U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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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
Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys.
1981
Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates.
1982 Jan
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine.
1984
Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence.
1984 Jun 25
Baclofen-induced catatonia.
1986 Dec
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
Age-related differences in sensitivity to the antinociceptive effects of opioids in male rats. Influence of nociceptive intensity and intrinsic efficacy at the mu receptor.
2001 Aug
The safety of dextromethorphan in pregnancy : results of a controlled study.
2001 Feb
Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates.
2004 Sep
[Fundamentals of modern treatment of myopia].
2005
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
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.
2005 Oct
Restless legs syndrome: diagnosis and review of management options.
2006 Jun
Opioid peptides and receptors in joint tissues: study in the rat.
2006 Jun
Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output.
2006 Sep
Can levorphanol be used like methadone for intractable refractory pain?
2007 Apr
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
Current aproach to cancer pain management: Availability and implications of different treatment options.
2007 Jun
Levorphanol: the forgotten opioid.
2007 Mar
High-affinity carbamate analogues of morphinan at opioid receptors.
2007 Mar 15
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
Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A.
2007 Oct 26
Opiates and elderly: use and side effects.
2008
An evaluation of the genotoxicity of the antitussive drug Dextromethorphan.
2008 Apr
Effects of environmental enrichment on sensitivity to mu, kappa, and mixed-action opioids in female rats.
2008 Jul 5
Challenges in using opioids to treat pain in persons with substance use disorders.
2008 Jun
Opioid pharmacology.
2008 Mar
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.
2009 Jul
A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients.
2009 Jun 30
Somatostatin and opioid receptors do not regulate proliferation or apoptosis of the human multiple myeloma U266 cells.
2009 Jun 7
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
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.
2010 Jan
Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: ligands for mu, kappa, and delta opioid receptors.
2010 Jan 14
Acute pain management in children.
2010 Jul 15
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
Related Record Type Details
TARGET -> AGONIST
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TARGET -> INHIBITOR
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TARGET -> AGONIST
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SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
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BINDER->LIGAND
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TARGET -> AGONIST
Ki
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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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