Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C17H23NO.BrH |
| Molecular Weight | 338.283 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.[H][C@@]12CC3=C(C=C(O)C=C3)[C@]4(CCCC[C@@]14[H])CCN2C
InChI
InChIKey=WVFGKGPFQSEWON-DYWKTHLTSA-N
InChI=1S/C17H23NO.BrH/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
| 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 |
| Molecular Formula | BrH |
| Molecular Weight | 80.912 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Approval Year
Cmax
| 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 |
T1/2
| 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 |
Funbound
| 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: |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
Other AEs: Respiratory rate decreased, Respiratory rhythm disorder... Other AEs: Respiratory rate decreased Sources: Respiratory rhythm disorder Corneal reflex decreased Fixed dilated pupils |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Corneal reflex decreased | 5 mg multiple, subcutaneous Dose: 5 mg Route: subcutaneous Route: multiple Dose: 5 mg Sources: |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
|
| Fixed dilated pupils | 5 mg multiple, subcutaneous Dose: 5 mg Route: subcutaneous Route: multiple Dose: 5 mg Sources: |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
|
| Respiratory rate decreased | 5 mg multiple, subcutaneous Dose: 5 mg Route: subcutaneous Route: multiple Dose: 5 mg Sources: |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
|
| Respiratory rhythm disorder | 5 mg multiple, subcutaneous Dose: 5 mg Route: subcutaneous Route: multiple Dose: 5 mg Sources: |
unhealthy, 54 years n = 1 Health Status: unhealthy Age Group: 54 years Sex: F Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys. | 1981 |
|
| Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates. | 1982 Jan |
|
| Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine. | 1984 |
|
| Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence. | 1984 Jun 25 |
|
| Baclofen-induced catatonia. | 1986 Dec |
|
| Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist. | 1991 Mar-Apr |
|
| Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. | 1995 Sep |
|
| Interface for coupling nonaqueous wide-bore capillary electrophoresis with mass spectrometry. | 2002 Feb |
|
| Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence. | 2003 Aug |
|
| 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 |
|
| Opioids ease neuropathic pain, but.. | 2003 May |
|
| Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor. | 2003 May |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis. | 2004 May |
|
| Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates. | 2004 Sep |
|
| [Fundamentals of modern treatment of myopia]. | 2005 |
|
| Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor. | 2005 Aug |
|
| Analgesic therapy in postherpetic neuralgia: a quantitative systematic review. | 2005 Jul |
|
| Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization. | 2005 Jul |
|
| Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death. | 2005 Oct |
|
| Restless legs syndrome: diagnosis and review of management options. | 2006 Jun |
|
| Opioid peptides and receptors in joint tissues: study in the rat. | 2006 Jun |
|
| Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output. | 2006 Sep |
|
| Can levorphanol be used like methadone for intractable refractory pain? | 2007 Apr |
|
| Levorphanol revisited. | 2007 Dec |
|
| Role of atypical opiates in OCD. Experimental approach through the study of 5-HT(2A/C) receptor-mediated behavior. | 2007 Feb |
|
| 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 |
|
| Does purity of supplements count? | 2007 Jan |
|
| The effect of opiates on the activity of human placental aromatase/CYP19. | 2007 Jan 15 |
|
| Current aproach to cancer pain management: Availability and implications of different treatment options. | 2007 Jun |
|
| Levorphanol: the forgotten opioid. | 2007 Mar |
|
| High-affinity carbamate analogues of morphinan at opioid receptors. | 2007 Mar 15 |
|
| Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol. | 2007 May 31 |
|
| Morphine reduces local cytokine expression and neutrophil infiltration after incision. | 2007 Oct 2 |
|
| Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A. | 2007 Oct 26 |
|
| Opiates and elderly: use and side effects. | 2008 |
|
| An evaluation of the genotoxicity of the antitussive drug Dextromethorphan. | 2008 Apr |
|
| Effects of environmental enrichment on sensitivity to mu, kappa, and mixed-action opioids in female rats. | 2008 Jul 5 |
|
| Challenges in using opioids to treat pain in persons with substance use disorders. | 2008 Jun |
|
| Opioid pharmacology. | 2008 Mar |
|
| Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy. | 2009 Jul |
|
| A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients. | 2009 Jun 30 |
|
| Somatostatin and opioid receptors do not regulate proliferation or apoptosis of the human multiple myeloma U266 cells. | 2009 Jun 7 |
|
| Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor. | 2009 Sep |
|
| Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy. | 2010 Feb |
|
| Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan. | 2010 Jan |
|
| Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: ligands for mu, kappa, and delta opioid receptors. | 2010 Jan 14 |
|
| Acute pain management in children. | 2010 Jul 15 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:29:00 GMT 2023
by
admin
on
Sat Dec 16 17:29:00 GMT 2023
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| Record UNII |
5URK043N48
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| Record Status |
Validated (UNII)
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| Record Version |
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5URK043N48
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5464026
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5985-35-3
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m6794
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117861
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |