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 2637	2.3 nM [Ki]
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068	Agonist 2637	0.13 nM [Ki]
Delta opioid receptor 78 Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068	Agonist 2637	4.2 nM [Ki]
Glutamate [NMDA] receptor 123 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14742749	Antagonist 2737

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2554

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
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.	1991 Mar-Apr	1685312
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.	1995 Sep	7562497
The safety of dextromethorphan in pregnancy : results of a controlled study.	2001 Feb	11171724
Pitfalls of opioid rotation: substituting another opioid for methadone in patients with cancer pain.	2002 Apr	11973005
Interface for coupling nonaqueous wide-bore capillary electrophoresis with mass spectrometry.	2002 Feb	11870745
Antidepressant-like effects of tramadol and other central analgesics with activity on monoamines reuptake, in helpless rats.	2002 Nov 29	12417248
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
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	12502358
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	12604679
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
[Fundamentals of modern treatment of myopia].	2005	16519089
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
Restless legs syndrome: diagnosis and review of management options.	2006 Jun	19412460
Opioid peptides and receptors in joint tissues: study in the rat.	2006 Jun	16649179
Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output.	2006 Sep	16904173
Can levorphanol be used like methadone for intractable refractory pain?	2007 Apr	17472497
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	17141202
Does purity of supplements count?	2007 Jan	17208063
The effect of opiates on the activity of human placental aromatase/CYP19.	2007 Jan 15	17118343
Levorphanol: the forgotten opioid.	2007 Mar	17039381
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
Challenges in using opioids to treat pain in persons with substance use disorders.	2008 Jun	18497713
A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients.	2009 Jun 30	19566952
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