Levorphanol

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Opioid analgesic drug

title: "Levorphanol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["delta-opioid-receptor-agonists", "enantiopure-drugs", "euphoriants", "gaba-receptor-antagonists", "german-inventions", "glycine-receptor-antagonists", "hallucinogenic-kappa-opioid-receptor-agonists", "morphinans", "mu-opioid-receptor-agonists", "nmda-receptor-antagonists", "nociceptin-receptor-agonists", "hydroxyarenes", "serotonin–norepinephrine-reuptake-inhibitors", "synthetic-opioids"] description: "Opioid analgesic drug" topic_path: "geography/germany" source: "https://en.wikipedia.org/wiki/Levorphanol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Opioid analgesic drug ::

Levorphanol (brand name Levo-Dromoran) is an opioid medication used to treat moderate to severe pain. It is the levorotatory enantiomer of the compound racemorphan. Its dextrorotatory counterpart is dextrorphan.

It was first described in Germany in 1946. The drug has been in medical use in the United States since 1953.

Pharmacology

Levorphanol acts predominantly as an agonist of the μ-opioid receptor (MOR), but is also an agonist of the δ-opioid receptor (DOR), κ-opioid receptor (KOR), and the nociceptin receptor (NOP), as well as an NMDA receptor antagonist and a serotonin-norepinephrine reuptake inhibitor (SNRI). Levorphanol, similarly to certain other opioids, also acts as a glycine receptor antagonist and GABA receptor antagonist at very high concentrations. As per the World Health Organization, levorphanol is a step 3 opioid and is considered eight times more potent than morphine at the MOR (2 mg levorphanol is equivalent to 15 mg morphine).

Relative to morphine, levorphanol lacks complete cross-tolerance and possesses greater intrinsic activity at the MOR. Levorphanol's exceptionally high analgesic efficacy in the treatment of neuropathic pain is also conferred by its action on serotonin and norepinephrine transporters, similar to the opioids tramadol and tapentadol, and mutually complements the analgesic effect of its NMDA receptor antagonism.

Levorphanol shows a high rate of psychotomimetic side effects such as hallucinations and delirium, which have been attributed to its binding to and activation of the KOR. At the same time however, activation of this receptor as well as of the DOR have been determined to contribute to its analgesic effects.

Chemistry

::figure[src="https://upload.wikimedia.org/wikipedia/commons/e/e2/Levorphanol_and_dextrorphan.png" caption="Levorphanol and its stereoisomer dextrorphan, the enantiomers of the racemic mixture racemorphan."] ::

Chemically, levorphanol belongs to the morphinan class and is (−)-3-hydroxy-N-methyl-morphinan. It is the "left-handed" (levorotatory) stereoisomer of racemorphan, the racemic mixture of the two stereoisomers with differing pharmacology. The "right-handed" (dextrorotatory) enantiomer of racemorphan is dextrorphan (DXO), an antitussive, potent dissociative hallucinogen (NMDA receptor antagonist), and weakly active opioid. DXO is an active metabolite of the pharmaceutical drug dextromethorphan (DXM), which, analogously to DXO, is an enantiomer of the racemic mixture racemethorphan along with levomethorphan, the latter of which has similar properties to those of levorphanol.

Society and culture

Name

Levorphanol is the INN, BAN, and DCF. As the medically used tartrate salt, the drug is also known as levorphanol tartrate (USAN, BANM). The former developmental code name of levorphanol at Roche was Ro 1-5431.

Availability

As the tartrate salt, levorphanol is marketed by Hikma Pharmaceuticals USA Inc. and Virtus Pharmaceuticals in the U.S., and Canada under the brand name Levo-Dromoran.

Legality

Levorphanol is listed under the Single Convention On Narcotic Drugs 1961 and is regulated like morphine in most countries. In the U.S., it is a Schedule II Narcotic controlled substance with a DEA ACSCN of 9220 and 2013 annual aggregate manufacturing quota of 4.5 kilograms. The salts in use are the tartrate (free base conversion ratio 0.58) and hydrobromide (0.76).

References

Anvisa. (March 31, 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
(November 14, 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
(January 2000). "Index Nominum 2000: International Drug Directory". Taylor & Francis.
(December 6, 2012). "Concise Dictionary of Pharmacological Agents: Properties and Synonyms". Springer Science & Business Media.
(2006). "Analogue-based Drug Discovery". John Wiley & Sons.
(January 2016). "Levorphanol Use: Past, Present and Future". Postgraduate Medicine.
Osborne, Neville N.. (October 22, 2013). "Selected Topics from Neurochemistry". Elsevier Science.
(2009). "Opioids in Cancer Pain". Oxford University Press.
(March 2007). "Levorphanol: the forgotten opioid". Supportive Care in Cancer.
(April 2016). "Levorphanol, another choice in opioid rotation". J Pain.
(October 12, 2009). "Cancer Pain: Assessment and Management". Cambridge University Press.
"LEVORPHANOL TARTRATE tablet". National Institutes of Health.
"Conversion Factors for Controlled Substances". U.S. Department of Justice • Drug Enforcement Administration.

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