14357-78-9

Basic information

• Product Name: DIPRENORPHINE
• Synonyms: DIPRENORPHINE;DPN;6,14-ETHENOMORPHINAN-7-METHANOL, 17-(CYCLOPROPYLMETHYL)-4,5-EPOXY-18,19-DIHYDRO-3-HYDROXY-6-METHOXY-ALPHA, ALPHA-DIMETHYL-, (5ALPHA, 7ALPHA);DIPRENORPHINE POTENT OPIOID ANTAGON;Diprenorphine (base and/or unspecified salts);6,14-Ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-a,a-dimethyl-, (5a, 7a);(5α,7α)-17-(Cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-α,α-dimethyl-6,14-ethenomorphinan-7-methanol;17-(Cyclopropylmethyl)-4,5α-epoxy-3-hydroxy-α,α-dimethyl-6-methoxy-6β,14-ethanomorphinan-7α-methanol
• CAS NO: 14357-78-9
• Molecular Formula: C₂₆H₃₅NO₄
• Molecular Weight: 425.56
• EINECS: 238-325-7
• Mol File: 14357-78-9.mol

Chemical Properties

• Melting Point: 185°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.33 g/cm³
• Refractive Index: 1.656
• Storage Temp.: Store at RT
• CAS DataBase Reference: DIPRENORPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: DIPRENORPHINE(14357-78-9)
• EPA Substance Registry System: DIPRENORPHINE(14357-78-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 14357-78-9(Hazardous Substances Data)

Usage

Chemical Properties

Colourless or nearly colourless solid

Brand name

M50-50 Injection (Lemmon).

Biological Activity

Non-selective opioid receptor antagonist (K i values are 0.017, 0.072 and 0.23 nM for κ -, μ - and δ -opioid receptors).

InChI:InChI=1/C26H35NO4/c1-23(2,29)18-13-24-8-9-26(18,30-3)22-25(24)10-11-27(14-15-4-5-15)19(24)12-16-6-7-17(28)21(31-22)20(16)25/h6-7,15,18-19,22,28-29H,4-5,8-14H2,1-3H3/t18-,19-,22-,24-,25+,26-/m1/s1

Upstream product

• 16671-47-9 4,5α-epoxy-7α-(1-hydroxy-1-methyl-ethyl)-3,6-dimethoxy-6α,14α-ethano-morphinane-17-carbonitrile 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 16528-12-4 (5R,6R,7S,9R,13S,14S)-17-Cyclopropylmethyl-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,α-dimethyl-6,14-ethanomorphinan-7-methanol 
• 113729-34-3 3-(O-t-butyldimethylsilyl)-6-(O-desmethyl)-diprenorphine 
• 74-88-4 methyl iodide 
• 2579-67-1 northebaine 
• 99307-35-4 N-demethyl-N-formylthebaibe 
• 152518-97-3 (5R,6R,7S,9R,13S,14S)-7-Acetyl-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-6,14-ethanomorphinan 
• 152427-78-6 (5R,6R,7S,9R,13S,14R)-7-Acetyl-4,5-epoxy-17-formyl-3,6-dimethoxy-6,14-ethenomorphinan 
• 152518-96-2 (5R,6R,7S,9R,13S,14S)-7-Acetyl-4,5-epoxy-17-formyl-18,19-dihydro-3,6-dimethoxy-6,14-ethanomorphinan 
• 72221-15-9 N-Benzyl-northebain 
• 152427-77-5 (5R,6R,7S,9R,13S,14S)-7-Acetyl-17-cyclopropylmethyl-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-6,14-ethanomorphinan 
• 113707-18-9 6-O-desmethyl-diprenorphine 
• 115-37-7 thebaine 

Downstream Products

• 445289-66-7 3-O-[(Z)-4-(p-toluenesulfonyl)-but-2-enyl]diprenorphine 
• 445289-64-5 3-O-[(Z)-4-(tert-butyldiphenylsilyoxy)-but-2-enyl]diprenorphine 
• 1426174-15-3 (5R,6R,7R,9R,13S,14S)-(5α,7α)-17-cyclopropylmethyl4,5-epoxy-18,19-dihydro-6-(2-fluoroethoxy)-3-triphenylmethoxy-α,α-dimethyl-6,14-ethenomorphinan-7-methanol 

Related news

DIPRENORPHINE (cas 14357-78-9) as a stimulus in drug discrimination learning08/11/2019

Using the conditioned taste aversion baseline of drug discrimination learning, animals were trained to discriminate diprenorphine from distilled water. In subsequent generalization tests, the opiate antagonists naltrexone and naloxone and the mixed opiate agonist/antagonist nalorphine substitute...detailed

Morphine and DIPRENORPHINE (cas 14357-78-9) together potentiate intake of alcoholic beverages08/06/2019

Water-deprived rats were given a daily opportunity to take water or an ethanol solution. Prior to some opportunities to drink, some were injected with morphine (across procedures either 2.0, 7.5, or 20.0 mg/kg), diprenorphine (from 0.001 to 10.0 mg/kg), or a combination of diprenorphine and morp...detailed

Relevant articles and documents

PREPARATION OF OPIATE ANALGESICS BY REDUCTIVE ALKYLATION

A process for preparing a compound of formula (A), (B) or (C): wherein P is H, CH3 or a hydroxyl protecting group; X is O, a protected ketone, OH, a protected hydroxyl group or H; Y is OH, a protected hydroxyl group or H; W is C(CH3)2OH, C(CH3)(C(CH3)3)OH or COCH3; Z is C2-C10 alkyl or C2-C10 arylalkyl; and ′ is a. single bond or a double bond, is disclosed. The process is a reductive alkylation in the presence of hydrogen and a reductive alkylation catalyst.

Preparation of 6,14-Ethenomorphinane Derivatives

Buprenorphine (5j) and diprenorphine (5k) were synthesized from N-formyl-northebaine (1c) and N-benzyl-northebaine (1d) via new intermediates.N-cyclopropylmethyl-dihydronorthevinone 3d is a suitable compund for the synthesis of both 5j and 5k.We carried out detailed (1)H- and (13)C-NMR analysis of the new compounds. Key words: Buprenorphine; diprenorphine; rotamers, N-CHO; morphinane derivatives; alkaloids.

SYNTHESIS OF CARBON-11 LABELLED DIPRENORPHINE: A RADIOLIGAND FOR POSITRON EMISSION TOMOGRAPHIC STUDIES OF OPIATE RECEPTORS

Selective alkylation of 3-(O-t-butyldimethylsilyl)-6-(O-desmethyl)-diprenorphine with -methyl iodide followed by desilylation affords -diprenorphine labeled at the 6-methoxy position in 10percent yield with a specific activity of 1740 mCi/μmol at the end of a 30 minute synthesis.