4829-46-3

Basic information

• Product Name: 14-HYDROXYCODEINE
• Synonyms: 4,5α-Epoxy-17-methyl-3-methoxy-7,8-didehydromorphinan-6α,14-diol;7,8-Didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α,14-diol;14-Hydroxycodeine (7,8-Didehydro-4,5a-epoxy-3-methoxy-17-methylmorphinan-6a,14-diol);7,8-DIDEHYDRO-4,5A-EPOXY-3-METHOXY-17-METHYLMORPHINAN-6A,14-DIOL;14-HYDROXYCODEINE;CODEINE IMP F;14-Hydroxycodene;(5R,6S)-3-Methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6,14-diol
• CAS NO: 4829-46-3
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.36
• Mol File: 4829-46-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 155-157 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• Boiling Point: 506.3 °C at 760 mmHg
• Flash Point: 260 °C
• Appearance: /
• Density: 1.43 g/cm³
• Vapor Pressure: 4.48E-11mmHg at 25°C
• Refractive Index: 1.694
• PKA: 12.93±0.40(Predicted)
• CAS DataBase Reference: 14-HYDROXYCODEINE(CAS DataBase Reference)
• NIST Chemistry Reference: 14-HYDROXYCODEINE(4829-46-3)
• EPA Substance Registry System: 14-HYDROXYCODEINE(4829-46-3)

Safety Data

• Hazardous Substances Data: 4829-46-3(Hazardous Substances Data)

Usage

Semi-synthetic opioid analgesic

A type of pain-relieving medication derived from a natural source but chemically modified to enhance its effects.

Antitussive medication

A medication used to suppress or reduce coughing.

Synthesized from codeine

14-HYDROXYCODEINE is created by chemically modifying codeine, a naturally occurring opioid found in the opium poppy plant.

Prodrug

14-HYDROXYCODEINE is a prodrug, meaning it is converted into its active form, hydromorphone, in the body.

Active form

Hydromorphone, a more potent opioid analgesic.

Potency

Approximately 5-10 times more potent than codeine.

Effects

Similar to codeine, including pain relief and cough suppression.

Uses

Typically used to treat moderate to severe pain and in some cases, for the management of coughing.

Potential for abuse and dependence

Like other opioids, 14-HYDROXYCODEINE has the potential for abuse and dependence.

Caution and supervision

Should be used with caution and under the supervision of a healthcare professional.

InChI:InChI=1/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-6,11,13,16,20-21H,7-9H2,1-2H3/t11-,13?,16-,17?,18?/m0/s1

Upstream product

• 508-54-3 14-hydroxycodeinone 
• 76-57-3 codeine 
• 115-37-7 thebaine 
• 5140-31-8 (+)-14β-bromocodeinone 
• 103458-67-9 14-hydroxycodeine diacatate 
• 100740-63-4 6α-acetoxy-4,5α-epoxy-3-methoxy-17-methyl-morphin-7-en-14-ol 
• 4675-05-2 (+)-14β-bromocodeine 

Downstream Products

• 41303-65-5 14-acetoxy-4,5α-epoxy-3-methoxy-17-methyl-6α-(toluene-4-sulfonyloxy)-morphin-7-ene 
• 7239-97-6 3-methoxy-4,5α-epoxy-6,7-didehydro-8α-acetoxy-14-hydroxy-17-methylmorphinan 
• 7387-55-5 14-Hydroxy-deoxydihydrocodein 
• 107277-81-6 14-acetoxy-4,5α-epoxy-3-methoxy-17-methyl-6α-(toluene-4-sulfonyloxy)-morphinane 
• 38211-20-0 4,5α-epoxy-3-methoxy-17-methyl-6α-(toluene-4-sulfonyloxy)-morphinan-14-ol 
• 909-94-4 14-Butyryloxycodeinon 
• 981-01-1 14-Propionyloxycodeinon 
• 1250-84-6 14-Valeryloxy-kodeinon 
• 94713-16-3 4,5α-epoxy-3-methoxy-17-methyl-(14ξ)-morphin-6-en-8-one 
• 76-42-6 Oxycodone 
• 2183-56-4 alpha-Oxymorphol 
• 142729-55-3 C₂₅H₂₅NO₅ 
• 7183-69-9 14-hydroxydihydrocodeine 
• 508-54-3 14-hydroxycodeinone 

Relevant articles and documents

Studies in the field of microbiological decomposition. XVII. Transformation of alkaloids in the morphine series by Trametes sanguinea. (2)

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Biotransformations of morphine alkaloids by fungi: N-demethylations, oxidations, and reductions

Morphine alkaloids and some of its derivatives (morphine, codeine, thebaine, oripavine, hydrocodone, and oxycodone) were subjected to fermentations with six fungal strains. The alkaloids were transformed to a variety of products via biological oxidations, reductions, and oxidative demethylations. The strain Cunninghamella echinulata proved to be the most effective for demethylations of all of the above compounds, except for morphine. The time profile of the conversion of 3-[14CH3]thebaine to 3-[ 14CH3]northebaine by C. echinulata cultures was also determined.

Transformations of morphine, codeine and their analogues by Bacillus sp

A bacterial strain belonging to the genus Bacillus islolated by enrichment culture technique using morphine as a sole source of carbon transforms morphine and codeine into 14-hydroxymorphinone and 14-hydroxycodeinone as major and 14-hydroxymorphine and 14-hydroxycodeine as minor metabolites, respectively. When the N-methyl group in morphine and codeine are replaced by higher alkyl groups, the organism still retains its ability to carry out 14-hydroxylation as well as oxidation of the C6-hydroxyl group in these N-variants, although the level of metabolites formed are considerably low. The organism readily transforms dihydromorphine and dihydrocodeine into only dihydromorphinone and dihydrocodeinone, respectively, suggesting that the 7,8-double bond is a necessary structural feature to carry out 14-hydroxylation reaction. The cell free extract (20,000 × g supernatant), prepared from morphine grown cells, transforms morphine into 14-hydroxymorphinone in the presence of NAD+, but fails to show activity against testosterone. However, the cell free extract prepared from testosterone grown cells contains significant levels of 17β- hydroxysteroid dehydrogenase but shows no activity against morphine.