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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/13097351
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
Sources: https://www.drugs.com/pro/levo-dromoran.html
Curator's Comment: http://dx.doi.org/10.3109/10717549309022764
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068 |
2.3 nM [Ki] | ||
Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068 |
0.13 nM [Ki] | ||
Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635068 |
4.2 nM [Ki] | ||
Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14742749 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
---|---|---|
Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates. | 1982 Jan |
|
Age-related differences in sensitivity to the antinociceptive effects of opioids in male rats. Influence of nociceptive intensity and intrinsic efficacy at the mu receptor. | 2001 Aug |
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Central discriminative effects of morphine in rats: training via intracerebroventricular administration. | 2001 Dec |
|
The safety of dextromethorphan in pregnancy : results of a controlled study. | 2001 Feb |
|
Pitfalls of opioid rotation: substituting another opioid for methadone in patients with cancer pain. | 2002 Apr |
|
Interface for coupling nonaqueous wide-bore capillary electrophoresis with mass spectrometry. | 2002 Feb |
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Clinical pharmacology of opioids for pain. | 2002 Jul-Aug |
|
Antidepressant-like effects of tramadol and other central analgesics with activity on monoamines reuptake, in helpless rats. | 2002 Nov 29 |
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Sex-related differences in mechanical nociception and antinociception produced by mu- and kappa-opioid receptor agonists in rats. | 2002 Oct 4 |
|
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 |
|
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 |
|
Discrimination of a single dose of morphine followed by naltrexone: substitution of other agonists for morphine and other antagonists for naltrexone in a rat model of acute dependence. | 2003 Mar |
|
Opioids and chronic neuropathic pain. | 2003 Mar 27 |
|
Oral opioid therapy for chronic peripheral and central neuropathic pain. | 2003 Mar 27 |
|
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 |
|
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey. | 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 |
|
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 |
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Can levorphanol be used like methadone for intractable refractory pain? | 2007 Apr |
|
Levorphanol revisited. | 2007 Dec |
|
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 |
|
Current aproach to cancer pain management: Availability and implications of different treatment options. | 2007 Jun |
|
High-affinity carbamate analogues of morphinan at opioid receptors. | 2007 Mar 15 |
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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 |
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Challenges in using opioids to treat pain in persons with substance use disorders. | 2008 Jun |
|
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy. | 2009 Jul |
|
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy. | 2010 Feb |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/levo-dromoran.html
The usual recommended starting dose of Levorphanol for oral administration is 2 mg.
Route of Administration:
Oral
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C241
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admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
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DEA NO. |
9733
Created by
admin on Fri Dec 15 18:56:55 GMT 2023 , Edited by admin on Fri Dec 15 18:56:55 GMT 2023
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5359272
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297-90-5
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C152138
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DTXSID301016136
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100000080288
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V7R79HN3XD
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SUB10236MIG
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CHEMBL20803
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206-048-0
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Racemorphan
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m6794
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28
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ACTIVE MOIETY
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