125-28-0

Basic information

• Product Name: DIHYDROCODEINE TRIFLUOROACETATE
• Synonyms: 4,5-alpha-epoxy-3-methoxy-17-methyl-morphinan-6-alpha-o;4,5alpha-Epoxy-3-methoxy-17-methylmorphinan-6alpha-ol;6-alpha-hydrocodol;6alpha-Hydrocodol;6-Hydroxy-3-methoxy-N-methyl-4,5-epoxymorphinan;7,8-dihydro-codein;7,8-Dihydrocodeine;8,14-Dihydroneopine
• CAS NO: 125-28-0
• Molecular Formula: C₁₈H₂₃NO₃
• Molecular Weight: 399.4
• EINECS: 204-732-3
• Mol File: 125-28-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 112-113°
• Boiling Point: bp15 248°
• Flash Point: 9℃
• Appearance: white crystalline needles
• Density: 1.1412 (rough estimate)
• Vapor Pressure: 2.48E-09mmHg at 25°C
• Refractive Index: 1.5740 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: DIHYDROCODEINE TRIFLUOROACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDROCODEINE TRIFLUOROACETATE(125-28-0)
• EPA Substance Registry System: DIHYDROCODEINE TRIFLUOROACETATE(125-28-0)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• Hazardous Substances Data: 125-28-0(Hazardous Substances Data)

Usage

Originator

Bicodein,Uquifa

Manufacturing Process

The codein was reduced by hydrogen in the presence catalyst Pt (or Pd, or Ni) and 7,8-dihydrocodein was obtained.To the 7,8-dihydrocodein tartaric acid was added and mixed, in the result 7,8- dihydrocodein bitartrate was obtained.

Therapeutic Function

Antitussive, Narcotic analgesic

Safety Profile

Poison by ingestion, intravenous, and subcutaneous routes. Human systemic effects by ingestion and subcutaneous routes: somnolence, miosis (pupillary constriction), and respiratory depression. An analgesic. Can cause drug dependency with repeated doses. When heated to decomposition it emits toxic fumes of NOx. See also CODEINE.

InChI:InChI=1/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3

Upstream product

• 125-29-1 Hydrocodone 
• 77-78-1 dimethyl sulfate 
• 27229-56-7 [3,5-bis(benzyloxy)-4-methoxyphenyl]methanol 
• 54186-44-6 1-(3,5-dibenzyloxy-4-methoxybenzyl)-6-methoxy-3,4-dihydroisoquinoline 
• 1402404-92-5 1,3-bis(benzyloxy)-5-(bromomethyl)-2-methoxybenzene 
• 67315-07-5 (+)-(R)-1-(3,5-dibenzyloxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 1423037-82-4 (7aR,12bS)-9-methoxy-3-methyl-4,4a,5,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-2,7-(3H,7aH)-dione 
• 1422971-69-4 C₁₉H₂₅NO₄ 
• 1422971-70-7 (4bS)-3,4-dimethoxy-11-methyl-8,8a,9,10-tetrahydro-7H-9,4b-(epiminoethano)phenanthren-12-one 
• 1422971-73-0 C₂₁H₃₁NO₆ 
• 40972-86-9 (2,3-dimethoxyphenyl)boronic acid 
• 1422971-72-9 C₃₀H₄₉NO₇Si 

Downstream Products

• 808-24-2 nicotinic acid 4,5α-epoxy-3-methoxy-17-methyl-morphinan-6α-yl ester 
• 845-69-2 Nordihydrocodeine 
• 1403776-88-4 4,5-epoxy-3-methoxy-17-methyl-(5α,6α)-morphinane-6-olbenzoate 
• 3861-72-1 dihydrocodeine-6-O-acetate 
• 125-29-1 Hydrocodone 
• 119931-40-7 C₂₃H₂₄N₂O₄S₂ 
• 509-60-4 dihydromorphine 

Relevant articles and documents

Practical and high-yield syntheses of dihydromorphine from tetrahydrothebaine and efficient syntheses of (8S)-8-bromomorphide

A practical method for the conversion of tetrahydrothebaine to dihydromorphine in 92% yield is described. The procedure should allow more efficient production of opium products and may be easily modified for large-scale synthesis. The conversion of codeine to (8S)-8-bromomorphide, a potentially valuable intermediate to 6-demethoxyoripavine and derivatives, is also described. The absolute configuration of (8S)-8-bromomorphide was determined by a single-crystal X-ray diffraction study of the hydrobromide salt.

A rapid, nearly quantitative conversion of codeine to hydrocodone

A very rapid, two-step, virtually quantitative synthesis of hydrocodone from codeine, via the intermediacy of dihydrocodeine, has been developed.

Programmed serial stereochemical relay and its application in the synthesis of morphinans

Herein we report a rationally designed, serial point-to-axial and axial-to-point stereoinduction and its integration into multi-step and target-oriented organic synthesis. In this proof-of-concept study, the configurational stability of several carefully designed atropisomeric intermediates and the fidelity of their unconventional stereoinductions were systematically investigated. The highly functionalized prepared synthetic intermediate was further applied in a novel chemical method to access the morphinans and it is potentially applicable to other structurally related alkaloids.

Enantioselective synthesis of (-)-dihydrocodeine and formal synthesis of (-)-thebaine, (-)-codeine, and (-)-morphine from a deprotonated α-aminonitrile

The α-benzylation of a deprotonated bicyclic α-aminonitrile, followed by Noyori's asymmetric transfer hydrogenation combined with the Grewe cyclization onto a symmetrical A-ring precursor, are the key steps of a short and high-yielding enantioselective synthesis of the morphinan (-)-dihydrocodeine. This compound can be converted to (-)-thebaine in high yield by known transformations, while (-)-codeine and (-)-morphine are available from an advanced intermediate. (Chemical Equation Presented).