RACEMORPHAN

US Previously Marketed

First approved in 1953

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 Search

SMILES

CN1CC[C@]23CCCC[C@H]2[C@H]1CC4=CC=C(O)C=C34

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13097351

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Kappa opioid receptor 115 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068	Agonist 2752	2.3 nM [Ki]
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068	Agonist 2752	0.13 nM [Ki]
Delta opioid receptor 81 Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068	Agonist 2752	4.2 nM [Ki]
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14742749	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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 Health Status: unhealthy Age Group: 54 years Sex: F 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

AE	Dose	Population
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 Health Status: unhealthy Age Group: 54 years Sex: F 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 Health Status: unhealthy Age Group: 54 years Sex: F 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 Health Status: unhealthy Age Group: 54 years Sex: F 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 Health Status: unhealthy Age Group: 54 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13069264

Sourcing

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

PubMed

Title	Date	PubMed
Acute pain management in children.	2010-07-15	21197314
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.	2010-02	20394254
Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: ligands for mu, kappa, and delta opioid receptors.	2010-01-14	19928862
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.	2010-01	19797609
Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor.	2009-09	19719367
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.	2009-07	20532104
A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients.	2009-06-30	19566952
Somatostatin and opioid receptors do not regulate proliferation or apoptosis of the human multiple myeloma U266 cells.	2009-06-07	19500423
Effects of environmental enrichment on sensitivity to mu, kappa, and mixed-action opioids in female rats.	2008-07-05	18456292
Challenges in using opioids to treat pain in persons with substance use disorders.	2008-06	18497713
An evaluation of the genotoxicity of the antitussive drug Dextromethorphan.	2008-04	18160193
Opioid pharmacology.	2008-03	18443637
Opiates and elderly: use and side effects.	2008	18686750
Levorphanol revisited.	2007-12	18095794
Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A.	2007-10-26	17897634
Morphine reduces local cytokine expression and neutrophil infiltration after incision.	2007-10-02	17908329
Current aproach to cancer pain management: Availability and implications of different treatment options.	2007-06	18488078
Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.	2007-05-31	17488103
Can levorphanol be used like methadone for intractable refractory pain?	2007-04	17472497
High-affinity carbamate analogues of morphinan at opioid receptors.	2007-03-15	17276685
Levorphanol: the forgotten opioid.	2007-03	17039381
Cholesterol reduction by methyl-beta-cyclodextrin attenuates the delta opioid receptor-mediated signaling in neuronal cells but enhances it in non-neuronal cells.	2007-02-15	17141202
Role of atypical opiates in OCD. Experimental approach through the study of 5-HT(2A/C) receptor-mediated behavior.	2007-02	17102981
The effect of opiates on the activity of human placental aromatase/CYP19.	2007-01-15	17118343
Does purity of supplements count?	2007-01	17208063
Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output.	2006-09	16904173
Restless legs syndrome: diagnosis and review of management options.	2006-06	19412460
Opioid peptides and receptors in joint tissues: study in the rat.	2006-06	16649179
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.	2005-10	16419411
Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor.	2005-08	15778888
Analgesic therapy in postherpetic neuralgia: a quantitative systematic review.	2005-07	16013891
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization.	2005-07	15843500
[Fundamentals of modern treatment of myopia].	2005	16519089
Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates.	2004-09	15358985
Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis.	2004-05	14742749
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.	2004-01-01	14695830
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.	2003-12	14557376
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.	2003-11	12975489
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.	2003-08	12709780
Opioids ease neuropathic pain, but...	2003-05	12739461
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor.	2003-05	12669175
Opioids and chronic neuropathic pain.	2003-03-27	12660393
Oral opioid therapy for chronic peripheral and central neuropathic pain.	2003-03-27	12660386
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.	1995-09	7562497
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.	1991-03-01	1685312
Baclofen-induced catatonia.	1986-12	3805341
Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence.	1984-06-25	6146083
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine.	1984	6543399
Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates.	1982-01	6278540
Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys.	1981	6794076

Patents

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 `Mon Mar 31 19:27:22 GMT 2025` Edited by `admin` on `Mon Mar 31 19:27:22 GMT 2025`
Record UNII	V7R79HN3XD
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

RACEMORPHAN

Official Name

English

LEVORPHANOL DL-FORM

Preferred 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

IDS-NR-003

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C241