# Levomethorphan

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Levomethorphan
> Markdown URL: https://mediated.wiki/source/Levomethorphan.md
> Source: https://en.wikipedia.org/wiki/Levomethorphan
> Source revision: 1354337753
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Opioid analgesic}}
{{dist|Dextromethorphan|Dextrorphan|3-Methoxymorphinan}}
{{Drugbox
| Verifiedfields     = changed
| Watchedfields      = changed
| verifiedrevid      = 462091038
| IUPAC_name         = (1''R'',9''R'',10''R'')-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0<sup>1</sup>,<sup>10</sup>.0<sup>2</sup>,<sup>7</sup>]heptadeca-2(7),3,5-triene
| image              = Levomethorphan.svg
| image_class        = skin-invert-image
| image2             = Levometorfan.png
| image_class2       = bg-transparent

<!--Clinical data-->| tradename          = 
| MedlinePlus        = 
| pregnancy_AU       = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US       = <!-- A / B / C / D / X -->
| legal_AU           = S9
| legal_BR           = A1
| legal_BR_comment   = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[Diário Oficial da União](/source/Di%C3%A1rio_Oficial_da_Uni%C3%A3o) |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA           = Schedule I
| legal_US           = Schedule II
| dependency_liability = High
| addiction_liability = High
| legal_UK           = Class A
| legal_DE           = Anlage I

<!--Pharmacokinetic data-->| elimination_half-life = 3-6 hours

<!--Identifiers-->| 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              = 146176
| ChEMBL_Ref         = {{ebicite|changed|EBI}}
| ChEMBL             = 1908323
| KEGG_Ref           = {{keggcite|correct|kegg}}
| KEGG               = D12696

<!--Chemical data-->| C                  = 18
| H                  = 25
| N                  = 1
| O                  = 1
| 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 (LVM)''' ([INN](/source/International_Nonproprietary_Name), [BAN](/source/British_Approved_Name)) is an [opioid](/source/opioid) [analgesic](/source/analgesic) of the [morphinan](/source/morphinan) family that has never been marketed.<ref name="Elks2014">{{cite book| vauthors = Elks J |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=Springe |isbn=978-1-4757-2085-3 |pages=656– }}</ref> It is the <small>L</small>-[stereoisomer](/source/stereoisomer) of [racemethorphan](/source/racemethorphan) (methorphan).<ref name="Elks2014" /> The effects of the two [isomer](/source/isomer)s of racemethorphan are quite different, with [dextromethorphan](/source/dextromethorphan) (DXM) being an [antitussive](/source/antitussive) at low doses and a disassociative at much higher doses.<ref name="Hornback2005">{{cite book| vauthors = Hornback JM |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–}}</ref> Levomethorphan is about five times stronger than morphine.<ref>{{cite book | vauthors = Wainer IW | chapter = Toxicology Through a Looking Glass: Stereochemical Questions and Some Answers | chapter-url = https://books.google.com/books?id=3qjUKyL7BokC&pg=PA21 | veditors = Wong SH, Sunshine I | publisher = CRC Press | date = 1996 | title = Handbook of Analytical Therapeutic Drug Monitoring and Toxicology | isbn = 9780849326486 }}</ref>

Levomethorphan is a [prodrug](/source/prodrug) to [levorphanol](/source/levorphanol), analogously to DXM acting as a prodrug to [dextrorphan](/source/dextrorphan) or [codeine](/source/codeine) behaving as a prodrug to [morphine](/source/morphine).<ref name="GudinFudin2015">{{cite journal | vauthors = Gudin J, Fudin J, Nalamachu S | title = Levorphanol use: past, present and future | journal = Postgraduate Medicine | volume = 128 | issue = 1 | pages = 46–53 | date = January 2016 | pmid = 26635068 | doi = 10.1080/00325481.2016.1128308 | s2cid = 3912175 }}</ref> As such, levomethorphan has similar effects to levorphanol but is less potent as it must be demethylated to the active form by [liver](/source/liver) [enzyme](/source/enzyme)s before being able to produce its effects.<ref name="GudinFudin2015" /> As a prodrug of levorphanol, levomethorphan functions as a potent [agonist](/source/agonist) of all three of the [opioid receptor](/source/opioid_receptor)s, [μ](/source/%CE%BC-opioid_receptor), [κ](/source/%CE%BA-opioid_receptor) (κ<sub>1</sub> and κ<sub>3</sub> but notably not κ<sub>2</sub>), and [δ](/source/%CE%B4-opioid_receptor), as an [NMDA receptor antagonist](/source/NMDA_receptor_antagonist), and as a [serotonin-norepinephrine reuptake inhibitor](/source/serotonin-norepinephrine_reuptake_inhibitor).<ref name="GudinFudin2015" /> Via activation of the κ-opioid receptor, levomethorphan can produce [dysphoria](/source/dysphoria) and [psychotomimetic](/source/psychotomimetic) effects such as [dissociation](/source/dissociation_(psychology)) and [hallucination](/source/hallucination)s.<ref name="BrueraPortenoy2009">{{cite book| vauthors = Bruera ED, Portenoy RK |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–}}</ref>

Levomethorphan is listed under the Single Convention on Narcotic Drugs 1961 and is regulated like [morphine](/source/morphine) in most countries. In the United States it is a Schedule II Narcotic controlled substance with a DEA ACSCN of 9210 and a 2014 annual aggregate manufacturing quota of 195&nbsp;grams, up from 6&nbsp;grams the year before. The salts in use are the tartrate (free base conversion ratio 0.644) and hydrobromide (0.958).<ref>{{Cite web | url = http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html | title = Conversion Factors for Controlled Substances | work = DEA Diversion Control Division | publisher = U.S. Department of Justice, Drug Enforcement Administration (DEA) | access-date = 2014-06-18 | archive-date = 2016-03-02 | archive-url = https://web.archive.org/web/20160302162948/http://deadiversion.usdoj.gov/quotas/conv_factor/index.html | url-status = dead }}</ref> As of February 2026{{when|date=February 2026}}, no levomethorphan pharmaceuticals are marketed in the United States.{{cn|date=February 2026}}

== See also ==
* [Butorphanol](/source/Butorphanol)
* [Cyclorphan](/source/Cyclorphan)
* [Levallorphan](/source/Levallorphan)
* [Levorphanol](/source/Levorphanol)
* [Nalbuphine](/source/Nalbuphine)
* [Oxilorphan](/source/Oxilorphan)
* [Proxorphan](/source/Proxorphan)
* [Racemorphan](/source/Racemorphan)
* [Xorphanol](/source/Xorphanol)

== References ==
{{Reflist}}

{{Analgesics}}
{{Hallucinogens}}
{{Navboxes
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Category:Delta-opioid receptor agonists
Category:Enantiopure drugs
Category:GABA receptor antagonists
Category:Glycine receptor antagonists
Category:Hallucinogenic kappa-opioid receptor agonists
Category:NMDA receptor antagonists
Category:Morphinans
Category:Mu-opioid receptor agonists
Category:Nociceptin receptor agonists
Category:Phenol ethers
Category:Prodrugs
Category:Semisynthetic opioids
Category:Serotonin–norepinephrine reuptake inhibitors

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Adapted from the Wikipedia article [Levomethorphan](https://en.wikipedia.org/wiki/Levomethorphan) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Levomethorphan?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.