Oxycodone is an opioid analgesic drug derived from thebaine, an alkaloid in opium. It is more potent than morphine but has similar effects. Recreational use carries potential dangers, chief among which are the amounts of acetaminophen consumed when taking a preparation that combines the narcotic analgesia of oxycodone with an NSAID.
Introduction to Oxycodone[/FLOAT_LEFT]
Oxycodone is an opioid derived from thebaine, an alkaloid in opium. Like other opioids, it has analgesic, sedative, and anxiolytic properties. It is among the most oftenn prescribed drugs for pain managment and has several incarnations, both with and without added APAP.
Uses of OxycodoneTherapeutically, it is used for the treatment of moderate to severe pain. This includes post-op pain, pain management for chronic, physical issues (like degenerative disc disease, for example).
Recreationally, its euphoric, numbing effects make it a favorite among experimentalists and addicts alike, as does the ability to dose with far more precision than with street product (as pills contain exact milligram amounts). Its wide availability in US pain clinics and Mexican pharmacies and the ease with which such powerful meds can be acquired make it a popular opioid around the world, though its use, both recreational and therapeutic, is most prevalent in the Western Hemisphere.
Routes of Administration
Swallowing OxycodoneOxycodone is most commonly taken orally when combined with APAP, as the best therapeutic approach to managing pain is to use a narcotic pain reliever in combination with an NSAID to reduce inflammation. Unlike many other drugs (specifically opioids), it has a relatively high oral bioavailability (60-80%) due to low first pass metabolism.
Many oxycodone tablets also contain APAP, which causes liver damage and should be removed from oxycodone tablets before oral ingestion. which can be done by Cold Water Extraction, as oxycodone is more soluble in cold water than APAP, so the former stays in solution, while the latter falls to the bottom, i.e. precipitates. The resulting solution is usually taken orally, due to the large volume of water used to filter the oxycodone/apap tablets.
Oxycodone tablets without any APAP are much smaller and can be snorted, even though the bioavailability of oxycodone intranasally is about 45%, much lower than oral administration. Used by many because the high comes on much quicker and more powerful, but with this length of the high is reduced drastically. Many users are more concerned with their individual rituals (and most began their habit with snorting a pill here and there), and getting the drug to hit as hard and fast as possible. Usually snorting is caused by impatience and in some cases necessity, (I.E. when pain is extreme and near instant relief is ideal.)
snorting is just as bad as IV use, the latter usually leading to the former. The risks are mostly the same albeit sharing straws begets hepatitis, and when done too often, can damage the nasal septum.
Threads about snorting Oxycodone
Threads about injecting Oxycodone
Plugging OxycodoneThreads about plugging Oxycodone
Effects of OxycodoneEffects of oxycodone include: analgesia, anxiolysis, sedation, euphoria, miosis (pupil constriction), nausea, dizziness, itching, dry mouth, sexual dynsfunction, somnolence (nodding) and respiratory depression. Adverse effects usually increase as dose increases.
Combinations with OxycodoneOxycodone is potentiated by and can potentiate other opiates/opioids, benzodiazepines, alcohol and other central nervous system (CNS)depressants.
Basic harm reduction when combining opiates/opioids with other CNS depressants:
The last point is arguably the most important, along with having a sober/lucid friend on hand to speak up if you seem to be underestimating your level of intoxication.
- Research and have an informed plan for dosing, noting effects, and having a dosing schedule to keep track of how much and what is used.
- Have a lucid friend present to help you realistically evaluate your level of intoxication. This is one of the simplest yet most highly effective steps in harm reduction is simple yet highly effective in preventing a bad situation when combining (even smaller-than-normal) doses of an opiate/opioid with another CNS depressant.
- Be familiar with each drug, its effects, and how you respond at commonly used dosages independently before attempting any combinations, then administer each dose of each drug separately. This way, if an adverse effect arises, isolating the problem is more feasible.
- Start low and dose up: take the lowest dose you think you need and cut that number in half. Dosing up is always possible, whereas the reverse usually requires a trip to the ER.
oxycodone and stimulants
Oxycodone and alcohol: This is a dangerous combination. Risk of severe respiratory depression is increased, however the combination has been anecdotally championed as enjoyable. Sedation, relaxation, will be increased. Higher doses might induce nausea. Smaller doses of each are mandatory.
Oxycodone and benzodiazepines: Like with alcohol, risk of respiratory depression is increased. Sedation, relaxation will be increased. Smaller doses of each are mandatory.
Pharmacology of Oxycodone
Oxycodone, like many other opioids, is a mu, k, and d-opioid receptor agonist. Binding of oxycodone to its receptors, which are G-coupled, causes hyperpolarization of its cells. Adenylyl cyclase system is inhibited, and cyclic AMP is decreased. GABA release is increased. Oxycodone's affinity and subsequent binding to kappa and mu-opioid receptors is responsible for its antinociceptive effects. Oxycodones affinity for these receptors is 1/10 to 1/40th that of morphine.
