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Dihydrocodeine

Note: Since these substances are related, please refer to Codeine Facts for more information on precautions, interactions, mechanism of action and effects.

Facts

Dihydrocodeine (DHC) is a synthetic opioid analgesic developed in the early 1900s. Its structure and pharmacokinetics are similar to that of codeine and it is used for the treatment of postoperative pain, severe breathlessness or as an antitussive.

Listen to the correct pronunciation of the word dihydrocodeine (compound).

Precautions

Related information: codeine precautions

Interactions

Related information: codeine interactions

Administration

Dihydrocodeine can be administered orally, intramuscularly, subcutaneously (skin popping) and rectally.

Dosage

Dihydrocodeine is approximately twice as potent as codeine; take this into consideration while dosing dihydrocodeine.

Related information: codeine dosage

Effects

The general effects profile is similar to that of codeine.

Metabolism

The cytochrome P450-2D6 (CYP2D6) is the major enzyme mediating O-demethylation of dihydrocodeine to dihydromorphine. In contrast, nordihydrocodeine formation is predominantly catalysed by cytochrome P450-3A (CYP3A).

The urinary secretion products consist of dihydronorcodeine, dihydromorphine, nordihydromorphine, dihydrocodeine glucuronide, and dihydronorcodeine-6-glucuronide. The major urinary metabolite is dihydrocodeine glucuronide (49%), and other metabolites are found to be in concentrations 0.1-3%.

Extraction

With dihydrocodeine tablets that may include other substances, such as paracetamol, the extraction method is usually the same as with codeine. Read the chemistry section below for more information.

Drug testing

Following the administration of dihydrocodeine, the following substances can be detected up to 48 hours after (depends upon the dose, its frequency, route of administration and urine excretion/dilution): dihydrocodeine and small quantities of dihydromorphine.

Opioids can be detected in urine, blood, bile, hair, nails and sweat.

Chemistry

Dihydrocodeine can be synthesised from morphine by reduction of the 7,8-double bond.

DHC 2D molecule
NameDihydrocodeine
Chemical name4,5-alpha-epoxy-3-methoxy-17-morphinan-6-ol
Alternative names6-hydroxy-3-methoxy-N-methyl-4,5-epoxymorphinan, 7,8-dihydro-codeine
CAS Number125-28-0
Chemical formulaC18H23NO3
Molecular weight301.42
Boiling point
Melting point
Flash point

NameDihydrocodeine tartrate
Chemical name4,5-alpha-epoxy-3-methoxy-17-morphinan-6-ol tartrate
Alternative namesdihydrocodeine acid tartrate, dihydrocodeine bitartrate
CAS Number5965-13-9
Chemical formulaC18H23NO3.C4H6O6
Molecular weight451.52
NameDihydrocodeine phosphate
Chemical name4,5-alpha-epoxy-3-methoxy-17-morphinan-6-ol phosphate
Alternative names(5-alpha,6-alpha)-4,5-epoxy-3-methoxy-17-methyl-morphinan-6-ol
CAS Number24204-13-5
Chemical formulaC18H21NO3.H3PO4
Molecular weight399.42

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