RACEMORPHAN HYDROCHLORIDE

US Previously Marketed

First approved in 1953

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H23NO.ClH
Molecular Weight	293.832
Optical Activity	( + / - )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[H][C@@]12CC3=C(C=C(O)C=C3)[C@]4(CCCC[C@@]14[H])CCN2C

InChI

InChIKey=MKMAMQPDRUXVSS-DYWKTHLTSA-N

InChI=1S/C17H23NO.ClH/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;1H/t14-,16+,17+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C17H23NO
Molecular Weight	257.3706
Charge	0
Count

Stereochemistry	RACEMIC
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
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine.	1984	6543399
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
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
Opioids ease neuropathic pain, but..	2003 May	12739461
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey.	2003 May	12644889
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
[Fundamentals of modern treatment of myopia].	2005	16519089
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
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
Levorphanol revisited.	2007 Dec	18095794
Does purity of supplements count?	2007 Jan	17208063
Morphine reduces local cytokine expression and neutrophil infiltration after incision.	2007 Oct 2	17908329
Challenges in using opioids to treat pain in persons with substance use disorders.	2008 Jun	18497713
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

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 `Sat Dec 16 10:15:09 UTC 2023` Edited by `admin` on `Sat Dec 16 10:15:09 UTC 2023`
Record UNII	47SM98QQ3P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RACEMORPHAN HYDROCHLORIDE

Common Name

English

MORPHINAN, 3-HYDROXY-N-METHYL-, HYDROCHLORIDE

Systematic Name

English

MORPHINAN, 3-HYDROXY-N-METHYL-, HYDROCHLORIDE, (±)-

Systematic Name

English

DL-3-HYDROXY-N-METHYLMORPHINAN HYDROCHLORIDE

Common Name

English

Code System Code Type Description

FDA UNII

47SM98QQ3P

Created by admin on Sat Dec 16 10:15:10 UTC 2023 , Edited by admin on Sat Dec 16 10:15:10 UTC 2023

PRIMARY

PUBCHEM

53324694

Created by admin on Sat Dec 16 10:15:10 UTC 2023 , Edited by admin on Sat Dec 16 10:15:10 UTC 2023

PRIMARY

CAS

6424-21-1

Created by admin on Sat Dec 16 10:15:10 UTC 2023 , Edited by admin on Sat Dec 16 10:15:10 UTC 2023

PRIMARY

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RACEMORPHAN

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					V7R79HN3XD

RACEMORPHAN

ACTIVE MOIETY

Details

SMILES

InChI

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

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2

F_unbound