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    Oxymorphone molecular structure

    Oxymorphone Stats & Data

    Opana Numorphan Stop signs stopsigns
    NPS DataHub
    MW301.34
    FormulaC17H19NO4
    CAS76-41-5
    IUPAC4,5α-epoxy-3,14-dihydroxy-17-methylmorphinan-6-one
    SMILESCN1CCC23C4C(=O)CCC3(O)C1Cc1ccc(O)c(O4)c12
    InChIKeyUQCNKQCJZOAFTQ-ISWURRPUSA-N
    Chemical Class medicine
    Psychoactive Class Depressant

    Pharmacology

    DrugBank
    Half-life 1.3 (+/-0.7) hours State Solid

    Description

    An opioid analgesic with actions and uses similar to those of morphine, apart from an absence of cough suppressant activity. It is used in the treatment of moderate to severe pain, including pain in obstetrics. It may also be used as an adjunct to anesthesia (From Martindale, The Extra Pharmacopoeia, 30th ed, p1092). On June 8, 2017, FDA requested Endo Pharmaceuticals to remove the medication from the market due to opioid misuse and abuse risks associated with the product's injectable reformulation.

    Mechanism of Action

    Oxymorphone interacts predominantly with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, with high densities in the posterior amygdala, hypothalamus, thalamus, nucleus caudatus, putamen, and certain cortical areas. They are also found on the terminal axons of primary afferents within laminae I and II (substantia gelatinosa) of the spinal cord and in the spinal nucleus of the trigeminal nerve. Also, it has been shown that oxymorphone binds to and inhibits GABA inhibitory interneurons via mu-receptors. These interneurons normally inhibit the descending pain inhibition pathway. So, without the inhibitory signals, pain modulation can proceed downstream.

    Pharmacodynamics

    Oxymorphone is a semi-synthetic opioid substitute for morphine. It is a potent analgesic. Opioid analgesics exert their principal pharmacologic effects on the CNS and the gastrointestinal tract. The principal actions of therapeutic value are analgesia and sedation. Opioids produce respiratory depression by direct action on brain stem respiratory centers. The mechanism of respiratory depression involves a reduction in the responsiveness of the brain stem respiratory centers to increases in carbon dioxide tension and to electrical stimulation.

    Metabolism

    Oxymorphone undergoes extensive hepatic metabolism in humans. After a 10 mg oral dose, 49% was excreted over a five-day period in the urine. Of this, 82% was excreted in the first 24 hours after administration. The recovered drug-related products contained the oxymorphone (1.9%), the conjugate of oxymorphone (44.1%), the 6(beta)-carbinol produced by 6-keto reduction of oxymorphone (0.3%), and the conjugates of 6(beta)-carbinol (2.6%) and 6(alpha)-carbinol (0.1%).

    Toxicity

    Oxymorphone overdosage is characterized by respiratory depression, extreme somnolence progressing to stupor or coma, skeletal muscle flaccidity, cold and clammy skin, and sometimes bradycardia and hypotension. Patients experiencing an overdose may develop apnea, circulatory collapse, and cardiac arrest. Intravenous mouse LD50 is 172 mg/kg.

    Indication

    For the treatment of moderate-to-severe pain.

    Elimination

    Oxymorphone is highly metabolized, principally in the liver, and undergoes reduction or conjugation with glucuronic acid to form both active and inactive products. Because oxymorphone is extensively metabolized, <1% of the administered dose is excreted unchanged in the urine.

    Receptor Profile

    Receptor Actions

    Agonists
    μ-opioid receptor agonist (full)
    δ-opioid receptor agonist (partial)
    κ-opioid receptor agonist (weak)

    Receptor Binding

    Mu-type opioid receptor agonist
    Delta-type opioid receptor antagonist

    History & Culture

    1914–1959

    Oxymorphone was first developed in Germany in 1914 as part of efforts to create opioid analgesics with improved side effect profiles compared to morphine and heroin. The compound exhibits actions and uses similar to morphine, though notably lacks cough suppressant activity. During the 1930s, researchers developed mono-, di-, tri-, and tetra-ester derivatives of oxymorphone, similar to acetylation processes used with morphine and hydromorphone, though none of these variants were adopted for medical use. The drug was patented in the United States by Endo Pharmaceuticals in 1955 and received approval for medical use in 1959, when it was introduced to the American market under the brand name Numorphan. This name was derived by analogy to other opioid product names including Nucodan for oxycodone, Paramorphan for dihydromorphine, and Paracodin for dihydrocodeine.

