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

[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

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 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068	Agonist 2678	2.3 nM [Ki]
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068	Agonist 2678	0.13 nM [Ki]
Delta opioid receptor 77 Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068	Agonist 2678	4.2 nM [Ki]
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14742749	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

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 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

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 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

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
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

Title	Date	PubMed
Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys.	1981	6794076
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.	1995 Sep	7562497
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	11498722
The safety of dextromethorphan in pregnancy : results of a controlled study.	2001 Feb	11171724
Clinical pharmacology of opioids for pain.	2002 Jul-Aug	12479250
Sex-related differences in mechanical nociception and antinociception produced by mu- and kappa-opioid receptor agonists in rats.	2002 Oct 4	12354566
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.	2003 Aug	12709780
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	14557376
Opioids and chronic neuropathic pain.	2003 Mar 27	12660393
Oral opioid therapy for chronic peripheral and central neuropathic pain.	2003 Mar 27	12660386
Opioids ease neuropathic pain, but..	2003 May	12739461
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor.	2003 May	12669175
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	12975489
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	14695830
Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis.	2004 May	14742749
Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates.	2004 Sep	15358985
Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor.	2005 Aug	15778888
Analgesic therapy in postherpetic neuralgia: a quantitative systematic review.	2005 Jul	16013891
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization.	2005 Jul	15843500
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.	2005 Oct	16419411
Restless legs syndrome: diagnosis and review of management options.	2006 Jun	19412460
Can levorphanol be used like methadone for intractable refractory pain?	2007 Apr	17472497
Levorphanol revisited.	2007 Dec	18095794
Role of atypical opiates in OCD. Experimental approach through the study of 5-HT(2A/C) receptor-mediated behavior.	2007 Feb	17102981
Does purity of supplements count?	2007 Jan	17208063
The effect of opiates on the activity of human placental aromatase/CYP19.	2007 Jan 15	17118343
Current aproach to cancer pain management: Availability and implications of different treatment options.	2007 Jun	18488078
High-affinity carbamate analogues of morphinan at opioid receptors.	2007 Mar 15	17276685
Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.	2007 May 31	17488103
Morphine reduces local cytokine expression and neutrophil infiltration after incision.	2007 Oct 2	17908329
Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A.	2007 Oct 26	17897634
Opiates and elderly: use and side effects.	2008	18686750
An evaluation of the genotoxicity of the antitussive drug Dextromethorphan.	2008 Apr	18160193
Effects of environmental enrichment on sensitivity to mu, kappa, and mixed-action opioids in female rats.	2008 Jul 5	18456292
Challenges in using opioids to treat pain in persons with substance use disorders.	2008 Jun	18497713
Somatostatin and opioid receptors do not regulate proliferation or apoptosis of the human multiple myeloma U266 cells.	2009 Jun 7	19500423
Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor.	2009 Sep	19719367
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.	2010 Jan	19797609

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

Name

Type

Language

RACEMORPHAN

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

Common Name

English

IDS-NR-003

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C241