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Details

Stereochemistry RACEMIC
Molecular Formula 2C17H23NO.2BrH.H2O
Molecular Weight 694.58
Optical Activity ( + / - )
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACEMORPHAN HYDROBROMIDE HEMIHYDRATE

SMILES

O.Br.Br.[H][C@@]12CC3=C(C=C(O)C=C3)[C@]4(CCCC[C@@]14[H])CCN2C.[H][C@@]56CC7=C(C=C(O)C=C7)[C@]8(CCCC[C@@]58[H])CCN6C

InChI

InChIKey=YJHAKXBQBWSVOL-BYVCFMHPSA-N
InChI=1S/2C17H23NO.2BrH.H2O/c2*1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17;;;/h2*5-6,11,14,16,19H,2-4,7-10H2,1H3;2*1H;1H2/t2*14-,16+,17+;;;/m00.../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
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
Interface for coupling nonaqueous wide-bore capillary electrophoresis with mass spectrometry.
2002 Feb
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.
2003 Aug
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 Dec
The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity.
2003 Jan 2
Discrimination of a single dose of morphine followed by naltrexone: substitution of other agonists for morphine and other antagonists for naltrexone in a rat model of acute dependence.
2003 Mar
Opioids and chronic neuropathic pain.
2003 Mar 27
Oral opioid therapy for chronic peripheral and central neuropathic pain.
2003 Mar 27
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor.
2003 May
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey.
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
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 Jan 1
Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis.
2004 May
[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
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
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
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
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
A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients.
2009 Jun 30
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 Sat Dec 16 10:15:09 GMT 2023
Edited
by admin
on Sat Dec 16 10:15:09 GMT 2023
Record UNII
V6H50N056L
Record Status Validated (UNII)
Record Version
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Name Type Language
RACEMORPHAN HYDROBROMIDE HEMIHYDRATE
Common Name English
MORPHINAN-3-OL, 17-METHYL-, HYDROBROMIDE, HYDRATE (2:1), (±)-
Systematic Name English
MORPHINAN-3-OL, 17-METHYL-, HYDROBROMIDE, HEMIHYDRATE, (±)-
Common Name English
DL-3-HYDROXY-N-METHYLMORPHINAN HYDROBROMIDE HEMIHYDRATE
Common Name English
Code System Code Type Description
CAS
5964-68-1
Created by admin on Sat Dec 16 10:15:09 GMT 2023 , Edited by admin on Sat Dec 16 10:15:09 GMT 2023
PRIMARY
PUBCHEM
121493154
Created by admin on Sat Dec 16 10:15:09 GMT 2023 , Edited by admin on Sat Dec 16 10:15:09 GMT 2023
PRIMARY
FDA UNII
V6H50N056L
Created by admin on Sat Dec 16 10:15:09 GMT 2023 , Edited by admin on Sat Dec 16 10:15:09 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE