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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H25NO.C4H6O6
Molecular Weight 433.4947
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVALLORPHAN TARTRATE

SMILES

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

InChI

InChIKey=FWMLYVACGDQRFU-ZTMWJVNESA-N
InChI=1S/C19H25NO.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h2,6-7,13,16,18,21H,1,3-5,8-12H2;1-2,5-6H,(H,7,8)(H,9,10)/t16-,18+,19+;1-,2-/m01/s1

HIDE SMILES / InChI

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.12 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Lorfan
Secondary
Lorfan

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
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.