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

Details

Stereochemistry RACEMIC
Molecular Formula C17H23NO
Molecular Weight 257.3706
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACEMORPHAN

SMILES

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

InChI

InChIKey=JAQUASYNZVUNQP-USXIJHARSA-N
InChI=1S/C17H23NO/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/t14-,16+,17+/m0/s1

HIDE SMILES / InChI

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

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
Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence.
1984 Jun 25
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
Age-related differences in sensitivity to the antinociceptive effects of opioids in male rats. Influence of nociceptive intensity and intrinsic efficacy at the mu receptor.
2001 Aug
Central discriminative effects of morphine in rats: training via intracerebroventricular administration.
2001 Dec
Interface for coupling nonaqueous wide-bore capillary electrophoresis with mass spectrometry.
2002 Feb
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
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
Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates.
2004 Sep
Restless legs syndrome: diagnosis and review of management options.
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
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 Fri Dec 15 18:56:55 GMT 2023
Edited
by admin
on Fri Dec 15 18:56:55 GMT 2023
Record UNII
V7R79HN3XD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RACEMORPHAN
INN  
INN  
Official Name English
ANTALGIN
Brand Name English
NU 2206
Code English
RACEMIC DROMORAN
Brand Name English
(±)-N-METHYLMORPHINAN-3-OL
Systematic Name English
LEVORPHANOL DL-FORM [MI]
Common Name English
NU-2206
Code English
(±)-3-HYDROXY-N-METHYLMORPHINAN
Systematic Name English
METHORPHINAN
Common Name English
(±)-N-METHYL-3-HYDROXYMORPHINAN
Systematic Name English
ORPHAN
Brand Name English
DROMORAN
Brand Name English
racemorphan [INN]
Common Name English
DL-3-HYDROXY-N-METHYLMORPHINAN
Common Name English
CETARIN
Brand Name English
MORPHINAN-3-OL, 17-METHYL-, (±)-
Systematic Name English
LEVORPHANOL DL-FORM
MI  
Common Name English
IDS-NR-003
Code English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
DEA NO. 9733
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
Code System Code Type Description
PUBCHEM
5359272
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
CAS
297-90-5
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
NCI_THESAURUS
C152138
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID301016136
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
SMS_ID
100000080288
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
FDA UNII
V7R79HN3XD
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
EVMPD
SUB10236MIG
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
ChEMBL
CHEMBL20803
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-048-0
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
WIKIPEDIA
Racemorphan
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
MERCK INDEX
m6794
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY Merck Index
INN
28
Created by admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
PRIMARY
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