Dextrorphan: Difference between revisions

Dextrorphan
	File:Dextrorphan 2D.gif
Identifiers
	IUPAC name 17-methyl-9a,13a,14a-morphinan-3-ol;
CAS Number	125-73-5;
PubChem CID	5360697;
CompTox Dashboard (EPA)	DTXSID301014178 ;
ECHA InfoCard	100.004.323
Chemical and physical data
Formula	C17H23NO
Molar mass	257.371 g/mol g·mol−1

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Revision as of 06:59, 21 September 2007

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

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.

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 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[http://jpet.aspetjournals.org/cgi/content/full/309/2/515?ijkey=73c6efcf7713b02798c855b5ce4d50f1aa22d299&keytype2=tf_ipsecsha#ABS].
-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 caracteristic of NMDA blockade and which have afforded DM its potential for abuse as a recreational drug.
+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==