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

CN1CC[C@]23CCCC[C@H]2[C@H]1CC4=CC=C(O)C=C34

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

Molecular Formula C17H23NO
Molecular Weight 257.3706
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Acute pain management in children.
2010-07-15
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.
2010-02
Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: ligands for mu, kappa, and delta opioid receptors.
2010-01-14
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.
2010-01
Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor.
2009-09
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.
2009-07
A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients.
2009-06-30
Somatostatin and opioid receptors do not regulate proliferation or apoptosis of the human multiple myeloma U266 cells.
2009-06-07
Effects of environmental enrichment on sensitivity to mu, kappa, and mixed-action opioids in female rats.
2008-07-05
Challenges in using opioids to treat pain in persons with substance use disorders.
2008-06
An evaluation of the genotoxicity of the antitussive drug Dextromethorphan.
2008-04
Opioid pharmacology.
2008-03
Opiates and elderly: use and side effects.
2008
Levorphanol revisited.
2007-12
Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A.
2007-10-26
Morphine reduces local cytokine expression and neutrophil infiltration after incision.
2007-10-02
Current aproach to cancer pain management: Availability and implications of different treatment options.
2007-06
Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.
2007-05-31
Can levorphanol be used like methadone for intractable refractory pain?
2007-04
High-affinity carbamate analogues of morphinan at opioid receptors.
2007-03-15
Levorphanol: the forgotten opioid.
2007-03
Cholesterol reduction by methyl-beta-cyclodextrin attenuates the delta opioid receptor-mediated signaling in neuronal cells but enhances it in non-neuronal cells.
2007-02-15
Role of atypical opiates in OCD. Experimental approach through the study of 5-HT(2A/C) receptor-mediated behavior.
2007-02
The effect of opiates on the activity of human placental aromatase/CYP19.
2007-01-15
Does purity of supplements count?
2007-01
Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output.
2006-09
Restless legs syndrome: diagnosis and review of management options.
2006-06
Opioid peptides and receptors in joint tissues: study in the rat.
2006-06
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.
2005-10
Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor.
2005-08
Analgesic therapy in postherpetic neuralgia: a quantitative systematic review.
2005-07
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization.
2005-07
[Fundamentals of modern treatment of myopia].
2005
Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates.
2004-09
Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis.
2004-05
10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors.
2004-01-01
Differential effects of agonists on adenylyl cyclase superactivation mediated by the kappa opioid receptors: adenylyl cyclase superactivation is independent of agonist-induced phosphorylation, desensitization, internalization, and down-regulation.
2003-12
The competitive N-methyl-D-aspartate receptor antagonist (-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid (LY235959) potentiates the antinociceptive effects of opioids that vary in efficacy at the mu-opioid receptor.
2003-11
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.
2003-08
Opioids ease neuropathic pain, but...
2003-05
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor.
2003-05
Opioids and chronic neuropathic pain.
2003-03-27
Oral opioid therapy for chronic peripheral and central neuropathic pain.
2003-03-27
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.
1995-09
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.
1991-03-01
Baclofen-induced catatonia.
1986-12
Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence.
1984-06-25
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine.
1984
Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates.
1982-01
Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys.
1981
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.
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:23:57 GMT 2025
Edited
by admin
on Wed Apr 02 09:23:57 GMT 2025
Record UNII
27618J1N2X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IDS-NL-007
Preferred Name English
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
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 Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
DEA NO. 9220
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
NDF-RT N0000175684
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
LIVERTOX NBK547967
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
NDF-RT N0000175690
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
NCI_THESAURUS C1506
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
Code System Code Type Description
CAS
77-07-6
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
HSDB
3349
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
RXCUI
6378
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL592
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
DAILYMED
27618J1N2X
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
WIKIPEDIA
LEVORPHANOL
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
FDA UNII
27618J1N2X
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
INN
91
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
NCI_THESAURUS
C61810
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
DRUG CENTRAL
1574
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
DRUG BANK
DB00854
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
EPA CompTox
DTXSID3023213
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
PUBCHEM
5359272
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
MERCK INDEX
m6794
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY Merck Index
SMS_ID
100000082303
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
IUPHAR
7595
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
MESH
D007981
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
EVMPD
SUB08490MIG
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-002-6
Created by admin on Wed Apr 02 09:23:57 GMT 2025 , Edited by admin on Wed Apr 02 09:23:57 GMT 2025
PRIMARY
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
CLEARANCE PHARMACOKINETIC
CSF/PLASMA RATIO PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC