58772-72-8

Basic information

• Product Name: N,6-diacetylnormorphine
• Synonyms: N,6-diacetylnormorphine
• CAS NO: 58772-72-8
• Molecular Formula: C₂₀H₂₁NO₅
• Molecular Weight: 355.38444
• Mol File: 58772-72-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,6-diacetylnormorphine(CAS DataBase Reference)
• NIST Chemistry Reference: N,6-diacetylnormorphine(58772-72-8)
• EPA Substance Registry System: N,6-diacetylnormorphine(58772-72-8)

Safety Data

• Hazardous Substances Data: 58772-72-8(Hazardous Substances Data)

Upstream product

• 98673-60-0 C₂₁H₂₃NO₅ 
• 57934-02-8 C₂₃H₂₃NO₇ 
• 561-27-3 Diamorphine 
• 64-31-3 morphine sulfate 
• 466-97-7 normorphine 
• 57018-65-2 3-tert-butoxycarbonyloxy-4,5α-epoxy-6α-hydroxy-morphin-7-ene-17-carboxylic acid tert-butyl ester 
• 57-27-2 MORPHIN 
• 54260-60-5 2,2,2-trichloroethoxycarbonylnormorphine 
• 75-36-5 acetyl chloride 
• 58809-49-7 3,6α-diacetoxy-4,5α-epoxy-morphin-7-ene-17-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 108-24-7 acetic anhydride 
• 57018-66-3 4,5α-epoxy-3,6α-dihydroxy-morphin-7-ene-17-carboxylic acid tert-butyl ester 
• 1502-95-0 heroin hydrochloride 

Downstream Products

• 1313816-36-2 ((4aR,7S,7aR,12bS)-3-(3-(3-tritylthio)propanamido)butyl)-2,3,4,4a,7,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diyl diacetate 
• 466-97-7 normorphine 

Relevant articles and documents

Preparation and analgesic activity of 3,6 diacetylnormorphine and 6 acetylnormorphine

3,6 Diacetylnormorphine (norheroin) and 6 acetylnormorphine have been prepared in excellent yield through the 3,N bis (tert butoxycarbonyl) derivative of normorphine via acetylation and selective removal of protecting groups. This general procedure would be applicable to the preparation of various 3,6 diesters or 6 monoesters of normorphine. The analgesic potency of norheroin was found to be the same as that of 6 acetylnormorphine, about 0.05 that of heroin. The onset, peak, and duration of action of these compounds were nearly identical and comparable with morphine.

A chemically contiguous hapten approach for a heroin-fentanyl vaccine

Background: Increased death due to the opioid epidemic in the United States has necessitated the development of new strategies to treat addiction. Monoclonal antibodies and antidrug vaccines provide a tool that both aids addiction management and reduces the potential for overdose. Dual drug vaccines formulated by successive conjugation or by mixture have certain drawbacks. The current study examines an approach for combatting the dangers of fentanyl-laced heroin, by using a hapten with one epitope that has domains for both fentanyl and heroin. Results: We evaluated a series of nine vaccines developed from chemically contiguous haptens composed of both heroin- and fentanyl-like domains. Analysis of the results obtained by SPR and ELISA revealed trends in antibody affinity and titers for heroin and fentanyl based on epitope size and linker location. In antinociception studies, the best performing vaccines offered comparable protection against heroin as our benchmark heroin vaccine, but exhibited attenuated protection against fentanyl compared to our fentanyl vaccine. Conclusion: After thorough investigation of this strategy, we have identified key considerations for the development of a chemically contiguous heroin-fentanyl vaccine. Importantly, this is the first report of such a strategy in the opioid-drug-vaccine field.

6-ACETYLMORPHINE ANALOGS, AND METHODS FOR THEIR SYNTHESIS AND USE

The present invention relates to novel 6-acetylmorphine analogs, and methods for their synthesis and use. Such analogs are designed to provide a convenient linkage chemistry for coupling under mild conditions to a suitable group on a target protein, polypeptide, solid phase or detectable label.