Dextrorphan
Template:Short description Script error: No such module "Distinguish". Template:Short description <templatestyles src="Infobox drug/styles.css"/> Script error: No such module "Infobox".Template:Template otherScript error: No such module "TemplatePar".{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = | INN = | _drugtype =
| _has_physiological_data= | _has_gene_therapy=
| vaccine_type= | mab_type= | _number_of_combo_chemicals=Script error: No such module "ParameterCount". | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=172311CN1CC[C@@]23CCCC[C@@H]2[C@@H]1Cc4c3cc(O)cc41S/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/s1JAQUASYNZVUNQP-PVAVHDDUSA-NTemplate:StdinchiciteTemplate:Stdinchicite | _combo_data= | _physiological_data= | _clinical_data= None | _legal_data=Unscheduled[1]
| _other_data=(+)-17-methyl-9a,13a,14a-morphinan-3-ol
| _image_0_or_2 = Dextrorphan.svg | _image_LR =
| _datapage = Dextrorphan (data page) | _vaccine_target=_type_not_vaccine | _legal_all=Unscheduled[1] | _ATC_prefix_supplemental=None | _has_EMA_link = | CAS_number=125-73-5 | PubChem=5360697 | ChemSpiderID=10489895 | ChEBI= | ChEMBL=1254766 | DrugBank= | KEGG= | _hasInChI_or_Key=yes | UNII=04B7QNO9WS | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =
| _countSecondIDs=Script error: No such module "ParameterCount". | _countIndexlabels=Script error: No such module "ParameterCount". | _trackListSortletter= |QID = |QID2 = |Verifiedfields=changed |Watchedfields=changed |verifiedrevid=408496712}}
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
| Site | Ki (nM) | Species | Ref |
|---|---|---|---|
| NMDAR (MK-801) |
486–906 | Rat | [4] |
| σ1 | 118–481 | Rat | [4] |
| σ2 | 11,325–15,582 | Rat | [4] |
| MOR | 420 >1,000 |
Rat Human |
[4][7] |
| DOR | 34,700 | Rat | [4] |
| KOR | 5,950 | Rat | [4] |
| SERT | 401–484 | Rat | [4] |
| NET | ≥340 | Rat | [4] |
| DAT | >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] |
| mAChRs | 100% at 1 μM | Rat | [4] |
| nAChRs | 1,300–29,600 (IC50) |
Rat | [4] |
| 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 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
- Cough syrup
- Racemorphan; Levorphanol
- Noscapine
- Codeine; Pholcodine
- Dextromethorphan; Dimemorfan
- Butamirate
- Pentoxyverine
- Tipepidine
- Cloperastine
References
<templatestyles src="Reflist/styles.css" />
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ a b c d e f g h i j k l m n o p q r s t Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
Script error: No such module "Check for unknown parameters".
Template:Antitussives Script error: No such module "navboxes". Template:Drug use Template:DissociativesScript error: No such module "navboxes".Script error: No such module "Check for unknown parameters". Script error: No such module "navboxes". Template:Ionotropic glutamate receptor modulators Template:Monoamine reuptake inhibitors Template:Nicotinic acetylcholine receptor modulators Template:Opioid receptor modulators Template:Sigma receptor modulatorsScript error: No such module "navboxes".Script error: No such module "Check for unknown parameters".