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

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 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
Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates.	1982 Jan	6278540
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine.	1984	6543399
Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence.	1984 Jun 25	6146083
Baclofen-induced catatonia.	1986 Dec	3805341
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.	1995 Sep	7562497
Central discriminative effects of morphine in rats: training via intracerebroventricular administration.	2001 Dec	11786240
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
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
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
Opioids and chronic neuropathic pain.	2003 Mar 27	12660393
Oral opioid therapy for chronic peripheral and central neuropathic pain.	2003 Mar 27	12660386
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor.	2003 May	12669175
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey.	2003 May	12644889
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	12606694
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
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
Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output.	2006 Sep	16904173
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
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
Morphine reduces local cytokine expression and neutrophil infiltration after incision.	2007 Oct 2	17908329
Opioid pharmacology.	2008 Mar	18443637
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.	2009 Jul	20532104
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
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.	2010 Feb	20394254
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.	2010 Jan	19797609
Acute pain management in children.	2010 Jul 15	21197314

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 `Fri Dec 15 18:56:55 UTC 2023` Edited by `admin` on `Fri Dec 15 18:56:55 UTC 2023`
Record UNII	V7R79HN3XD
Record Status	`Validated (UNII)`
Record Version

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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