Dextrorphan

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Dextrorphan (DX) is a pharmacologically active metabolite of dextromethorphan (DM, DXM).

Dextrorphan
Systematic (IUPAC) name
17-methyl-9a,13a,14a-morphinan-3-ol
Identifiers
CAS number 125-73-5
ATC code  ?
PubChem 5360697
Chemical data
Formula C17H23NO 
Mol. mass 257.371 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?
Legal status
Routes  ?

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 (CYP4502D6) pathway.

Being structurally similar to dextromethorphan, and it has affinity for the same receptors in the central nervous system but with a slight difference in selectivity.

Dextromethorphan is a weak non-competitive NMDA receptor antagonist but dextrorphan is a more potent antagonist[1]. DX is a strong anti-tussive[citation needed], but is slightly less effective than DM, and has no metabolites with significant therapeutic activity in such capacity and therefore is not a drug available on the market.

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 disassociation", which have afforded DM its potential for abuse as a recreational drug.


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