16196-82-0

Basic information

• Product Name: 1-[(5alpha,7alpha)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]ethanone
• Synonyms: 7α-Acetyl-6,14-endo-ethanotetrahydrothebaine;Hydrothevinone;1-[(5alpha,7alpha)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]ethanone;18,19-dihydrothevinone;1-[(4,5α-Epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan)-7α-yl]ethanone;1-((5alpha,7alpha)-4,5-Epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl)ethanone;Einecs 240-326-2;Dihydrothevinone
• CAS NO: 16196-82-0
• Molecular Formula: C₂₃H₂₉NO₄
• Molecular Weight: 382.47272
• EINECS: 240-326-2
• Product Categories: Amines;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 16196-82-0.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 518.1°Cat760mmHg
• Flash Point: 267.1°C
• Appearance: /
• Density: 1.29g/cm³
• CAS DataBase Reference: 1-[(5alpha,7alpha)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(5alpha,7alpha)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]ethanone(16196-82-0)
• EPA Substance Registry System: 1-[(5alpha,7alpha)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]ethanone(16196-82-0)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 16196-82-0(Hazardous Substances Data)

Usage

Uses

Intermediate in the preparation of Buprenorphine derivatives and analgesic compounds.

Upstream product

• 16196-83-1 7α-acetyl-6,14-endoethanotetrahydrothebaine 
• 757950-17-7 N-carboethoxythebaine 
• 36397-12-3 N-desmethyl-N-carboethoxycodeine 
• 16180-14-6 (S)-1-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-ethanol 
• 162333-22-4 (S)-1-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-ethano-morphinan-7α-yl)-ethanol 
• 60342-45-2 N-(ethoxycarbonyl)norcodeinone 
• 76-57-3 codeine 
• 115-37-7 thebaine 
• 15358-22-2 thevinone 

Downstream Products

• 151213-14-8 (5R,6R,7R,9R,13S,14S,20R)-4,5-Epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-α-phenyl-6,14-ethenomorphinan-7-methanol 
• 14357-78-9 diprenorphine 
• 22152-80-3 [5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol 
• 14357-76-7 Dihydroetorphine 
• 52485-79-7 Buprenorphine 
• 78715-23-8 norbuprenorphine 
• 84712-92-5 (2S)-2-[(5R,6R,7R,14S)-N-cyclopropanoyl-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol 
• 136232-95-6 buprenorphine hydrochloride 
• 136232-95-6 (+)-Buprenorphine hydrochloride 
• 152427-77-5 N-cylcopropylmethyl-6,14-endo-ethanonorthevinone 
• 1429120-69-3 C₃₃H₄₇NO₄ 
• 1429173-80-7 (2′R,5α,6R,7R,14α)-2′-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethano-morphinan-7-yl)-4′-cyclohexyl-butan-2′-ol 
• 736131-85-4 (2′R,5α,6R,7R,14α)-2′-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethano-morphinan-7-yl)-3′-cyclohexyl-propan-2′-ol 
• 136232-95-6 Buprenorphin Hydrochlorid 

Relevant articles and documents

A highly selective κ-opioid receptor agonist with low addictive potential and dependence liability

Buprenorphine analogs have been synthesized. In the studies of analgesic and addictive effects in mice and [35S]GTPγS binding assay in human brain tissue, an analog of buprenorphine where the tert-butyl is replaced by a cyclobutyl moiety (16) has been identified as a selective κ-partial agonist which gives antinociceptive effects, but has low abuse potential. The results may lead to lower degrees of dysphoria than full κ-agonists.

DEUTERATED COMPOUND AND MEDICAL USE THEREOF

The present invention relates to a compound represented by formula I and a non-toxic pharmaceutically acceptable salt thereof. In formula (I), R1 is H, CH3 or deuterated methyl (CD3); R2 is CH3 or CH2CH3; R3, R4 and R5 are each independently H or deuterium (D); when R1 is H or CH3, at least one of R3, R4 and R5 is D.

Industrial process for the preparation of buprenorphine and its intermediates

There is provided an efficient industrial process for the preparation of 21-cyclopropyl-7a-(2-hydroxy-3,3-dimethyl-2-butyl)-6,14-endo-ethano-6,7,8,14-tetrahydro-oripavine,i.e. buprenorphine of Formula- I in high yield and purity, with enhanced safety and eco-friendly norms. The invention further relates to an improved process for preparation of intermediates thereof in high yield and purity.