Oxymorphone
Also called Opana, Oximorphonum, 14-Hydroxydihydromorphinone, Dihydrohydroxymorphinone
Part of the metabolic pathway of Oxycodone and Oxymorphone. See the timeline on the metabolic highway.
Enzymes that break it down: CYP3A4. Wikipedia’s drug infobox says: “Liver (CYP3A4, glucuronidation)” (revision 1368817590).
Dosage
Oral bands as drawn from PsychonautWiki's ranges below. The table is the source of truth.
When sources disagree, both rows are shown as published. Nothing is averaged or merged.
Oral
| Source | Threshold | Light | Common | Strong | Heavy |
|---|---|---|---|---|---|
| PsychonautWiki | 2.5 mg PW | 5–10 mg PW | 10–20 mg PW | 20–30 mg PW | 30 mg+ PW |
| TripSit | – | 5–7.5 mg TS | 10–20 mg TS | – | 20 mg+ TS |
Insufflated
TripSit dose text
TripSit's factsheet also states its doses as text.
Oral Low: 5-7.5mg Common: 10-20mg Heavy: 20mg+ | Insufflated Low: 2-4mg Common: 4-6mg Heavy: 6-10mg+ TS
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Duration
| Route · source | Onset | Come-up | Peak | Offset | Total | After-effects |
|---|---|---|---|---|---|---|
| Oral · PsychonautWiki | 20–45 minutes PW | – | – | – | 4–6 hours PW | – |
TripSit factsheet
Mixing
For best safety practice, don't mix this drug with other depressants.
Why: respiratory depression. PsychonautWiki says:
- “Respiratory depression (also known as hypoventilation) can be described as a reduced urge to breathe that can be fatal depending on its intensity.” (PsychonautWiki, Respiratory depression, revision 150612)
- “... otherwise safe dosages of these compounds can become fatal when combined with even small amounts of other classes of depressant. For example, benzodiazepines combined with opioids are an extremely common cause of fatal respiratory depression. It is therefore strongly discouraged to combine these depressants at any dosage range.” (PsychonautWiki, Respiratory depression, revision 150612)
- “The most common cause of substance-related deaths is the combination of depressants (such as opiates, benzodiazepines, or alcohol) with other depressants.” (PsychonautWiki, Responsible drug use, revision 168206)
- “This combination potentiates the muscle relaxation, amnesia, sedation, and respiratory depression caused by one another. At higher doses, it can lead to a sudden, unexpected loss of consciousness along with a dangerous amount of depressed respiration.” (PsychonautWiki, dangerous interactions table, "Depressants" row, revision 156847)
Quotes from PsychonautWiki, CC BY-SA 4.0.
Acute combinations: what happens when these are taken close together. Entries backed by a medical journal or agency are listed first.
Backed by medical journals
PsychonautWiki also lists dangerous combinations shared across a whole group (opioids) in a table this page does not copy. Read that list on PsychonautWiki.
TripSit combination chart
TripSit rates each pairing. Only pairings with a number carry a citation from TripSit. See the whole chart; TripSit's own notes are on combo.tripsit.me.
Risks and toxicity
Like most opioids, unadulterated oxymorphone does not cause many long-term complications other than dependence and constipation. Outside of the extremely powerful addiction and physical dependence, the harmful or toxic aspects of oxymorphone usage are exclusively associated with not taking appropriate precautions in regards to its administration, overdosing and using impure products.[11] PW
Heavy dosages of oxymorphone can result in respiratory depression, leading onto fatal or dangerous levels of anoxia (oxygen deprivation). This occurs because the breathing reflex is suppressed by agonism of µ-opioid receptors proportional to the dosage consumed. PW
Oxymorphone can also cause nausea and vomiting; a significant number of deaths attributed to opioid overdose are caused by aspiration of vomit by an unconscious victim. This is when an unconscious or semi-conscious user who is lying on their back vomits into their mouth and unknowingly suffocates. It can be prevented by ensuring that one is lying on their side with their head tilted downwards so that the airways cannot be blocked in the event of vomiting while unconscious (also known as the recovery position). PW
Opioid overdoses can be treated by calling the local emergency number and administering an opioid antagonist such as naloxone. PW
It is strongly recommended that one use harm reduction practices when using this drug. PW
Tolerance and addiction potential
As with other opiate-based painkillers, the chronic use of oxymorphone can be considered extremely addictive and is capable of causing both physical and psychological dependence. When physical dependence has developed, withdrawal symptoms may occur if a person suddenly stops their usage. PW
Tolerance to many of the effects of oxymorphone develops with prolonged use, including therapeutic effects. This results in users having to administer increasingly large doses to achieve the same effects. The rate at which this occurs develops at different rates for different effects with tolerance to the constipation-inducing effects developing particularly slowly. Oxymorphone presents cross-tolerance with all other opioids, meaning that after the consumption of oxymorphone all opioids will have a reduced effect. PW
The risk of fatal opioid overdoses rise sharply after a period of cessation and relapse, largely because of reduced tolerance. To account for this lack of tolerance, it is safer to only dose a fraction of one's usual dosage if relapsing. It has also been found that the environment one is in can play a role in opioid tolerance. In one scientific study, rats with the same history of heroin administration were significantly more likely to die after receiving their dose in an environment not associated with the drug in contrast to a familiar environment.[12]
Dangerous interactions
Oxymorphone is dangerous to use in combination with other depressants as many fatalities reported as overdoses are caused by interactions with other depressant drugs like alcohol or benzodiazepines, resulting in dangerously high levels of respiratory depression.[14] PW
TripSit factsheet
Testing
Effects
EuphoriaDry MouthMood liftItchinessRelaxantConstipationPupil constrictionAnalgesia TS
Overview
Oxymorphone (also known by the brand name Opana) is a semi-synthetic opioid analgesic used in the management of moderate to severe pain, and is similar in structure to other opioids such as morphine and heroin. Oxymorphone was first developed in Germany in 1914and introduced to the American market in 1959. Unlike many other opioids, oxymorphone is almost devoid of antitussive properties. Oxymorphone is an important precursor to other opioids and opioid antagonists such as naloxone.[1]
A powerful semisynthetic opioid analgesic also known as opana. A derivative of morphine it is approximately ten times as potent. Has a low oral bioavailability, and as such it is usually insufflated or taken rectally. TS
Oxymorphone, sold under the brand names Numorphan and Opana among others, is a highly potent opioid analgesic indicated for treatment of severe pain. Pain relief after injection begins after about 5–10 minutes; after oral administration it begins after about 30 minutes and lasts about 3–4 hours for immediate-release tablets and 12 hours for extended-release tablets. The elimination half-life of oxymorphone is much faster intravenously, and as such, the drug is most commonly used orally. Like oxycodone, which metabolizes to oxymorphone, oxymorphone has a high abuse potential.[4]
Oxymorphone was developed in Germany in 1914. It was patented in 1955 and approved for medical use in 1959. In June 2017 the FDA asked Endo Pharmaceuticals to remove its product from the US market. This was in part due to the opioid epidemic in the US, and the fact that a 2012 reformulation failed to stop illicit injection of the drug. Endo responded by voluntarily removing Opana ER from the market a month later. Generic versions of extended-release oxymorphone, such as those manufactured by Amneal Pharmaceuticals, are still available in the US.[7–10] WP
History
History
Oxymorphone was first developed in Germany in 1914, and patented in the US by Endo Pharmaceuticals in 1955. It was introduced in the United States in January 1959 and other countries around the same time.[15]
Legal status
- Germany: Oxymorphone is controlled under BtMG Anlage II, making it illegal to manufacture, import, possess, sell, or transfer it without a license.[18] PW
- Russia: Oxymorphone is a Schedule I controlled substance.[19] PW
- Switzerland: Oxymorphone is a controlled substance specifically named under Verzeichnis A. Medicinal use is permitted.[20] PW
- United Kingdom: Oxymorphone is a Class A, Schedule 2 drug in the United Kingdom.[21] PW
- United States: Oxymorphone is a Schedule II Controlled Substance in the United States.[22] PW
Brand names
- Numorphan (suppository and injectable solution) WP
- Opana ER (extended-release tablet): June 2017 FDA removal request due to rates of IV abuse.[9] WP
- Opana IR (immediate-release tablet) WP
- O-Morphon in Bangladesh by Ziska pharmaceutical ltd. WP
The brand name Numorphan is derived by analogy to the Nucodan name for an oxycodone product (or vice versa) as well as Paramorphan/Paramorfan for dihydromorphine and Paracodin (dihydrocodeine). The only commercially available salt of oxymorphone in most of the world at this time is the hydrochloride, which has a free base conversion ratio of 0.891, and oxymorphone hydrochloride monohydrate has a factor of 0.85.[23] WP
Generic pill markings are ATV10/APO; HK10 (10 mgs) oblong white and ATV20/APO; HK20 (20 mgs) oblong white. WP⚠ Wikipedia itself has flagged this text: citation needed.
Pharmacology
Pharmacodynamics
Oxymorphone elicits its effects by binding to and activating the μ-opioid receptor (MOR) and, to a much lesser extent, the δ-opioid receptor (DOR) and κ-opioid receptor (KOR). Its activity at the DOR may augment its action at the MOR. Oxymorphone is 10 times more potent than morphine.[17]
1.02 mg of oxymorphone hydrochloride produces analgesia roughly equivalent to 10 mg of morphine sulfate, with similar peak and duration of effect but potentially slightly fewer side effects at equipotent doses.[26] WP⚠ A table follows this text in the source and is not copied here. Open the source to see it.
Receptor binding · Wikipedia
Oxymorphone at opioid receptors
Every row cites [24]
| Affinities (Kᵢ (Inhibitor constant)) | |||
|---|---|---|---|
| MOR (μ-Opioid receptor) | DOR (δ-Opioid receptor) | KOR (κ-Opioid receptor) | MOR:DOR:KOR |
| 0.78 nM | 50 nM | 137 nM | 1:64:176 WP⚠ The source table has only this one row. |
Chemistry
- Formula
- C17H19NO4 PC
- CAS number
- 76-41-5 PC
- Molar mass (g/mol)
- 301.34 PC
- IUPAC name (computed by PubChem)
- (4R,
4aS, PC7aR, 12bS) - 4a, 9- dihydroxy- 3- methyl- 2, 4, 5, 6, 7a, 13- hexahydro- 1H- 4, 12- methanobenzofuro[3, 2- e] isoquinolin- 7- one - SMILES
- CN1CC[C@]
23[C@@H] PC4C(=O) CC[C@] 2([C@H] 1CC5=C3C(=C(C=C5) O) O4) O - InChIKey
- UQCNKQCJZOAFTQ-
ISWURRPUSA- PCN - PubChem CID
- 5284604
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References
- Journal / agency The Essence of Analgesia and Analgesics. 2010. doi:10.1017/CBO9780511841378
- Journal / agency Opioids in Cancer Pain. May 2009. doi:10.1093/med/9780199236640.001.0001
- Journal / agency Brayfield, A. “Oxymorphone Hydrochloride”. Martindale: The Complete Drug Reference. Pharmaceutical Press. 3 September 2014. doi:10.7748/en.22.5.12.s13
- Journal / agency Sloan P. Review of oral oxymorphone in the management of pain. Therapeutics and Clinical Risk Management. August 2008. doi:10.2147/tcrm.s1784 · PMID 19209260 · PMC2621383
- Journal / agency Smith HS. Clinical Pharmacology of Oxymorphone. Pain Medicine. 1 April 2009. doi:10.1111/j.1526-4637.2009.00594.x
- Journal / agency Babalonis S, Lofwall MR, Nuzzo PA, Walsh SL. Pharmacodynamic effects of oral oxymorphone: abuse liability, analgesic profile and direct physiologic effects in humans. Addiction Biology. January 2016. doi:10.1111/adb.12173 · PMID 25130052 · PMC4383736
- Other Fischer J, Ganellin CR. Analogue-based Drug Discovery. 2006
- Journal / agency Wolf LK. FDA takes aim at opioid epidemic. Chemical & Engineering News. 19 June 2017
- Journal / agency Office of the Commissioner. Press Announcements – FDA requests removal of Opana ER for risks related to abuse. 10 September 2019
- Other Bernstein L, Merle R. Six drug companies subpoenaed in federal opioids probe. 27 November 2019
- Other Merck Manual of Home Health Handbook – 2nd edition, 2003, p. 2097
- Other Why Heroin Relapse Often Ends In Death - Lauren F Friedman (Business Insider)
- Journal / agency Siegel, S., Hinson, R. E., Krank, M. D., McCully, J. Heroin “Overdose” Death: Contribution of Drug-Associated Environmental Cues. Science. 23 April 1982. doi:10.1126/science.7200260
- Journal / agency Darke, S., Zador, D. Fatal heroin “overdose”: a review. Addiction (Abingdon, England). December 1996. doi:10.1046/j.1360-0443.1996.911217652.x
- Other Sinatra R. The Essence of Analgesia and Analgesics. 2010
- Other Morphine derivative
- Other Davis MP, Glare PA, Hardy J. Opioids in Cancer Pain. 2009
- Other Anlage II BtMG - Einzelnorm
- Other Постановление Правительства РФ от 01.10.2012 N 1002 (ред. от 09.08.2019)
- Other Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien
- Other List of most commonly encountered drugs currently controlled under the misuse of drugs legislation
- Other Drug Enforcement Administration Controlled Substances
- Other Oxymorphone Hydrochloride. 30 January 2013
- Journal / agency Corbett AD, Paterson SJ, Kosterlitz HW. Opioids. 1993. doi:10.1007/978-3-642-77460-7_26
- Journal / agency Prommer E. Oxymorphone: a review. Supportive Care in Cancer. February 2006. doi:10.1007/s00520-005-0917-1 · PMID 16317569
- Journal / agency Eddy NB, Lee LE. The analgesic equivalence to morphine and relative side action liability of oxymorphone (14-hydroxydihydro morphinone). The Journal of Pharmacology and Experimental Therapeutics. February 1959. doi:10.1016/S0022-3565(25)12962-5 · PMID 13631610
Text and values on this page are quoted from PsychonautWiki (CC BY-SA 4.0), Wikipedia (CC BY-SA 4.0), TripSit factsheets, PubChem (public domain). Each value links to the exact revision it came from.