    2012–2015

    Prior to 2012, oxymorphone was commonly administered via insufflation among recreational users. In 2012, Endo Pharmaceuticals introduced a reformulated extended-release version of Opana designed to be crush-resistant, intended to reduce abuse through nasal administration. However, this reformulation had unintended consequences as users adapted by dissolving the tablets and injecting them intravenously. In January 2013, the Centers for Disease Control and Prevention reported an illness cluster associated with intravenous abuse of Opana ER in Tennessee, presenting with symptoms resembling thrombotic thrombocytopenic purpura. Subsequently, in January 2015, the Indiana State Department of Health identified the first HIV outbreak directly linked to prescription opioid abuse in Scott County, a small rural community in southeastern Indiana. By late March 2015, Austin, Indiana had become the epicenter of an HIV outbreak traced to injectable use of the reformulated Opana ER. Research into these events determined that the crush-resistant reformulation paradoxically increased the risk of blood-borne infection transmission by driving users from nasal to intravenous administration, ultimately creating greater public health risks than those associated with injectable heroin or cocaine.

    2017–present

    In June 2017, amid the escalating opioid epidemic and evidence that the 2012 reformulation had failed to prevent illicit injection, the FDA took the unprecedented step of requesting that Endo Pharmaceuticals voluntarily remove reformulated Opana ER from the United States market. By July 6, 2017, Endo International complied with this request, marking a significant regulatory action in response to the opioid crisis. Generic versions of extended-release oxymorphone remain available in the United States.

    Effect Profile

    Curated + 81 Reports
    Opioid 8.1

    Strong euphoria, pain relief, and itching/nausea with moderate sedation

    Euphoria / Warmth×3
    109.1
    Analgesia×2
    105.6
    Sedation / Relaxation×1
    73.6
    Itching / Nausea×1
    109.5
    Catalog Erowid

    Empirical Duration

    Erowid Reports
    Onset Come Up Peak Offset
    Insufflated (16 reports)

    Tolerance & Pharmacokinetics

    drugs.wiki

    Tolerance Decay

    Full tolerance 1d Half tolerance 21d Baseline ~35d

    Cross-Tolerances

    Morphine
    80% ●○○
    Heroin
    80% ●○○
    Oxycodone
    80% ●○○
    Fentanyl
    80% ●○○
    Codeine
    80% ●○○
    Tramadol
    80% ●○○
    Kratom
    80% ●○○
    Methadone
    80% ●○○

    Experience Report Analysis

    Erowid BlueLight
    71 Reports
    2007–2014 Date Range
    37 With Age Data
    19 Effects Detected

    Demographics

    Gender Distribution

    Age Distribution

    Reports Over Time

    Effect Analysis

    Erowid + Bluelight

    Effects aggregated from 81 experience reports (71 Erowid + 10 Bluelight)

    81 Reports
    45 Effects Detected
    17 Positive
    15 Adverse
    13 Neutral

    Effect Sentiment Distribution

    Confidence Distribution

    Positive Effects 17

    Euphoria 56.8% 91%
    Empathy 29.6% 65%
    Sedation 29.6% 86%
    Contentment 20.0% 85%
    Relaxation 20.0% 85%
    Stimulation 19.7% 75%
    Pain Relief 17.3% 90%
    Anxiety Suppression 12.7% 70%
    Muscle Relaxation 10.0% 85%
    Visual Distortions 10.0% 70%
    Awe 10.0% 80%
    Bliss 10.0% 90%
    Joy 10.0% 80%
    Tactile Enhancement 9.9% 70%
    Body High 8.6% 83%
    Music Enhancement 6.1% 80%
    Focus Enhancement 5.6% 70%

    Adverse Effects 15

    Nausea 42.0% 80%
    Body Load 40.0% 80%
    Irritability 30.0% 80%
    Dizziness 20.0% 82%
    Vomiting 20.0% 95%
    Headache 14.8% 85%
    Stomach Cramps 10.0% 75%
    Tinnitus 10.0% 80%
    Motor Suppression 10.0% 75%
    Appetite Suppression 10.0% 70%
    Dysphoria 10.0% 80%
    Numbness 10.0% 90%
    Sweating 8.6% 85%
    Confusion 7.4% 75%
    Pupil Dilation 5.6% 70%

    Dose-Response Correlation

    How effect frequency changes across dose levels

    View data table
    Effect Strong (n=14) Heavy (n=21)
    Euphoria 57.1% 52.4%
    Nausea 42.9% 47.6%
    Hospital 28.6% 33.3%
    Empathy 28.6% 23.8%
    Sedation 28.6% 28.6%
    Sweating 28.6% 0%
    Stimulation 21.4% 23.8%
    Anxiety Suppression 14.3% 9.5%
    Pain Relief 0% 14.3%
    Headache 0% 9.5%
    Music Enhancement 0% 9.5%
    Body High 0% 9.5%
    Dissociation 0% 9.5%
    Focus Enhancement 0% 9.5%
    Tactile Enhancement 0% 9.5%

    Dose–Effect Mapping

    Experience Reports

    How reported effects shift across dose tiers, based on 71 experience reports.

    Limited tier coverage — most reports fall within the Strong / Heavy range. Effects at other dose levels may not be represented.

