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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
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

Description

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

CNS Penetrant
2554
Curator's Comment: http://dx.doi.org/10.3109/10717549309022764

Originator

Approval Year

1953
193
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 2.3 nM [Ki]
Agonist
2678
 0.13 nM [Ki]
Agonist
2678
 4.2 nM [Ki]
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
236 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10211869/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10211869/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10211869/
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%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10211869/
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:
https://pubmed.ncbi.nlm.nih.gov/13069264
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13069264
Other AEs: Respiratory rate decreased, Respiratory rhythm disorder...
Other AEs:
Respiratory rate decreased
Respiratory rhythm disorder
Corneal reflex decreased
Fixed dilated pupils
Sources:
https://pubmed.ncbi.nlm.nih.gov/13069264
AEs

AEs

AESignificanceDosePopulation
Corneal reflex decreased
5 mg multiple, subcutaneous
Dose: 5 mg
Route: subcutaneous
Route: multiple
Dose: 5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/13069264
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13069264
Fixed dilated pupils
5 mg multiple, subcutaneous
Dose: 5 mg
Route: subcutaneous
Route: multiple
Dose: 5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/13069264
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13069264
Respiratory rate decreased
5 mg multiple, subcutaneous
Dose: 5 mg
Route: subcutaneous
Route: multiple
Dose: 5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/13069264
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13069264
Respiratory rhythm disorder
5 mg multiple, subcutaneous
Dose: 5 mg
Route: subcutaneous
Route: multiple
Dose: 5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/13069264
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13069264
Sourcing

Sourcing

Vendor/AggregatorIDURL
AAA Chemistry
AR-1E1926
ABI Chem
AC1L1H05
ABI Chem
AC1Q7AI1
AHH Chemical co.,ltd
MT-53063
http://www.ahhchemical.com/product/MT-53063.html
BOC Sciences
125-73-5
https://www.bocsci.com/dextromethorphan-ep-impurity-b-dextrorphan-cas-125-73-5-item-470048.html
BioChemPartner
BCP24334
http://www.biochempartner.com/125-73-5-BCP24334
Clearsynth
CS-O-16970
https://www.clearsynth.com/en/CSO16970.html
Compound Cloud
5359272
Compound Cloud
5462348
HongKong Chemhere
SCA54099
MuseChem
I014442
NovoSeek
3918
NovoSeek
5390113
Smolecule
S532999
http://www.smolecule.com/products/s532999
THE BioTek
bt-272670
https://www.thebiotek.com/product/inhibitors/bt-272670
Tetrahedron
TS81326
Toronto Research Chemicals
KIT8295
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.
PH-0703A
ZINC
ZINC000003812984
http://zinc15.docking.org/substances/ZINC000003812984
eMolecules
261267554
eMolecules
48858227
PubMed

PubMed

TitleDatePubMed
Baclofen-induced catatonia.
1986 Dec
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.
1995 Sep
Antidepressant-like effects of tramadol and other central analgesics with activity on monoamines reuptake, in helpless rats.
2002 Nov 29
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
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor.
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
Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates.
2004 Sep
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
Levorphanol revisited.
2007 Dec
The effect of opiates on the activity of human placental aromatase/CYP19.
2007 Jan 15
Effects of environmental enrichment on sensitivity to mu, kappa, and mixed-action opioids in female rats.
2008 Jul 5
Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: ligands for mu, kappa, and delta opioid receptors.
2010 Jan 14
Patents

Patents

JP2000212069A
12
JP2001128695A
9
JP2002010788A
9
JP2003511351A
27
JP2005204666A
9
JP2005204667A
9
JP2005291742A
9
JP2005536450A
11
JP4737583B2
22
JPH03163030A
3

Sample Use Guides

In Vivo Use Guide
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
Related Record Type Details
Structure of RACEMORPHAN HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of RACEMORPHAN HYDROBROMIDE HEMIHYDRATE
SALT/SOLVATE -> PARENT
Structure of RACEMORPHAN HYDROBROMIDE
SALT/SOLVATE -> PARENT
Structure of RACEMORPHAN SULFATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of RACEMORPHAN
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