Dextrorphan: Difference between revisions

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| image              = Dextrorphan.svg
| image              = Dextrorphan.svg
| image_class        = skin-invert-image
| image_class        = skin-invert-image
| image2            = Dextrorphane 3d.gif


<!--Clinical data-->| tradename          =  
<!--Clinical data-->| tradename          =  
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===Pharmacodynamics===
===Pharmacodynamics===
{| class="wikitable floatleft" style="font-size:small;"
{| class="wikitable floatleft" style="font-size:small;"
|+ Dextrorphan<ref name="PDSP">{{cite web | title = PDSP K<sub>i</sub> Database | work = Psychoactive Drug Screening Program (PDSP)|author1-link=Bryan Roth| vauthors = Roth BL, Driscol J | publisher = University of North Carolina at Chapel Hill and the United States National Institute of Mental Health | access-date = 14 August 2017 | url = https://pdsp.unc.edu/databases/pdsp.php?knowID=0&kiKey=&receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=dextrorphan&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query}}</ref><ref name="pmid26826604">{{cite journal | vauthors = Nguyen L, Thomas KL, Lucke-Wold BP, Cavendish JZ, Crowe MS, Matsumoto RR | title = Dextromethorphan: An update on its utility for neurological and neuropsychiatric disorders | journal = Pharmacol. Ther. | volume = 159 | pages = 1–22 | year = 2016 | pmid = 26826604 | doi = 10.1016/j.pharmthera.2016.01.016 }}</ref><ref name="pmid17689532">{{cite journal | vauthors = Werling LL, Keller A, Frank JG, Nuwayhid SJ | title = A comparison of the binding profiles of dextromethorphan, memantine, fluoxetine and amitriptyline: treatment of involuntary emotional expression disorder | journal = Exp. Neurol. | volume = 207 | issue = 2 | pages = 248–57 | year = 2007 | pmid = 17689532 | doi = 10.1016/j.expneurol.2007.06.013 | s2cid = 38476281 }}</ref><ref name="pmid27139517">{{cite journal | vauthors = Taylor CP, Traynelis SF, Siffert J, Pope LE, Matsumoto RR | title = Pharmacology of dextromethorphan: Relevance to dextromethorphan/quinidine (Nuedexta®) clinical use | journal = Pharmacol. Ther. | volume = 164 | pages = 170–82 | year = 2016 | pmid = 27139517 | doi = 10.1016/j.pharmthera.2016.04.010 | doi-access = free }}</ref>
|+ Dextrorphan<ref name="PDSP">{{cite web | title = PDSP K<sub>i</sub> Database | work = Psychoactive Drug Screening Program (PDSP)|author1-link=Bryan Roth| vauthors = Roth BL, Driscol J | publisher = University of North Carolina at Chapel Hill and the United States National Institute of Mental Health | access-date = 14 August 2017 | url = https://pdsp.unc.edu/databases/pdsp.php?knowID=0&kiKey=&receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=dextrorphan&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query}}</ref><ref name="pmid26826604">{{cite journal | vauthors = Nguyen L, Thomas KL, Lucke-Wold BP, Cavendish JZ, Crowe MS, Matsumoto RR | title = Dextromethorphan: An update on its utility for neurological and neuropsychiatric disorders | journal = Pharmacol. Ther. | volume = 159 | pages = 1–22 | year = 2016 | pmid = 26826604 | doi = 10.1016/j.pharmthera.2016.01.016 | doi-access = free }}</ref><ref name="pmid17689532">{{cite journal | vauthors = Werling LL, Keller A, Frank JG, Nuwayhid SJ | title = A comparison of the binding profiles of dextromethorphan, memantine, fluoxetine and amitriptyline: treatment of involuntary emotional expression disorder | journal = Exp. Neurol. | volume = 207 | issue = 2 | pages = 248–57 | year = 2007 | pmid = 17689532 | doi = 10.1016/j.expneurol.2007.06.013 | s2cid = 38476281 }}</ref><ref name="pmid27139517">{{cite journal | vauthors = Taylor CP, Traynelis SF, Siffert J, Pope LE, Matsumoto RR | title = Pharmacology of dextromethorphan: Relevance to dextromethorphan/quinidine (Nuedexta®) clinical use | journal = Pharmacol. Ther. | volume = 164 | pages = 170–82 | year = 2016 | pmid = 27139517 | doi = 10.1016/j.pharmthera.2016.04.010 | doi-access = free }}</ref>
|-
|-
! Site !! K<sub>i</sub> (nM) !! Species !! Ref
! Site !! K<sub>i</sub> (nM) !! Species !! Ref
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| [[Sigma-2 receptor|σ<sub>2</sub>]] || 11,325–15,582 || Rat || <ref name="pmid26826604" />
| [[Sigma-2 receptor|σ<sub>2</sub>]] || 11,325–15,582 || Rat || <ref name="pmid26826604" />
|-
|-
| {{abbrlink|MOR|μ-Opioid receptor}} || 420<br />&gt;1,000 || Rat<br />Human || <ref name="pmid26826604" /><ref name="pmid7815359">{{cite journal | vauthors = Raynor K, Kong H, Mestek A, Bye LS, Tian M, Liu J, Yu L, Reisine T | title = Characterization of the cloned human mu opioid receptor | journal = J. Pharmacol. Exp. Ther. | volume = 272 | issue = 1 | pages = 423–8 | year = 1995 | pmid = 7815359 }}</ref>
| {{abbrlink|MOR|μ-Opioid receptor}} || 420<br />&gt;1,000 || Rat<br />Human || <ref name="pmid26826604" /><ref name="pmid7815359">{{cite journal | vauthors = Raynor K, Kong H, Mestek A, Bye LS, Tian M, Liu J, Yu L, Reisine T | title = Characterization of the cloned human mu opioid receptor | journal = J. Pharmacol. Exp. Ther. | volume = 272 | issue = 1 | pages = 423–8 | year = 1995 | doi = 10.1016/S0022-3565(25)24351-8 | pmid = 7815359 }}</ref>
|-
|-
| {{abbrlink|DOR|δ-Opioid receptor}} || 34,700 || Rat || <ref name="pmid26826604" />
| {{abbrlink|DOR|δ-Opioid receptor}} || 34,700 || Rat || <ref name="pmid26826604" />
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* [[Tipepidine]]
* [[Tipepidine]]
* [[Cloperastine]]
* [[Cloperastine]]
* [[Levocloperastine]]


