OF A FENTANYL VACCINE

Described is the preparation of novel fentanyl haptens of Formula (1) through (6) and their use in the preparation of effective fentanyl vaccines.

Novel Vaccine That Blunts Fentanyl Effects and Sequesters Ultrapotent Fentanyl Analogues

Active immunization is an emerging potential modality to combat fatal overdose amid the opioid epidemic. In this study, we described the design, synthesis, formulation, and animal testing of an efficacious vaccine against fentanyl. The vaccine formulation is composed of a novel fentanyl hapten conjugated to tetanus toxoid (TT) and adjuvanted with liposomes containing monophosphoryl lipid A adsorbed on aluminum hydroxide. The linker and hapten N-phenyl-N-(1-(4-(3-(tritylthio)propanamido)phenethyl)piperidin-4-yl)propionamide were conjugated sequentially to TT using amine-N-hydroxysuccinimide-ester and thiol-maleimide reaction chemistries, respectively. Conjugation was facile, efficient, and reproducible with a protein recovery of >98% and a hapten density of 30-35 per carrier protein molecule. In mice, immunization induced high and robust antibody endpoint titers in the order of >106 against the hapten. The antisera bound fentanyl, carfentanil, cyclopropyl fentanyl, para-fluorofentanyl, and furanyl fentanyl in vitro with antibody-drug dissociation constants in the range of 0.36-4.66 nM. No cross-reactivity to naloxone, naltrexone, methadone, or buprenorphine was observed. In vivo, immunization shifted the antinociceptive dose-response curve of fentanyl to higher doses. Collectively, these preclinical results showcased the desired traits of a potential vaccine against fentanyl and demonstrated the feasibility of immunization to combat fentanyl-induced effects.

Method and kit for detecting, or determining the quantity of, metabolites of fentanyl and metabolites of fentanyl analogs

The invention provides an immunogen comprising a hapten coupled to an antigenicity-conferring carrier material, a conjugate comprising the aforementioned hapten coupled to a labelling agent, as well as, antibodies raised against the aforementioned immunogen and capable of binding with at least one structural epitope of metabolites of fentanyl and of metabolites of fentanyl analogs.

Probes for narcotic receptor mediated phenomena. 7. Synthesis and pharmacological properties of irreversible ligands specific for μ or δ opiate receptors

Syntheses of affinity reagents for opiate receptors based on the fentanyl, endo-ethenotetrahydrooripavine, and etonitazene carbon-nitrogen skeletons are described. The isothiocyanate, bromoacetamido, and methylfumaramido alkylating functions were employed