RACEMORPHAN

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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	Agonist 2,678	2.3 nM [Ki]
Mu opioid receptor 221	Agonist 2,678	0.13 nM [Ki]
Delta opioid receptor 77	Agonist 2,678	4.2 nM [Ki]
Glutamate [NMDA] receptor 125	Antagonist 2,778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2,578

C_max

Value	Dose	Co-administered	Analyte	Population
236 ng/mL	50 mg/kg single, oral		PROFENAMINE plasma	Rattus norvegicus

AUC

Value	Dose	Co-administered	Analyte	Population
2685 ng × h/mL	50 mg/kg single, oral		PROFENAMINE plasma	Rattus norvegicus

T_1/2

Value	Dose	Co-administered	Analyte	Population
26.1 h	50 mg/kg single, oral		PROFENAMINE plasma	Rattus norvegicus

F_unbound

Value	Dose	Co-administered	Analyte	Population
7%	50 mg/kg single, oral		PROFENAMINE plasma	Rattus norvegicus

Doses

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Dose	Population	Adverse events
5 mg multiple, subcutaneous	unhealthy, 54 years	Other AEs: Respiratory rate decreased, Respiratory rhythm disorder...

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AEs

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AE	Dose	Population
Corneal reflex decreased	5 mg multiple, subcutaneous	unhealthy, 54 years
Fixed dilated pupils	5 mg multiple, subcutaneous	unhealthy, 54 years
Respiratory rate decreased	5 mg multiple, subcutaneous	unhealthy, 54 years
Respiratory rhythm disorder	5 mg multiple, subcutaneous	unhealthy, 54 years

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Baclofen-induced catatonia.	1986 Dec	3805341
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
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