U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H23NO.BrH
Molecular Weight 338.283
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACEMORPHAN HYDROBROMIDE

SMILES

Br.[H][C@@]12CC3=C(C=C(O)C=C3)[C@]4(CCCC[C@@]14[H])CCN2C

InChI

InChIKey=WVFGKGPFQSEWON-DYWKTHLTSA-N
InChI=1S/C17H23NO.BrH/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;1H/t14-,16+,17+;/m0./s1

HIDE SMILES / InChI

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

Racemorphan is racemic mixture of an antitussive and dissociative hallucinogen Dextrorphan and an opioid analgesic Levorphanol. Racemorphan itself is under international control per the Single Convention on Narcotic Drugs 1961 and is therefore listed as a Schedule II Narcotic controlled substance.

CNS Activity

Curator's Comment: http://dx.doi.org/10.3109/10717549309022764

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.3 nM [Ki]
0.13 nM [Ki]
4.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
236 ng/mL
50 mg/kg single, oral
dose: 50 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROFENAMINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2685 ng × h/mL
50 mg/kg single, oral
dose: 50 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROFENAMINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
26.1 h
50 mg/kg single, oral
dose: 50 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROFENAMINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7%
50 mg/kg single, oral
dose: 50 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROFENAMINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
5 mg multiple, subcutaneous
Dose: 5 mg
Route: subcutaneous
Route: multiple
Dose: 5 mg
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
Other AEs: Respiratory rate decreased, Respiratory rhythm disorder...
Other AEs:
Respiratory rate decreased
Respiratory rhythm disorder
Corneal reflex decreased
Fixed dilated pupils
Sources:
AEs

AEs

AESignificanceDosePopulation
Corneal reflex decreased
5 mg multiple, subcutaneous
Dose: 5 mg
Route: subcutaneous
Route: multiple
Dose: 5 mg
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
Fixed dilated pupils
5 mg multiple, subcutaneous
Dose: 5 mg
Route: subcutaneous
Route: multiple
Dose: 5 mg
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
Respiratory rate decreased
5 mg multiple, subcutaneous
Dose: 5 mg
Route: subcutaneous
Route: multiple
Dose: 5 mg
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
Respiratory rhythm disorder
5 mg multiple, subcutaneous
Dose: 5 mg
Route: subcutaneous
Route: multiple
Dose: 5 mg
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
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
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.
1995 Sep
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
Opioids and chronic neuropathic pain.
2003 Mar 27
Oral opioid therapy for chronic peripheral and central neuropathic pain.
2003 Mar 27
Opioids ease neuropathic pain, but..
2003 May
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
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 Nov
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
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
Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor.
2005 Aug
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

The usual recommended starting dose of Levorphanol for oral administration is 2 mg.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:29:00 GMT 2023
Edited
by admin
on Sat Dec 16 17:29:00 GMT 2023
Record UNII
5URK043N48
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RACEMORPHAN HYDROBROMIDE
Common Name English
LEVORPHANOL DL-FORM HYDROBROMIDE
MI  
Common Name English
MORPHINAN-3-OL, 17-METHYL-, HYDROBROMIDE, (±)-
Systematic Name English
LEVORPHANOL DL-FORM HYDROBROMIDE [MI]
Common Name English
DL-3-HYDROXY-N-METHYLMORPHINAN HYDROBROMIDE
Common Name English
NSC-117861
Code English
RACEMORPHAN HBR
Common Name English
MORPHINAN-3-OL, N-METHYL-, HYDROBROMIDE, (±)-
Systematic Name English
METHORPHINAN HYDROBROMIDE
Common Name English
METHORPHINAN HBR
Common Name English
Code System Code Type Description
FDA UNII
5URK043N48
Created by admin on Sat Dec 16 17:29:00 GMT 2023 , Edited by admin on Sat Dec 16 17:29:00 GMT 2023
PRIMARY
PUBCHEM
5464026
Created by admin on Sat Dec 16 17:29:00 GMT 2023 , Edited by admin on Sat Dec 16 17:29:00 GMT 2023
PRIMARY
CAS
5985-35-3
Created by admin on Sat Dec 16 17:29:00 GMT 2023 , Edited by admin on Sat Dec 16 17:29:00 GMT 2023
PRIMARY
MERCK INDEX
m6794
Created by admin on Sat Dec 16 17:29:00 GMT 2023 , Edited by admin on Sat Dec 16 17:29:00 GMT 2023
PRIMARY Merck Index
NSC
117861
Created by admin on Sat Dec 16 17:29:00 GMT 2023 , Edited by admin on Sat Dec 16 17:29:00 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
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ACTIVE MOIETY