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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
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
Baclofen-induced catatonia.
1986 Dec
Clinical pharmacology of opioids for pain.
2002 Jul-Aug
The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity.
2003 Jan 2
Oral opioid therapy for chronic peripheral and central neuropathic pain.
2003 Mar 27
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey.
2003 May
Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis.
2004 May
Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor.
2005 Aug
Restless legs syndrome: diagnosis and review of management options.
2006 Jun
Opioid peptides and receptors in joint tissues: study in the rat.
2006 Jun
Levorphanol revisited.
2007 Dec
The effect of opiates on the activity of human placental aromatase/CYP19.
2007 Jan 15
Opioid pharmacology.
2008 Mar
A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients.
2009 Jun 30
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.
2010 Jan
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
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 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
DEA NO. 9733
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
Code System Code Type Description
PUBCHEM
5359272
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY
CAS
297-90-5
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY
NCI_THESAURUS
C152138
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID301016136
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY
SMS_ID
100000080288
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY
FDA UNII
V7R79HN3XD
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY
EVMPD
SUB10236MIG
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY
ChEMBL
CHEMBL20803
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-048-0
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY
WIKIPEDIA
Racemorphan
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY
MERCK INDEX
m6794
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY Merck Index
INN
28
Created by admin on Fri Dec 15 18:56:55 UTC 2023 , Edited by admin on Fri Dec 15 18:56:55 UTC 2023
PRIMARY