| 词条 | Levomethorphan |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 462091038 | IUPAC_name = (1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene | image = Levomethorphan.svg | image2 = Levometorfan.png | tradename = | MedlinePlus = | pregnancy_AU = | pregnancy_US = | legal_AU = S9 | legal_CA = Schedule I | legal_US = Schedule II | legal_UK = Class A | legal_DE = Anlage I | elimination_half-life = 3-6 hours | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 125-70-2 | ATC_prefix = None | PubChem = 5362449 | DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4642423 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7ZZ22K9QE6 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1908323 | C=18 | H=25 | N=1 | O=1 | molecular_weight = 271.397 g/mol | smiles = COc1ccc2C[C@@H]3[C@@H]4CCCC[C@]4(CCN3C)c2c1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = MKXZASYAUGDDCJ-CGTJXYLNSA-N }}Levomethorphan (INN, BAN) is an opioid analgesic of the morphinan family that has never been marketed.[1] It is the L-stereoisomer of racemethorphan (methorphan).[1] The effects of the two isomers of the racemethorphan are quite different, with dextromethorphan (DXM) contrarily being an antitussive at low doses and a dissociative hallucinogen at much higher doses.[2] It is about five times stronger than morphine. [3] Levomethorphan is a prodrug to levorphanol, analogously to DXM acting as a prodrug to dextrorphan or codeine behaving as a prodrug to morphine.[4] As such, levomethorphan has similar effects to levorphanol but is less potent as it must be demethylated to the active form by liver enzymes before being able to produce its effects.[4] As a prodrug of levorphanol, levomethorphan functions as a potent agonist of all three of the opioid receptors, μ, κ (κ1 and κ3 but notably not κ2), and δ, as an NMDA receptor antagonist, and as a serotonin-norepinephrine reuptake inhibitor.[4] Via activation of the KOR, levomethorphan can produce dysphoria and psychotomimetic effects such as dissociation and hallucinations.[5] Levomethorphan is listed under the Single Convention on Narcotic Drugs 1961 and is regulated like morphine in most countries. In the United States it is a Schedule II Narcotic controlled substance with a DEA ACSCN of 9210 and 2014 annual aggregate manufacturing quota of 195 grammes, up from 6 grammes the year before. The salts in use are the tartrate (free base conversion ratio 0.644) and hydrobromide (0.958).[6] At the current time, no levomethorphan pharmaceuticals are marketed in the United States. See also
References1. ^1 {{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA656|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=656–}} {{Analgesics}}{{Hallucinogens}}{{Analgesics}}{{Navboxes2. ^{{cite book|author=Joseph M. Hornback|title=Organic Chemistry|url=https://books.google.com/books?id=FETzRWMGt3YC&pg=PA243|date=31 January 2005|publisher=Cengage Learning|isbn=0-534-38951-1|pages=243–}} 3. ^[https://books.google.fi/books?id=3qjUKyL7BokC&pg=PA21&lpg=PA21&dq=Levomethorphan+potent+morphine&source=bl&ots=rHxOGAnHwu&sig=0ii5X6BFjpVGRlhpXcf-kfeFB88&hl=fi&sa=X&ved=0ahUKEwiegNGm54fRAhXEWiwKHfX7Dz0Q6AEILTAD#v=onepage&q=Levomethorphan%20potent%20morphine&f=false Handbook of Analytical Therapeutic Drug Monitoring and Toxicology] Google books preview 4. ^1 2 {{cite journal|last1=Gudin|first1=Jeffrey|last2=Fudin|first2=Jeffrey|last3=Nalamachu|first3=Srinivas|title=Levorphanol use: past, present and future|journal=Postgraduate Medicine|volume=128|issue=1|year=2015|pages=46–53|issn=0032-5481|doi=10.1080/00325481.2016.1128308}} 5. ^{{cite book|author1=Eduardo D. Bruera|author2=Russell K. Portenoy|title=Cancer Pain: Assessment and Management|url=https://books.google.com/books?id=2TJ-_oECXM4C&pg=PA215|date=12 October 2009|publisher=Cambridge University Press|isbn=978-0-521-87927-9|pages=215–}} 6. ^http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html | title = Pharmacodynamics | titlestyle = background:#ccccff | list1 ={{GABA receptor modulators}}{{Glycine receptor modulators}}{{Ionotropic glutamate receptor modulators}}{{Monoamine reuptake inhibitors}}{{Opioid receptor modulators}} }}{{analgesic-stub}} 14 : Delta-opioid agonists|Dissociative drugs|Enantiopure drugs|GABA receptor antagonists|Glycine receptor antagonists|Kappa agonists|NMDA receptor antagonists|Morphinans|Mu-opioid agonists|Nociceptin receptor agonists|Phenol ethers|Prodrugs|Semisynthetic opioids|Serotonin-norepinephrine reuptake inhibitors |
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