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| {{drugbox
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| | IUPAC_name = 17-methylmorphinan-3-ol
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| | image = Levorphanol.png
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| | Width = 220
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| | CAS_number = 77-07-6
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| | ATC_prefix =
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| | ATC_suffix =
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| | ATC_supplemental =
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| | PubChem = 5359272
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| | DrugBank = APRD00764
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| | C=17 | H=23 | N=1 | O=1
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| | molecular_weight = 257.371 g/mol
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| | smiles = CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)O
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| | melting_point = 23
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| | bioavailability =
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| | protein_bound = 40%
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| | metabolism =
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| | elimination_half-life = 11-16 hours
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| | excretion =
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| | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| | pregnancy_US = C
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| | pregnancy_category =
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| | legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
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| | legal_UK = <!-- GSL / P / POM / CD -->
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| | legal_US = Schedule II
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| | legal_status =
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| | routes_of_administration = oral, intravenous, intramuscular, subcutaneous
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| }}
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| '''Levorphanol''' (Levo-Dromoran®) is an [[opioid]] medication used to treat severe pain. It is the laevorotary [[stereoisomer]] of the synthetic drug [[morphinan]] (Dromoran) and a pure opioid agonist, first described in Germany in 1946 as an orally active morphine-like analgesic. Morphinan is the parent drug and prototype of a large series of opioid and/or NMDA pure or mixed agonists used in medicine including [[nalbuphine]], [[butorphanol]], [[dextromethorphan]], and others. One morphinan derivative, [[cyclorphan]] was found to be highly hallucinogenic and psychotomimetic and have other untoward effects and of course was never marketed as an analgesic.
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| Levorphanol has the same properties as [[morphine]] with respect to the potential for [[habituation]], [[tolerance]], [[physical dependence]] and [[withdrawal]] syndrome. 30 mg of oral morphine is roughly equianalgesic to 4 mg of oral levorphanol.<ref>[http://www.globalrph.com/narcoticonv.htm www.globalrph.com/narcoticonv.htm]</ref> The laevo isomer is the source of the narcotic properties of the racaemic drug Dromoran, but the dextro isomers are also useful in medicine: in addition to acting on sigma opioid receptors, the O-methyl derivative of its dextrorotary isomer, [[dextromethorphan]], acts as an [[NMDA receptor]] antagonist.<ref> Brookoff D. ''Hospital Practice''. 2000;35:45-59.</ref> Typical doses of levorphanol include 2 mg by mouth or [[subcutaneous]] injection every 6 to 8 hours.
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| Levorphanol has affinity to μ, κ, and δ [[opioid receptor]]s, but lacks complete [[cross-tolerance]] with [[morphine]]. It has a mean duration of action from 4-7 hours and for this reason is useful in palliation of chronic pain and similar conditions. Levorphanol has an oral to parenteral effectiveness ratio of 2:1, one of the most favourable of the strong narcotics. Its NMDA actions, similar to those of the phenylheptylamine open-chain narcotics such as [[methadone]] and [[ketobemidone]], make levorphanol useful for types of pain that other analgesics may not be as effective against.
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| It is chemically related to dextromethorphan, an [[antitussive]] which is not an [[analgesic]]. Dextromethorphan is a [[salt]] of the [[methyl ether]] dextrorotatory isomer of levorphanol.
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| ==Notes==
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| {{reflist|2}}
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| {{Opioids}}
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| {{pharma-stub}}
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| [[sv:Levorfanol]]
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| [[Category:Opioids]]
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| [[Category:Morphinans]]
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| [[Category:Drugs]]
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