Hydromorphone
4,5α-epoxy-3-hydroxy-17-methylmorphinan-6-one
Overview
Hydromorphone belongs to Opioids.
Effects
- At therapeutic doses: strong relief of moderate-to-severe pain, with drowsiness, nausea, constipation and pinpoint pupils.
- At higher (recreational) doses: intense opioid euphoria, warmth and relaxation, particularly rapid and pronounced when injected, alongside heavy sedation, itching and slowed breathing.
- Effects begin within minutes when injected (about 15–30 minutes orally) and last roughly 4–6 hours. The fast, intense onset of injected hydromorphone drives both its abuse liability and its overdose risk.
Dosing & duration
Oral (tablets/solution) and parenteral (IV/IM/subcutaneous). Also rectal. Medical injectable use is common. Non-medical use is oral, insufflated or injected.. Hydromorphone is highly potent, active in single-milligram amounts and roughly 5× morphine, so small dosing errors matter and it is very dangerous to opioid-naïve users. The oral figures below are commonly cited recreational reference ranges, not a recommendation or a 'safe' dose. Injected, the same amount acts far faster and more intensely, sharply raising overdose risk. Never combine with alcohol or other depressants, and remember that tolerance to euphoria outpaces tolerance to respiratory depression.
Dose ranges
0.5 mg
1–2 mg
2–4 mg
4–8 mg
8 mg +
Duration
Injected: within minutes, oral: 15–30 minutes
4–6 hours
Sedation and constipation. Tolerance and physical dependence with repeated use
Chemical & Physical Properties
| Formula | C17H19NO3 |
| Molar mass | 285.34 g/mol |
| State | Solid |
| Melting point | 266–267 °C |
| Boiling point | Decomposes at 305 °C |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | 8.2 |
| LogP | 1.06 |
| Solubility | Highly soluble, In water, 1,931 mg/L at 25 °C, Freely soluble in alcohol. Very soluble in chloroform |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 466-99-9 |
| CAS (enantiomer) | |
| PubChem CID | 5284570 |
| InChIKey | WVLOADHCBXTIJK-YNHQPCIGSA-N |
| InChI | InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1 |
| SMILES | CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3C(=O)CC4 |
Synonyms
- Dihydromorphinone
- Dilaudid
- Palladone
- Hydromorphone
Pharmacodynamics & Biochemistry
Hydromorphone (Dilaudid) is a potent semi-synthetic opioid derived from morphine, used for moderate-to-severe pain. It is roughly 5–7 times more potent than morphine and is also the active metabolite formed when hydrocodone is broken down by CYP2D6. It is available orally and, importantly, as an injectable widely used in hospital and palliative care. It is a strong, full agonist at the μ-opioid receptor (MOR), with weaker activity at the κ- and δ-opioid receptors. MOR activation in the CNS produces analgesia, sedation, euphoria and pupillary constriction and depresses the brainstem respiratory centres (the mechanism of fatal overdose), while peripheral MOR activation slows gut motility and causes constipation. Unlike many opioids, hydromorphone is not metabolised by the cytochrome-P450 system: it is cleared mainly by hepatic glucuronidation to hydromorphone-3-glucuronide (H3G). H3G has no opioid analgesic activity but is neuro-excitatory and accumulates in kidney impairment, where it can cause agitation, myoclonus and seizures. Its high potency means active doses are small, giving a narrow margin for error. Parenteral (injected) use produces a rapid, intense onset that carries high overdose and dependence risk.
Biological targets
- MOR
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| μ-opioid receptor | Ki 0.37 nM | Human |
| κ receptor | pKi 8.6 | Human |
| δ receptor | pKi 7.4 | Human |
Pharmacokinetics
| Bioavailability | Oral ≈30–55% |
| Tmax | Not reported |
| Half-life | ≈2–3 h |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic glucuronidation to hydromorphone-3-glucuronide |
| Excretion | Renal |
Toxicology & Safety
Not reported
Hydromorphone is a high-potency opioid with a narrow margin between an effective and a lethal dose: respiratory depression is the principal hazard, and the risk is especially high in opioid-naïve people and when it is injected. It is greatly amplified by alcohol, benzodiazepines and other CNS depressants. Because active doses are only a few milligrams, dosing errors and unfamiliarity with its potency are dangerous. It produces tolerance and physical dependence, is widely diverted and misused (including by injection, with associated infection risks), and in kidney impairment its metabolite H3G can accumulate and cause agitation, myoclonus and seizures. Naloxone reverses overdose.[4][3]
Legal Status
US: Schedule II. UK: Class A. DE: BtMG Anlage III
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- A hospital and palliative-care mainstay for severe acute and chronic pain (brand name Dilaudid), given orally or by injection, and useful when high opioid potency in a small volume is needed.
- Widely diverted and misused for its strong euphoria, frequently by injection, which adds risks of infection and vein damage.
- The active metabolite of hydrocodone, and one of the more sought-after prescription opioids on the illicit market.
Sources & Evidence
- Wentland MP, Lou R, Lu Q, et al. (2009). Syntheses of novel high affinity ligands for opioid receptors. Bioorg Med Chem Lett 19:2289-94.
PMID 19282177 · doi:10.1016/j.bmcl.2009.02.078
- PubChem: Hydromorphone (CID 5284570) — identifiers & computed properties
- FDA / DailyMed: Hydromorphone prescribing information — pharmacokinetics & metabolism
- Abi-Aad KR, Derian A. Hydromorphone. StatPearls [Internet] (NCBI Bookshelf, NBK470393) — pharmacology, medical use & toxicity
- PsychonautWiki: Hydromorphone — recreational dosage & duration CC BY-SA 4.0
- Wikipedia: Hydromorphone (pharmacology, pharmacokinetics & legal status) CC BY-SA 4.0
- DEA Diversion Control Division: Controlled Substance Schedules (hydromorphone is Schedule II)
- GOV.UK: Controlled drugs list (Misuse of Drugs legislation) — hydromorphone is Class A OGL v3.0
- Anlage III BtMG — Betäubungsmittelgesetz (hydromorphone listing)
- Volpe DA, McMahon Tobin GA, Mellon RD, et al. (2011). Uniform assessment and ranking of opioid μ receptor binding constants for selected opioid drugs. Regul Toxicol Pharmacol 59:385-90.
PMID 21215785 · doi:10.1016/j.yrtph.2010.12.007
- IUPHAR/BPS Guide to PHARMACOLOGY (GtoPdb) CC BY-SA 4.0