    Insufflated dose range: 10.0–20.0 mg (median 15.0 mg)
    Effect Strong (n=14) Heavy (n=21)
    euphoria
    57%
    52%
    nausea
    43%
    48%
    hospital
    29%
    33%
    empathy
    29%
    24%
    sedation
    29%
    29%
    sweating
    29%
    stimulation
    21%
    24%
    anxiety suppression
    14%
    10%
    pain relief
    14%
    headache
    10%
    music enhancement
    10%
    body high
    10%
    dissociation
    10%
    focus enhancement
    10%
    tactile enhancement
    10%

    Risk Escalation

    Sentiment Analysis

    Average frequency of positive vs adverse effects across dose tiers

    Strong n=14
    3 positive 35.7% 3 adverse 28.6%
    Heavy n=21
    8 positive 19.0% 3 adverse 22.2%
    View effect breakdown

    Adverse Effects

    Effect Strong (n=14) Heavy (n=21) Change
    Nausea
    43%
    48%
    10%
    Sweating
    29%
    0%
    Anxiety Suppression
    14%
    10%
    -33%
    Headache
    10%
    0%

    Positive Effects

    Effect Strong (n=14) Heavy (n=21) Change
    Euphoria
    57%
    52%
    -8%
    Empathy
    29%
    24%
    -16%
    Stimulation
    21%
    24%
    +11%
    Pain Relief
    14%
    0%
    Music Enhancement
    10%
    0%
    Body High
    10%
    0%
    Focus Enhancement
    10%
    0%
    Tactile Enhancement
    10%
    0%

    Dosage Distribution

    Dose distribution from experience reports

    Oral

    Median: 12.5 mg IQR: 10.0–30.0 mg n=11

    Insufflated

    Median: 15.0 mg IQR: 10.0–20.0 mg n=41

    Real-World Dose Distribution

    62K Doses

    From 83 individual dose entries

    Oral (n=14)

    Median: 20.0mg 25th: 10.0mg 75th: 30.0mg 90th: 30.0mg
    mg/kg median: 0.22 mg/kg 75th: 0.413

    Intravenous (n=6)

    Median: 10.0mg 25th: 5.5mg 75th: 22.75mg 90th: 33.5mg
    mg/kg median: 0.11 mg/kg 75th: 0.276

    Insufflated (n=59)

    Median: 12.5mg 25th: 10.0mg 75th: 20.0mg 90th: 30.0mg
    mg/kg median: 0.18 mg/kg 75th: 0.28

    Common Combinations

    Most co-occurring substances in experience reports

    Form / Preparation

    Most common forms and preparations reported

    Body-Weight Dosing

    Dose relative to body weight from reports with weight data

    Oral

    Median: 0.153 mg/kg IQR: 0.11–0.413 mg/kg n=11

    Insufflated

    Median: 0.184 mg/kg IQR: 0.134–0.304 mg/kg n=41

    Redose Patterns

    Redosing behavior across 64 reports

    23.4% Redosed
    1.3 Avg Doses
    60m Median Interval

    Opioid Equivalence (MME)

    NIH HEAL 2024 & CDC 2022
    ⚠ Citation & Disclaimer: Conversion factors sourced from the NIH HEAL Initiative MME Calculator (Adams et al., PAIN 2025), the CDC 2022 Clinical Practice Guideline for Prescribing Opioids for Pain, and the MDCalc MME Calculator. These are approximate equianalgesic ratios for educational reference only. Individual responses vary significantly based on genetics, tolerance, cross-tolerance, and route of administration. This is not medical advice. Do not use these conversions to adjust opioid dosing without professional medical guidance.
    3.3 mg Oxymorphone 10 mg Morphine (oral)
    MME factor 3.0×

    Oxymorphone 3.3 mg oral ≈ 10 mg Morphine oral

    Evidence level: Moderate (B).

    Legal Status

    Country Status Notes
    Germany Anlage II BtMG Controlled under the Betäubungsmittelgesetz (Narcotics Act). Manufacturing, importing, possessing, selling, or transferring without a license is prohibited. Anlage II classification permits restricted medical use under appropriate authorization.
    Russia Schedule I Classified as a Schedule I controlled substance under Russian drug control legislation. Possession, distribution, and manufacturing without authorization are prohibited.
    Switzerland Verzeichnis A Listed under Verzeichnis A in the Swiss controlled substances regulations. Medicinal use is permitted with appropriate authorization and licensing.
    United Kingdom Class A, Schedule 2 Controlled under the Misuse of Drugs Act 1971. As a Class A substance, it carries the most severe penalties for unauthorized possession, sale, or distribution. Schedule 2 designation permits medical use under strict controls.
    United States Schedule II Controlled under the Controlled Substances Act. Illegal to sell without a DEA license and illegal to buy or possess without a license or prescription. In 2017, the FDA requested Endo Pharmaceuticals to remove the extended-release formulation from the market due to concerns about opioid misuse and abuse associated with the injectable reformulation.
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