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Dextrorphan

Psychoactive cough suppressant medication From Wikipedia, the free encyclopedia

Dextrorphan
Not to be confused with Dextromethorphan or Dextrallorphan.

Dextrorphan (DXO) is a psychoactive drug of the morphinan class which acts as an antitussive or cough suppressant and in high doses a dissociative hallucinogen. It is the dextrorotatory enantiomer of racemorphan; the levorotatory enantiomer is levorphanol. Dextrorphan is produced by O-demethylation of dextromethorphan by CYP2D6. Dextrorphan is an NMDA antagonist and contributes to the psychoactive effects of dextromethorphan.[2]

Quick Facts Clinical data, Other names ...
Dextrorphan
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Clinical data
Other namesDXO, Dextrorphanol
ATC code
  • None
Legal status
Legal status
  • US: Unscheduled[1]
Identifiers
  • (+)-17-methyl-9a,13a,14a-morphinan-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.323
Chemical and physical data
FormulaC17H23NO
Molar mass257.377 g·mol−1
3D model (JSmol)
  • CN1CC[C@@]23CCCC[C@@H]2[C@@H]1Cc4c3cc(O)cc4
  • InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1 N
  • Key:JAQUASYNZVUNQP-PVAVHDDUSA-N N
 NY (what is this?)  (verify)
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Pharmacology

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Perspective

Pharmacodynamics

More information Site, Ki (nM) ...
Dextrorphan[3][4][5][6]
SiteKi (nM)SpeciesRef
NMDAR
(MK-801)		486–906Rat[4]
σ1118–481Rat[4]
σ211,325–15,582Rat[4]
MORTooltip μ-Opioid receptor420
>1,000		Rat
Human		[4][7]
DORTooltip δ-Opioid receptor34,700Rat[4]
KORTooltip κ-Opioid receptor5,950Rat[4]
SERTTooltip Serotonin transporter401–484Rat[4]
NETTooltip Norepinephrine transporter≥340Rat[4]
DATTooltip Dopamine transporter>1,000Rat[4]
5-HT1A>1,000Rat[4]
5-HT1B/1D54% at 1 μMRat[4]
5-HT2A>1,000Rat[4]
α1>1,000Rat[4]
α2>1,000Rat[4]
β35% at 1 μMRat[4]
D2>1,000Rat[4]
H195% at 1 μMRat[4]
mAChRsTooltip Muscarinic acetylcholine receptors100% at 1 μMRat[4]
nAChRsTooltip Nicotinic acetylcholine receptors1,300–29,600
(IC50)		Rat[4]
VDSCsTooltip Voltage-dependent sodium channelsNDNDND
Values are Ki (nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to the site.
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The pharmacology of dextrorphan is similar to that of dextromethorphan (DXM). However, dextrorphan is much more potent as an NMDA receptor antagonist and much less active as a serotonin reuptake inhibitor, but retains DXM's activity as a norepinephrine reuptake inhibitor.[8] It also has more affinity for the opioid receptors than dextromethorphan, significantly so at high doses.

Pharmacokinetics

Dextrorphan has a notably longer elimination half-life than its parent compound, and therefore has a tendency to accumulate in the blood after repeated administration of normally dosed dextromethorphan formulations.[citation needed] It is further converted to 3-HM by CYP3A4 or glucuronidated.[9]

Society and culture

Dextrorphan was formerly a Schedule I controlled substance in the United States, but was unscheduled on October 1, 1976.[10]

Research

Dextrorphan was under development for the treatment of stroke, and reached phase II clinical trials for this indication, but development was discontinued.[11]

Environmental presence

In 2021, dextrorphan was identified in >75% of sludge samples taken from 12 wastewater treatment plants in California. The same study associated dextrorphan with estrogenic activity by using predictive modelling, before observing it in in vitro.[12]

See also

References

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