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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H25NO
Molecular Weight 283.4079
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVALLORPHAN

SMILES

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

InChI

InChIKey=OZYUPQUCAUTOBP-QXAKKESOSA-N
InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H25NO
Molecular Weight 283.4079
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Levallorphan (brand name Lorfan), is an opiate antagonist of morphine family. Levallorphan was formerly used in general anesthesia, mainly to reverse the respiratory depression produced by opioid analgesics and barbiturates used for induction of surgical anaesthesia whilst maintaining a degree of analgesia. Levallorphan was also used in combination with opioid analgesics to reduce their side effects, mainly in obstetrics. The combination of levallorphan with pethidine was used so frequently, a standardized formulation was made available, known as Pethilorfan, by Roche Products Ltd in later 1950s. Is known to be used for narcotic overdose. Levallorphan is similar to naloxone but differs from naloxone in that it also possesses some agonist properties. It acts as an antagonist and partial agonist of the mu opioid receptor (MOR). Levallorphan can produce severe mental reactions at sufficient doses including hallucinations, dissociation, and other psychotomimetic effects, dysphoria, anxiety, confusion, dizziness, disorientation, derealization, feelings of drunkenness, and bizarre, unusual, or disturbing dreams.

Approval Year

Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 0.65 uM]
yes [IC50 >50 uM]
Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Effects of Innovar and innovar plus nitrous oxide on muscle tone and "H" reflex.
1971 Sep-Oct
Mechanism of morphine-induced miosis in the dog.
1975 Feb
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.
1995 Sep
Evidence for a peripheral mechanism in cardiac opioid withdrawal.
2001 Sep
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
Effects of opioids in morphine-treated pigeons trained to discriminate among morphine, the low-efficacy agonist nalbuphine, and saline.
2004 Jul
Sigma-2 receptors are specifically localized to lipid rafts in rat liver membranes.
2004 Jun 16
Determination of dextromethorphan and its metabolite dextrorphan in human urine using high performance liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry: a study of selectivity of a tandem mass spectrometric assay.
2005 Feb 25
Electron ionization mass spectra of ephedrines in a doping confirmatory procedure: a curious migration of the trimethylsilyl group in the N-acetyl-O-trimethylsilyl derivatives.
2007
Biofilm induced tolerance towards antimicrobial peptides.
2008 Apr 2
Development and validation of a chemical hydrolysis method for dextromethorphan and dextrophan determination in urine samples: application to the assessment of CYP2D6 activity in fibromyalgia patients.
2008 Jan 1
A validated SIM GC/MS method for the simultaneous determination of dextromethorphan and its metabolites dextrorphan, 3-methoxymorphinan and 3-hydroxymorphinan in biological matrices and its application to in vitro CYP2D6 and CYP3A4 inhibition study.
2009 Nov
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.
2010 Jan
Generation of novel radiolabeled opiates through site-selective iodination.
2011 Jul 1
Patents

Sample Use Guides

A dose of 2 mg levallorphan in combination with 100 mg pethidine repeated in an hour administered to women in labor
Route of Administration: Intramuscular
In Vitro Use Guide
Efficacy and potency of Levallorphan for stimulation of [35S]GTPγS binding to mMOR-CHO membranes was studied. Membranes were incubated incubated for 1 hr at 30° with various concentrations of levallorphan in the presence of 0.05 nm [35S]GTPγS and 10 uM GDP. EC50 of levallorphan was 2.7 nM. It was a partial agonist in these cells, producing ∼12% of the stimulation observed with DAMGO.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:59:52 GMT 2023
Edited
by admin
on Sat Dec 16 16:59:52 GMT 2023
Record UNII
353613BU4U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVALLORPHAN
HSDB   INN   MI   WHO-DD  
INN  
Official Name English
levallorphan [INN]
Common Name English
Levallorphan [WHO-DD]
Common Name English
LEVALLORPHAN [HSDB]
Common Name English
17-ALLYLMORPHINAN-3-OL
Systematic Name English
LEVALLORPHAN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C681
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
Code System Code Type Description
DRUG BANK
DB00504
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
PUBCHEM
5359371
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
CAS
152-02-3
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-799-1
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
DRUG CENTRAL
1560
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
FDA UNII
353613BU4U
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID9023205
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
SMS_ID
100000082820
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
MERCK INDEX
m6780
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C66004
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
IUPHAR
7209
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
INN
264
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
HSDB
2148
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL1254682
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
MESH
D007977
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
RXCUI
6370
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY RxNorm
EVMPD
SUB08452MIG
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
WIKIPEDIA
LEVALLORPHAN
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY