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Dihydrocodeine: Difference between revisions
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>ExistingEntity Binding affinities, btw dihydromorphine deserves a page |
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Dihydrocodeine is used as an alternative or adjunct to [[codeine]] and is similar in chemical structure. Depending on individual metabolism, dihydrocodeine is 100 to 150 percent as strong as codeine. | Dihydrocodeine is used as an alternative or adjunct to [[codeine]] and is similar in chemical structure. Depending on individual metabolism, dihydrocodeine is 100 to 150 percent as strong as codeine. | ||
==Chemistry== | ==Chemistry== | ||
Dihydrocodeine, or 4,5-alpha-epoxy-3-methoxy-17-methylmorphinan-6-ol, is an opioid of the morphinan class. Dihydrocodeine and other molecules of this class contain a polycyclic core of three benzene rings fused in a zig-zag pattern called a phenanthrene. A fourth nitrogen containing ring is fused to the phenanthrene at R<sub>9</sub> and R<sub>13</sub> with the nitrogen member looking at R<sub>17</sub> of the combined structure. This structure is called morphinan. | Dihydrocodeine, or 4,5-alpha-epoxy-3-methoxy-17-methylmorphinan-6-ol, is an opioid of the morphinan class. Dihydrocodeine and other molecules of this class contain a polycyclic core of three benzene rings fused in a zig-zag pattern called a phenanthrene. A fourth nitrogen containing ring is fused to the phenanthrene at R<sub>9</sub> and R<sub>13</sub> with the nitrogen member looking at R<sub>17</sub> of the combined structure. This structure is called morphinan. | ||
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Dihydrocodeine is metabolized via CYP2D6 to the active metabolite dihydromorphine, which has a potency similar to morphine. Other weakly active metabolites include nordihydrocodeine (which is formed via CYP3A4) and dihydrocodeine-6-glucuronide.<ref>Kirkwood LC, Nation RL, Somogyi AA. Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine. Br J Clin Pharmacol. 1997;44:549-55.</ref> Although dihydrocodeine does have extremely active metabolites in the form of dihydromorphine and dihydromorphine-6-glucuronide, these metabolites are produced in such a small amount that they do not have clinically important effects.<ref>The role of active metabolites in dihydrocodeine effects (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/12665158</ref> | Dihydrocodeine is metabolized via CYP2D6 to the active metabolite dihydromorphine, which has a potency similar to morphine. Other weakly active metabolites include nordihydrocodeine (which is formed via CYP3A4) and dihydrocodeine-6-glucuronide.<ref>Kirkwood LC, Nation RL, Somogyi AA. Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine. Br J Clin Pharmacol. 1997;44:549-55.</ref> Although dihydrocodeine does have extremely active metabolites in the form of dihydromorphine and dihydromorphine-6-glucuronide, these metabolites are produced in such a small amount that they do not have clinically important effects.<ref>The role of active metabolites in dihydrocodeine effects (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/12665158</ref> | ||
===Binding affinities (K<sub>i</sub>)=== | |||
* Mu opioid agonist - 325 nM<ref>Affinities of Dihydrocodeine and its Metabolites to Opioid Receptors - Helmut Schmidt et al. (August 2002) | http://onlinelibrary.wiley.com/doi/10.1034/j.1600-0773.2002.910203.x/full</ref> | |||
* Kappa opioid agonist - 14242 nM<ref>Affinities of Dihydrocodeine and its Metabolites to Opioid Receptors - Helmut Schmidt et al. (August 2002) | http://onlinelibrary.wiley.com/doi/10.1034/j.1600-0773.2002.910203.x/full</ref> | |||
* Delta opioid agonist - 5905 nM<ref>Affinities of Dihydrocodeine and its Metabolites to Opioid Receptors - Helmut Schmidt et al. (August 2002) | http://onlinelibrary.wiley.com/doi/10.1034/j.1600-0773.2002.910203.x/full</ref> | |||
Dihydrocodeine itself is a weak ligand for the opioid receptors however its main active metabolite - [[dihydromorphine]] and one of its metabolites - dihydromorphine-6-O-glucuronide show much stronger agonistic effects.<ref>Affinities of Dihydrocodeine and its Metabolites to Opioid Receptors - Helmut Schmidt et al. (August 2002) | http://onlinelibrary.wiley.com/doi/10.1034/j.1600-0773.2002.910203.x/full</ref> | |||
==Subjective effects== | ==Subjective effects== | ||
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In comparison to [[codeine]], this compound can be generally described as significantly more euphoric and with less itchiness. | In comparison to [[codeine]], this compound can be generally described as significantly more euphoric and with less itchiness. | ||
===Physical effects=== | ===Physical effects=== | ||
*'''[[Effect::Pain relief]]''' | *'''[[Effect::Pain relief]]''' | ||
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*'''[[Effect::Compulsive redosing]]''' | *'''[[Effect::Compulsive redosing]]''' | ||
*'''[[Effect::Dream potentiation]]''' | *'''[[Effect::Dream potentiation]]''' | ||
===Experience reports=== | ===Experience reports=== | ||
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here: | There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here: | ||