==References==
==References==
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| list1 =  
{{Drug use}}
{{Drug use}}
{{Hallucinogens}}
{{Dissociatives}}
}}
}}
{{Navboxes
{{Navboxes
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[[Category:Sigma agonists]]
[[Category:Sigma agonists]]
[[Category:Human drug metabolites]]
[[Category:Human drug metabolites]]
[[Category:Recreational drug metabolites]]

Latest revision as of 00:25, 27 December 2025

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| _other_data=(+)-17-methyl-9a,13a,14a-morphinan-3-ol

| _image_0_or_2 = Dextrorphan.svg | _image_LR =

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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]

Pharmacology

Pharmacodynamics

Dextrorphan[3][4][5][6]
Site Ki (nM) Species Ref
NMDAR
(MK-801)		 486–906 Rat [4]
σ1 118–481 Rat [4]
σ2 11,325–15,582 Rat [4]
MORTooltip μ-Opioid receptor 420
>1,000		 Rat
Human		 [4][7]
DORTooltip δ-Opioid receptor 34,700 Rat [4]
KORTooltip κ-Opioid receptor 5,950 Rat [4]
SERTTooltip Serotonin transporter 401–484 Rat [4]
NETTooltip Norepinephrine transporter ≥340 Rat [4]
DATTooltip Dopamine transporter >1,000 Rat [4]
5-HT1A >1,000 Rat [4]
5-HT1B/1D 54% at 1 μM Rat [4]
5-HT2A >1,000 Rat [4]
α1 >1,000 Rat [4]
α2 >1,000 Rat [4]
β 35% at 1 μM Rat [4]
D2 >1,000 Rat [4]
H1 95% at 1 μM Rat [4]
mAChRsTooltip Muscarinic acetylcholine receptors 100% at 1 μM Rat [4]
nAChRsTooltip Nicotinic acetylcholine receptors 1,300–29,600
(IC50)		 Rat [4]
VDSCsTooltip Voltage-dependent sodium channels 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 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.Script error: No such module "Unsubst". It is further converted to 3-HM by CYP3A4 or glucuronidated.[9]

Society and culture

Legal status

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

<templatestyles src="Reflist/styles.css" />

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