| 词条 | Dextrorphan | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 408496712 | IUPAC_name = (+)-17-methyl-9a,13a,14a-morphinan-3-ol | image = Dextrorphan.svg | image2 = Dextrorphane 3d.gif | tradename = | legal_US = Unscheduled | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 125-73-5 | ATC_prefix = None | PubChem = 5360697 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = 04B7QNO9WS | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 341216 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 10489895 | synonyms = DXO | C=17 | H=23 | N=1 | O=1 | molecular_weight = 257.371 g/mol | SMILES = OC1=CC2=C(C[C@@H]3N(CC[C@@]42CCCC[C@H]34)C)C=C1 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = JAQUASYNZVUNQP-PVAVHDDUSA-N }}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-stereoisomer of racemorphan, the levo-half being levorphanol. Dextrorphan is produced by O-demethylation of dextromethorphan by CYP2D6. Dextrorphan is an NMDA antagonist and contributes to the psychoactive effects of dextromethorphan.[1] PharmacologyPharmacodynamics
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.[7] PharmacokineticsDextrorphan 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|date=November 2016}} Society and cultureLegal statusDextrorphan was formerly a Schedule I controlled substance in the United States, but was unscheduled on October 1, 1976.[8] ResearchDextrorphan was under development for the treatment of stroke, and reached phase II clinical trials for this indication, but development was discontinued.[9] {{Clear}}References1. ^{{cite journal | last1 = Zawertailo | first1 = L. A. | last2 = Kaplan | first2 = H. L. | last3 = Busto | first3 = U. E. | last4 = Tyndale | first4 = R. F. | last5 = Sellers | first5 = E. M. | title = Psychotropic Effects of Dextromethorphan are Altered by the CYP2D6 Polymorphism: A Pilot Study | pmid = 9690700 | journal = Journal of Clinical Psychopharmacology | volume = 18 | issue = 4 |date=Aug 1998 | pages = 332–337 | doi = 10.1097/00004714-199808000-00014 }} {{Antitussives}}{{Navboxes2. ^{{cite web | title = PDSP Ki Database | work = Psychoactive Drug Screening Program (PDSP) | author1 = Roth, BL | author2 = Driscol, J | publisher = University of North Carolina at Chapel Hill and the United States National Institute of Mental Health | accessdate = 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}} 3. ^1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 {{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 | issue = | pages = 1–22 | year = 2016 | pmid = 26826604 | doi = 10.1016/j.pharmthera.2016.01.016 | url = }} 4. ^{{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 | url = }} 5. ^{{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 | issue = | pages = 170–82 | year = 2016 | pmid = 27139517 | doi = 10.1016/j.pharmthera.2016.04.010 | url = }} 6. ^{{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 | doi = | url = }} 7. ^{{ cite journal | url = http://jpet.aspetjournals.org/content/309/2/515.full.pdf | format = pdf | title = Comparison of the Effects of Dextromethorphan, Dextrorphan, and Levorphanol on the Hypothalamo-Pituitary-Adrenal Axis |author1=Pechnick, R. N. |author2=Poland, R. E. | year = 2004 | volume = 309 | issue = 2 | pages = 515–522 | journal = Journal of Pharmacology and Experimental Therapeutics | doi = 10.1124/jpet.103.060038 | pmid = 14742749 }} 8. ^{{cite web | url = http://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf | title = Lists of: Scheduling Actions Controlled Substances Regulated Chemicals | author = DEA | accessdate = 2010-09-24}} 9. ^http://adisinsight.springer.com/drugs/800009336 | title = Recreational uses | titlestyle = background:#ccccff | list1 ={{Drug use}}{{Hallucinogens}} }}{{Navboxes | title = Pharmacodynamics | titlestyle = background:#ccccff | list1 ={{Ionotropic glutamate receptor modulators}}{{Monoamine reuptake inhibitors}}{{Nicotinic acetylcholine receptor modulators}}{{Opioid receptor modulators}}{{Sigma receptor modulators}} }} 11 : Antitussives|Dissociative drugs|Enantiopure drugs|Euphoriants|Morphinans|Mu-opioid agonists|Nicotinic antagonists|NMDA receptor antagonists|Phenols|Serotonin-norepinephrine reuptake inhibitors|Sigma agonists |
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