Dextrorphan
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Dextrorphan (DX) is a pharmacologically active metabolite of dextromethorphan (DM, DXM).
| Image:Dextrorphan 2D.gif | |
| Dextrorphan
| |
| Systematic (IUPAC) name | |
| 17-methyl-9a,13a,14a-morphinan-3-ol | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C17H23NO |
| Mol. mass | 257.371 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
Chemistry
It is the result of O-demethylation of the prodrug by several enzymatic systems, although it is chiefly a product of the Cytochrome P450 IID6 (CYP2D6) pathway.
Pharmacology
Dextrorphan is structurally similar to dextromethorphan, and has an affinity for the same receptors in the central nervous system, although with a slight difference in selectivity. While dextromethorphan is a weak non-competitive NMDA receptor antagonist, dextrorphan is a more potent antagonist[1].
It should be noted, however, that due to its potency as an NMDA receptor antagonist, as well as the fact that it is produced as a by-product of DM metabolization in the body, DX is thought to be largely responsible for the psychological side-effects that occur at high doses of DM. These side-effects can include alteration of consciousness, or "cognitive dissociation", which are characteristic of NMDA blockade and which have afforded DM its potential for abuse as a recreational drug.
See also
- Dextromethorphan
- Ketamine (compound that acts most similarly to dextrorphan)
- Hallucinogen
- Psychedelic
- Racemethorphan
- Morphinansfr:Dextrorphane
