LEVORPHANOL TARTRATE

First approved in 1953

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H23NO.C4H6O6.2H2O
Molecular Weight	443.488
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=UMZNDVASJKIQCB-QLFXFZCRSA-N

InChI=1S/C17H23NO.C4H6O6.2H2O/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17;5-1(3(7)8)2(6)4(9)10;;/h5-6,11,14,16,19H,2-4,7-10H2,1H3;1-2,5-6H,(H,7,8)(H,9,10);2*1H2/t14-,16+,17+;1-,2-;;/m01../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	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

Description
Sources: https://www.drugs.com/pro/levorphanol.html | https://www.ncbi.nlm.nih.gov/pubmed/17039381

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17039381 \| https://www.ncbi.nlm.nih.gov/pubmed/17276685	Agonist 2752	0.21 nM [Ki]
Delta opioid receptor 81 Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17039381	Agonist 2752	4.2 nM [Ki]
Kappa opioid receptor 115 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17039381	Agonist 2752	2.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/074278.PDF	Palliative		Approved 8583	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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252		substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes [IC50 11.5 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes [IC50 >50 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes

Sourcing

Vendor/Aggregator	ID	URL
AAA Chemistry	AR-1E1926
ABI Chem	AC1L1H05
ABI Chem	AC1Q7AI1
AHH Chemical co.,ltd	MT-53063	http://www.ahhchemical.com/product/MT-53063.html
BioChemPartner	BCP24334	http://www.biochempartner.com/125-73-5-BCP24334
BOC Sciences	125-73-5	https://www.bocsci.com/dextromethorphan-ep-impurity-b-dextrorphan-cas-125-73-5-item-470048.html
Clearsynth	CS-O-16970	https://www.clearsynth.com/en/CSO16970.html
Compound Cloud	5359272
Compound Cloud	5462348
eMolecules	261267554
eMolecules	48858227
HongKong Chemhere	SCA54099
MuseChem	I014442
NovoSeek	3918
NovoSeek	5390113
Smolecule	S532999	http://www.smolecule.com/products/s532999
Tetrahedron	TS81326
THE BioTek	bt-272670	https://www.thebiotek.com/product/inhibitors/bt-272670
Toronto Research Chemicals	KIT8295
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0703A
ZINC	ZINC000003812984	http://zinc15.docking.org/substances/ZINC000003812984

PubMed

Title	Date	PubMed
Acute pain management in children.	2010-07-15	21197314
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.	2010-02	20394254
Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: ligands for mu, kappa, and delta opioid receptors.	2010-01-14	19928862
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.	2010-01	19797609
Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor.	2009-09	19719367
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.	2009-07	20532104
A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients.	2009-06-30	19566952
Somatostatin and opioid receptors do not regulate proliferation or apoptosis of the human multiple myeloma U266 cells.	2009-06-07	19500423
Effects of environmental enrichment on sensitivity to mu, kappa, and mixed-action opioids in female rats.	2008-07-05	18456292
Challenges in using opioids to treat pain in persons with substance use disorders.	2008-06	18497713
An evaluation of the genotoxicity of the antitussive drug Dextromethorphan.	2008-04	18160193
Opioid pharmacology.	2008-03	18443637
Opiates and elderly: use and side effects.	2008	18686750
Levorphanol revisited.	2007-12	18095794
Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A.	2007-10-26	17897634
Morphine reduces local cytokine expression and neutrophil infiltration after incision.	2007-10-02	17908329
Current aproach to cancer pain management: Availability and implications of different treatment options.	2007-06	18488078
Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.	2007-05-31	17488103
Can levorphanol be used like methadone for intractable refractory pain?	2007-04	17472497
High-affinity carbamate analogues of morphinan at opioid receptors.	2007-03-15	17276685
Levorphanol: the forgotten opioid.	2007-03	17039381
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	17141202
Role of atypical opiates in OCD. Experimental approach through the study of 5-HT(2A/C) receptor-mediated behavior.	2007-02	17102981
The effect of opiates on the activity of human placental aromatase/CYP19.	2007-01-15	17118343
Does purity of supplements count?	2007-01	17208063
Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output.	2006-09	16904173
Restless legs syndrome: diagnosis and review of management options.	2006-06	19412460
Opioid peptides and receptors in joint tissues: study in the rat.	2006-06	16649179
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.	2005-10	16419411
Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor.	2005-08	15778888
Analgesic therapy in postherpetic neuralgia: a quantitative systematic review.	2005-07	16013891
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization.	2005-07	15843500
[Fundamentals of modern treatment of myopia].	2005	16519089
Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates.	2004-09	15358985
Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis.	2004-05	14742749
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	14695830
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	14557376
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	12975489
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.	2003-08	12709780
Opioids ease neuropathic pain, but...	2003-05	12739461
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor.	2003-05	12669175
Opioids and chronic neuropathic pain.	2003-03-27	12660393
Oral opioid therapy for chronic peripheral and central neuropathic pain.	2003-03-27	12660386
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.	1995-09	7562497
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.	1991-03-01	1685312
Baclofen-induced catatonia.	1986-12	3805341
Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence.	1984-06-25	6146083
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine.	1984	6543399
Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates.	1982-01	6278540
Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys.	1981	6794076

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 18:01:23 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:23 GMT 2025`
Record UNII	04WQU6T9QI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVO-DROMORAN

Preferred Name

English

LEVORPHANOL TARTRATE

Common Name

English

RO-1-5431/7

Code

English

Levorphanol tartrate dihydrate [WHO-DD]

Common Name

English

17-Methylmorphinan-3-ol, tartrate (1:1) (salt) dihydrate

Common Name

English

LEVORPHANOL TARTRATE [MART.]

Common Name

English

LEVORPHANOL TARTRATE DIHYDRATE [MI]

Common Name

English

LEVORPHANOL TARTRATE [USP-RS]

Common Name

English

MORPHINAN-3-OL, 17-METHYL-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1) (SALT), DIHYDRATE

Common Name

English

LEVORPHANOL TARTRATE [USP MONOGRAPH]

Common Name

English

LEVORPHANOL TARTRATE [VANDF]

Common Name

English

LEVORPHANOL TARTRATE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1506