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Antitussive
Dextrorphan
Другие языки:

Dextrorphan

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Not to be confused with Dextromethorphan or Dextrallorphan.
Dextrorphan
Dextrorphan.svg
Dextrorphane 3d.gif
Clinical data
Other names DXO, Dextrorphanol
ATC code
  • None
Legal status
Legal status
  • US: Unscheduled
Identifiers
  • (+)-17-methyl-9a,13a,14a-morphinan-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.323
Chemical and physical data
Formula C17H23NO
Molar mass 257.377 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
 ☒NcheckY (what is this?)  (verify)

Dextrorphan (DXO) is a psychoactive drug of the morphinan class which acts as an antitussive or cough suppressant and 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.

Pharmacology

Pharmacodynamics

Dextrorphan
Site Ki (nM) Species Ref
NMDAR
(MK-801)		 486–906 Rat
σ1 118–481 Rat
σ2 11,325–15,582 Rat
MOR 420
>1,000		 Rat
Human
DOR 34,700 Rat
KOR 5,950 Rat
SERT 401–484 Rat
NET ≥340 Rat
DAT >1,000 Rat
5-HT1A >1,000 Rat
5-HT1B/1D 54% at 1 μM Rat
5-HT2A >1,000 Rat
α1 >1,000 Rat
α2 >1,000 Rat
β 35% at 1 μM Rat
D2 >1,000 Rat
H1 95% at 1 μM Rat
mAChRs 100% at 1 μM Rat
nAChRs 1,300–29,600
(IC50)		 Rat
VDSCs ND ND ND
Values are Ki (nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to the site.

The pharmacology of dextrorphan is similar to that of dextromethorphan (DXM). However, dextrorphan is much more potent as an NMDA receptor antagonist as well much less active as a serotonin reuptake inhibitor, but retains DXM's activity as a norepinephrine reuptake inhibitor. 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. It is further converted to 3-HM by CYP3A4 or glucuronidated.

Society and culture

Legal status

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

Research

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

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.

See also


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