U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO
Molecular Weight 257.3706
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVORPHANOL

SMILES

[H][C@@]12CCCC[C@@]13CCN(C)[C@@H]2CC4=C3C=C(O)C=C4

InChI

InChIKey=JAQUASYNZVUNQP-USXIJHARSA-N
InChI=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+/m0/s1

HIDE SMILES / InChI
Levorphanol, brand name Levo-Dromoran, is an opioid medication used to treat moderate to severe pain. Levorphanol is indicated for the management of moderate to severe pain where an opioid analgesic is appropriate. It is a potent synthetic opioid mu-receptor agonist similar in action to morphine. Like other opioid mu-receptor agonists, it is believed to act at receptors in both the brain and spinal cord to alter the transmission and perception of pain. The onset and peak analgesic effects following administration of levorphanol are similar to morphine when administered at equal analgesic doses. Levorphanol produces a degree of respiratory depression similar to that produced by morphine at equal analgesic doses, and like many opioid mu-receptor agonists, levorphanol produces euphoria or has a positive effect on mood in many individuals.

Originator

Curator's Comment: Levorphanol was initially synthesized in Germany in 1946

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Levorphanol Tartrate

Approved Use

Levorphanol Tartrate Tablets are indicated for the management of pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate.

Launch Date

1953
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 11.5 uM]
yes [IC50 >50 uM]
Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys.
1981
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine.
1984
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.
1991 Mar-Apr
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.
1995 Sep
Central discriminative effects of morphine in rats: training via intracerebroventricular administration.
2001 Dec
Pitfalls of opioid rotation: substituting another opioid for methadone in patients with cancer pain.
2002 Apr
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.
2003 Aug
Opioids and chronic neuropathic pain.
2003 Mar 27
Oral opioid therapy for chronic peripheral and central neuropathic pain.
2003 Mar 27
Opioids ease neuropathic pain, but..
2003 May
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor.
2003 May
Differential regulation of the human kappa opioid receptor by agonists: etorphine and levorphanol reduced dynorphin A- and U50,488H-induced internalization and phosphorylation.
2003 May
Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates.
2004 Sep
Analgesic therapy in postherpetic neuralgia: a quantitative systematic review.
2005 Jul
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization.
2005 Jul
Levorphanol revisited.
2007 Dec
Role of atypical opiates in OCD. Experimental approach through the study of 5-HT(2A/C) receptor-mediated behavior.
2007 Feb
Cholesterol reduction by methyl-beta-cyclodextrin attenuates the delta opioid receptor-mediated signaling in neuronal cells but enhances it in non-neuronal cells.
2007 Feb 15
Does purity of supplements count?
2007 Jan
The effect of opiates on the activity of human placental aromatase/CYP19.
2007 Jan 15
Levorphanol: the forgotten opioid.
2007 Mar
Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.
2007 May 31
Morphine reduces local cytokine expression and neutrophil infiltration after incision.
2007 Oct 2
Opiates and elderly: use and side effects.
2008
An evaluation of the genotoxicity of the antitussive drug Dextromethorphan.
2008 Apr
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.
2009 Jul
Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor.
2009 Sep
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.
2010 Feb
Patents

Sample Use Guides

Usual Adult Dose for Light Sedation Premedication for Anesthesia: 1 to 2 mg IM or subcutaneously, administered 60 to 90 minutes before surgery. Older or debilitated patients usually require less drug. Two mg of levorphanol is approximately equivalent to 10 to 15 mg of morphine or 100 mg of meperidine. Usual Adult Dose for Pain IV: 1 mg every 3 to 6 hours as needed. IM or subcutaneous: 1 to 2 mg every 6 to 8 hours as needed. Oral: 2 mg every 6 to 8 hours as needed. May be increased to 3 mg every 6 to 8 hours.
Route of Administration: Other
In Vitro Use Guide
Levorphanol (5-100 uM), consistently depressed the responses evoked by the putative inhibitory amino acid neurotransmitters glycine and beta-alanine but not GABA in cultured mouse spinal cord neurons.
Name Type Language
LEVORPHANOL
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
Levorphanol [WHO-DD]
Common Name English
LEVORPHANOL [HSDB]
Common Name English
LEVORPHANOL [MI]
Common Name English
RO 1-5431
Code English
levorphanol [INN]
Common Name English
IDS-NL-007
Code English
LEVORPHANOL [VANDF]
Common Name English
LEVORPHAN
Common Name English
17-METHYLMORPHINAN-3-OL
Systematic Name English
2H-10,4A-IMINOETHANOPHENANTHREN-6-OL, 1,3,4,9,10,10A-HEXAHYDRO-11-METHYL-
Systematic Name English
(-)-3-HYDROXY-N-METHYLMORPHINAN
Systematic Name English
N-METHYL-3-HYDROXYMORPHINAN
Systematic Name English
AROMARONE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
DEA NO. 9220
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
NDF-RT N0000175684
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
LIVERTOX NBK547967
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
NDF-RT N0000175690
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
NCI_THESAURUS C1506
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
Code System Code Type Description
CAS
77-07-6
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
HSDB
3349
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PRIMARY
RXCUI
6378
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PRIMARY RxNorm
ChEMBL
CHEMBL592
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PRIMARY
DAILYMED
27618J1N2X
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PRIMARY
WIKIPEDIA
LEVORPHANOL
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PRIMARY
FDA UNII
27618J1N2X
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PRIMARY
INN
91
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PRIMARY
NCI_THESAURUS
C61810
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PRIMARY
DRUG CENTRAL
1574
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PRIMARY
DRUG BANK
DB00854
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PRIMARY
EPA CompTox
DTXSID3023213
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PRIMARY
PUBCHEM
5359272
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PRIMARY
MERCK INDEX
m6794
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY Merck Index
SMS_ID
100000082303
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PRIMARY
IUPHAR
7595
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PRIMARY
MESH
D007981
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PRIMARY
EVMPD
SUB08490MIG
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-002-6
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY