Oxycodone

(5R,9R,13S,14S)-4,5α-epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one

Overview

Oxycodone belongs to Opioids.

Key safety note: Oxycodone is a strong opioid and its central danger is dose-dependent respiratory depression, the usual mechanism of opioid death, which is greatest in opioid-naïve people, at higher doses, and above all when it is combined with other CNS depressants (benzodiazepines, alcohol, gabapentinoids, other opioids), a combination that carries an FDA boxed warning.[4][3]
Effects
Subjective effects vary. What a substance feels like depends on dose, individual physiology, mindset, and setting. The points below describe commonly reported effects, not guaranteed, uniform, or desirable outcomes.
  • Pain relief with a warm relaxation and, especially at higher or non-oral doses, euphoria and calm detachment. Drowsiness and clouded thinking.
  • Physical signs: pinpoint pupils, slowed breathing, itch, nausea/vomiting and constipation.
  • With regular use: tolerance to the euphoria and analgesia (but not to constipation), physical dependence, and an unpleasant flu-like withdrawal on stopping.
Dosing & duration
Harm-reduction note: These are commonly cited reference ranges, not a recommendation or a “safe” dose. Potency, purity, body chemistry, tolerance, and drug combinations vary widely. Start low, go slow, wait for full effects before redosing, and never assume an unknown product matches these figures. Missing data is not evidence of safety.

Oral (immediate- and controlled-release), and by injection (IV/IM/subcutaneous): clinician-prescribed and titrated. Figures below are clinical context, NOT a recreational guide.. Oxycodone is a prescription strong opioid. Dosing is individualised and titrated to effect and tolerance, with very different doses in opioid-naïve versus opioid-tolerant patients. There is no safe recreational dose: the amount that produces euphoria in a naïve person overlaps with the amount that stops their breathing, and the danger multiplies with any other depressant. Controlled-release tablets must be swallowed whole: crushing them to snort or inject releases the full dose at once and frequently kills. Oral oxycodone is roughly 1.5× as potent as oral morphine. Have naloxone available. Never use alone.

Dose ranges

Oral IR (opioid-naïve adult, clinical)

≈5–15 mg every 4–6 h, titrated

Controlled-release (OxyContin)

≈10 mg every 12 h, swallowed whole, titrated

Equianalgesic reference

Oral oxycodone ≈ 1.5× oral morphine

Duration

onset

IR ≈10–30 min, oral ≈30–60 min

total

IR analgesia ≈4–6 h (controlled-release ≈12 h)

after effects

Sedation/constipation may persist. Withdrawal on cessation after regular use

Chemical & Physical Properties
FormulaC18H21NO4
Molar mass315.36 g/mol
StateSolid
Melting point219 °C
Boiling pointNot reported
DensityNot reported
Vapor pressureNot reported
pKa8.53
LogP0.7
Solubility166mg/mL, Insoluble in water, Nearly insoluble in water
Refractive indexNot reported
Identifiers & Synonyms
CAS76-42-6
CAS (enantiomer)
PubChem CID5284603
InChIKeyBRUQQQPBMZOVGD-XFKAJCMBSA-N
InChIInChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1
SMILESCN1CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O

Synonyms

  • OxyContin
  • Oxycodone
  • Roxicodone
  • Dihydrohydroxycodeinone
  • Oxy
  • Percs
Pharmacodynamics & Biochemistry

Oxycodone is a semi-synthetic opioid made from thebaine (a poppy alkaloid). It is an agonist at the μ-opioid receptor (MOR), with much weaker activity at the κ- and δ-opioid receptors. Like other opioids it acts through Gi/Go signalling to reduce neuronal excitability and neurotransmitter release along pain pathways, producing analgesia together with euphoria, sedation, pinpoint pupils, cough suppression, constipation and, the dangerous effect, depression of the brainstem respiratory drive (reversible by naloxone). It is itself an active opioid of moderate MOR affinity. Clinically it is somewhat more potent than oral morphine (roughly 1.5×), helped by a high oral bioavailability (~60–90%) and good CNS penetration. It is metabolised in the liver by CYP2D6 to oxymorphone (a much more potent MOR agonist, usually a minor contributor to the overall effect) and by CYP3A4 to noroxycodone (weakly active), because of the CYP2D6 and CYP3A4 routes, genetic variation and interacting drugs can meaningfully change its effect. At the receptor level it binds the μ-opioid receptor with Kᵢ ≈18 nM and far more weakly at the δ (≈958 nM) and κ (≈677 nM) receptors. Oxycodone became central to the prescription-opioid crisis: aggressive marketing of the controlled-release product OxyContin from the late 1990s, and the crushing of those tablets to defeat the slow-release and snort or inject the full dose, drove widespread dependence, overdose and a later shift to heroin and illicit fentanyl.

Biological targets

  • MOR

Binding & functional measurements

TargetMeasurementSpecies
KORpKi 6.17
DORpKi 6.02
μ-opioid receptorKi 26 nMHuman
Pharmacokinetics
BioavailabilityOral ≈60–87%
TmaxImmediate-release ≈1–1.5 h
Half-life≈3–5 h
Vd≈2.6 L/kg
Protein binding≈45%
MetabolismHepatic CYP3A4 to noroxycodone and CYP2D6 to active oxymorphone
ExcretionRenal
Toxicology & Safety
Harm-reduction note: Toxicity and risk depend on dose, route, purity, combinations, setting, and individual health factors. Missing harms should never be interpreted as evidence of safety.

Not reported

Oxycodone is a strong opioid and its central danger is dose-dependent respiratory depression, the usual mechanism of opioid death, which is greatest in opioid-naïve people, at higher doses, and above all when it is combined with other CNS depressants (benzodiazepines, alcohol, gabapentinoids, other opioids), a combination that carries an FDA boxed warning. Overdose (pinpoint pupils, unconsciousness, slow or absent breathing) is a medical emergency reversible with naloxone. It has a high abuse and dependence potential: with repeated use, tolerance and physical dependence develop, and stopping abruptly causes an opioid withdrawal syndrome (agitation, aches, sweating, gastrointestinal upset, craving). Crushing or dissolving controlled-release tablets to snort or inject them delivers the whole dose at once and is a frequent cause of fatal overdose, as is co-use with alcohol or benzodiazepines. Constipation, nausea, sedation and itch are common. Risk is higher in the elderly, in respiratory disease, and with CYP2D6/CYP3A4-interacting drugs. It should not be used with MAOIs. Never use non-medically alone. Have naloxone available.[4][3]

Legal Status
Legal note: Legal status can change over time and may vary by country, region, formulation, analogue status, prescription context, and enforcement practice. Always confirm with current official sources before relying on this section.
Interactions & Contraindications

Drug interactions

Benzodiazepines, Alcohol, Gabapentinoids (gabapentin, pregabalin) Life-threatening additive respiratory depression and sedation (FDA boxed warning), the leading cause of opioid death.[3]
CYP3A4 inhibitors (ritonavir, azole antifungals, macrolides, grapefruit) Azole antifungals, macrolides, ritonavir or grapefruit raise oxycodone exposure.[3]
CYP3A4 inducers (rifampicin, carbamazepine) Rifampicin or carbamazepine reduce oxycodone exposure.[3]
Strong CYP2D6 inhibitors (e.g. paroxetine, fluoxetine) CYP2D6 inhibitors, or poor and ultra-rapid metaboliser genotypes, alter formation of the active metabolite oxymorphone.[4][3]
MAOIs, Other serotonergic drugs Risk of severe reactions or serotonin toxicity.[3]

Contraindications

Significant respiratory depression or acute severe asthma or acute/severe asthma in an unmonitored setting.[3]
Paralytic ileus or gastrointestinal obstruction paralytic ileus or known GI obstruction.[3]
Concurrent MAOI, SSRI/SNRI or other serotonergic medication concurrent or recent (within 14 days) MAOI use.[3]
Head injury or raised intracranial pressure head injury or raised intracranial pressure.[3]
Kidney or liver impairment severe impairment, and caution in the elderly.[3]
Combining with alcohol or other CNS depressants[3]
Usage & Context
  • A widely used strong opioid analgesic for moderate-to-severe acute pain (after surgery or injury), cancer pain and palliative care: given as immediate-release tablets/liquid and as 12-hourly controlled-release tablets (OxyContin), sometimes combined with paracetamol or naloxone.
  • Also heavily misused: it is one of the opioids most associated with the prescription-opioid epidemic, diverted and taken orally, insufflated or injected for euphoria.
  • Sold under many names (OxyContin, Roxicodone, Percocet with paracetamol) and known on the street as 'oxy' or 'percs'.
Sources & Evidence

Further Information