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
SMILES
Cl.CN1CC[C@]23CCCC[C@H]2[C@H]1CC4=CC=C(O)C=C34
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
| 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 | ClH |
| Molecular Weight | 36.461 |
| 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 |
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 |
|
| Fixed dilated pupils | 5 mg multiple, subcutaneous Dose: 5 mg Route: subcutaneous Route: multiple Dose: 5 mg Sources: |
unhealthy, 54 years |
|
| Respiratory rate decreased | 5 mg multiple, subcutaneous Dose: 5 mg Route: subcutaneous Route: multiple Dose: 5 mg Sources: |
unhealthy, 54 years |
|
| Respiratory rhythm disorder | 5 mg multiple, subcutaneous Dose: 5 mg Route: subcutaneous Route: multiple Dose: 5 mg Sources: |
unhealthy, 54 years |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Acute pain management in children. | 2010-07-15 |
|
| Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy. | 2010-02 |
|
| Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: ligands for mu, kappa, and delta opioid receptors. | 2010-01-14 |
|
| Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan. | 2010-01 |
|
| Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor. | 2009-09 |
|
| Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy. | 2009-07 |
|
| A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients. | 2009-06-30 |
|
| Somatostatin and opioid receptors do not regulate proliferation or apoptosis of the human multiple myeloma U266 cells. | 2009-06-07 |
|
| Effects of environmental enrichment on sensitivity to mu, kappa, and mixed-action opioids in female rats. | 2008-07-05 |
|
| Challenges in using opioids to treat pain in persons with substance use disorders. | 2008-06 |
|
| An evaluation of the genotoxicity of the antitussive drug Dextromethorphan. | 2008-04 |
|
| Opioid pharmacology. | 2008-03 |
|
| Opiates and elderly: use and side effects. | 2008 |
|
| Levorphanol revisited. | 2007-12 |
|
| Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A. | 2007-10-26 |
|
| Morphine reduces local cytokine expression and neutrophil infiltration after incision. | 2007-10-02 |
|
| Current aproach to cancer pain management: Availability and implications of different treatment options. | 2007-06 |
|
| Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol. | 2007-05-31 |
|
| Can levorphanol be used like methadone for intractable refractory pain? | 2007-04 |
|
| High-affinity carbamate analogues of morphinan at opioid receptors. | 2007-03-15 |
|
| Levorphanol: the forgotten opioid. | 2007-03 |
|
| Cholesterol reduction by methyl-beta-cyclodextrin attenuates the delta opioid receptor-mediated signaling in neuronal cells but enhances it in non-neuronal cells. | 2007-02-15 |
|
| Role of atypical opiates in OCD. Experimental approach through the study of 5-HT(2A/C) receptor-mediated behavior. | 2007-02 |
|
| The effect of opiates on the activity of human placental aromatase/CYP19. | 2007-01-15 |
|
| Does purity of supplements count? | 2007-01 |
|
| Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output. | 2006-09 |
|
| Restless legs syndrome: diagnosis and review of management options. | 2006-06 |
|
| Opioid peptides and receptors in joint tissues: study in the rat. | 2006-06 |
|
| Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death. | 2005-10 |
|
| Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor. | 2005-08 |
|
| Analgesic therapy in postherpetic neuralgia: a quantitative systematic review. | 2005-07 |
|
| Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization. | 2005-07 |
|
| [Fundamentals of modern treatment of myopia]. | 2005 |
|
| Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates. | 2004-09 |
|
| Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis. | 2004-05 |
|
| 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. | 2004-01-01 |
|
| 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. | 2003-12 |
|
| 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. | 2003-11 |
|
| Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence. | 2003-08 |
|
| Opioids ease neuropathic pain, but... | 2003-05 |
|
| Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor. | 2003-05 |
|
| Opioids and chronic neuropathic pain. | 2003-03-27 |
|
| Oral opioid therapy for chronic peripheral and central neuropathic pain. | 2003-03-27 |
|
| Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. | 1995-09 |
|
| Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist. | 1991-03-01 |
|
| Baclofen-induced catatonia. | 1986-12 |
|
| Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence. | 1984-06-25 |
|
| Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine. | 1984 |
|
| Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates. | 1982-01 |
|
| Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys. | 1981 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 23:08:20 GMT 2025
by
admin
on
Mon Mar 31 23:08:20 GMT 2025
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| Record UNII |
47SM98QQ3P
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| Record Status |
Validated (UNII)
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| Record Version |
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Common Name | English | ||
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47SM98QQ3P
Created by
admin on Mon Mar 31 23:08:20 GMT 2025 , Edited by admin on Mon Mar 31 23:08:20 GMT 2025
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6424-21-1
Created by
admin on Mon Mar 31 23:08:20 GMT 2025 , Edited by admin on Mon Mar 31 23:08:20 GMT 2025
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