Dextrorphan
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Dextrorphan (DXO) is a pharmacologically active metabolite of dextromethorphan (DXM).

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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.

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Legal status

Schedule I(US)

Routes  ?

Contents

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 DXM metabolization in the body, DXO is thought to be largely responsible for the psychological side-effects that occur at high doses of DXM. These side-effects can include alteration of consciousness, or "cognitive dissociation", which are characteristic of NMDA blockade and which have afforded DXM its potential for use as a recreational drug.

See also

  • Morphinan (parent drug of dextromethorphan)
    • Methorphan (racemic mixture of dextromethorphan and levomethorphan)
    • Dextromethorphan (DXM) (compound that breaks down into dextrorphan)
    • Levomethorphan (L-isomer of dextromethorphan with opioid activity)
    • Levorphanol (Metabolite of levomethorphan; levorphanol is the L-isomer of dextrorphan, has opioid activity)
  • Psychedelic (psychedelic experience)
  • Hallucinogen (drug that produces visual alterations and is commonly used for this purpose)
  • Psychedelic Drug (drug that is called 'mind expanding' and includes drugs like LSD)
    • Dissociatives (drug which reduces (or blocks) signals to the conscious mind from other parts of the brain)
      • Nitrous Oxide (short acting dissociative anesthetic that is inhaled for it's euphoric properties)
      • Ketamine (compound that acts most similarly to dextrorphan)
      • Dextromethorphan (DXM)
      • Dextrorphan (DXO)
      • Phencyclidine (PCP) (another compound that acts like dextrorphan)
  • Recreational use of dextromethorphan (use of dextromethorphan for purposes that induce effects caused by dextrorphan)

External links

Dextrorphan Legality

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