Pharmacokinetics: Oxycodone's structure allows it to avoid serious first-pass metabolism. In the liver, oxycodone is metabolized to its more potent metabolite, oxymorphone (about 11% of dose), by O-demethylation mediated by CYP3A, and to noroxycodone and noroxymorphone (about 45% of dose) by N-demethylation mediated by CYP2D6. Poor CYP2D6 metabolizers (4-10% of Caucasians) might experience less effects from oxycodone.
Half life: 3-6 hours
Bioavailability: 60-87% orally, 61.6% +/- 30.2% rectally, 46% intranasally, 45.4% +/- 20.1% sublingual
Time to maximum serum concentrations: 1 hour
The dangers of Oxycodone
-underestimating a pharm
Chemistry of Oxycodone
Column 1 Column 2 Systematic(IUPAC) name: (5R,9R,13S,14S)-4,5-alpha-epoxy-14-hydroxy-3-methoxy-17-methyl-morphinan-6-one Synonyms: 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxymorphine, dihydrohydroxycodeinone14-hydroxydihydrocodeinone, Dihydrone; Dinarkon, Eubine, Eukodal, OxyContin, Oxygesic, Oxynorm, Supeudol (hydrochloride); Proladone (Pectinate) Molecular Formula: C18H21NO4, C18H21NO4.HCl (hydrochloride), C18H21NO4 Molar mass: 315.36 g/mol, 351.83 g/mol (hydrochloride) CAS Registry Number: 76-42-6, 124-90-3 (hydrochloride), 9012-92-4 (pectinate) Melting Point: 218-220°C Boiling Point: no data Flash Point: no data Solubility: Freebase soluble in alcohol, chloroform; practically insoluble in ether, water, KOH, NaOH, ammonia. Hydrochloride 1 g dissolves in 6-7 mL water; slightly soluble in alcohol Additionnal data: Freebase pKa 8.53. Hydrochloride decomposes at 270-272°C; partition coefficient (octanol/water) 0.7 Notes: Freebase aspect : long rods; crystallized from alcohol; Hydrochloride aspect long rods; crystallized from water. Pectinate used for prolonged action
Oxycodone hydrochloride is the form of oxycodone used in Percocet and Perocedan.
Producing OxycodoneTwo ways are reported for the synthesis of oxycodone :
1- Starting from thebaïne which is oxidized by hydrogen peroxide in formic acid into 14-hydroxycodeinone, which is subsequently hydrogenated to yield oxycodone.
2- Oxidation of codeine with sodium dichromate in acetic acid.
Forms of OxycodoneOxycodone is the active opioid ingredient in brand names such as Percocet, Endocet, Oxycontin, Roxicet and Roxicodone
OxyContin vs Roxicodone vs Oxycodone
There is a lot of confusion about OxyContin particularly, one can assume this is because the name is so similar to oxycodone. OxyContin is not a drug, it is a brand name for a preparation of oxycodone. Oxycodone is the active chemical in OxyContin, the rest is fillers (otherwise some pills would be tiny), binders, or substances which create the time-release mechanism. The same goes for Roxicodone, and other common preparations. Some preparations, such as Percocet, also contain acetaminophen to prevent abuse or supposedly to contribute to pain relief, although if one is on prescription painkillers it is likely that acetaminophen is not strong enough to treat the pain one is experiencing.
IR vs CR
OxyIR is oxycodone hydrochloride and fillers/binders. It is designed for acute treatment of pain, and is an immediate release formulation, meaning as soon as it is ingested it goes to work. OxyContin is designed for longer lasting analgesia, releasing the drug over a period of about 12 hours. It contains an outer colored coating, which, contrary to popular belief, is not the time release mechanism. The colored coating is just a system so that ingredients can be easily recognized. The time release mechanism is a wax matrix inside which "suspends" the oxycodone. Even after removing the coating, the pill must be crushed to defeat the mechanism to make it suitable for insufflation or injecting.
Oxycodone comes in a variety of forms:
OxyIR (oxycodone hydrochloride): 5 mg, 10 mg, 20 mg (Canada)
Roxicodone (generic oxycodone hydrochloride): 5 mg (white, recently ceased), 15 mg (green), 30 mg (blue); 5mg/5ml oral solution; 20mg/ml concentrate
Percocet (oxycodone hydrochloride/acetaminophen, Canada and US): 2.5 mg/325 mg (pink oval), 5 mg/325 mg (blue round), 7.5 mg/325 mg (peach oval), 7.5mg/500 mg (peach capsule-shaped), 10 mg/325 mg (yellow capsule-shaped), 10 mg/650 mg (yellow oval), 10 mg/1000 mg (blue oval)
Percodan (oxycodone hydrochloride/aspirin, US only): 5 mg/325 mg
OxyNorm (oxycodone hydrochloride solution): 5, 10, or 20 mg capsules; 5 mg/5 ml, 250 ml bottles (Australia, NZ, UK), 10mg/ml and 50mg/ml injection solution (NZ, UK)
Depalgos (oxycodone hydrochloride/acetaminophen, Italy): 5 (yellow), 10 (pink), and 20 (red) mg/325 mg
Endone (oxycodone hydrochloride): 5 mg tablet (round, white) (Australia)
OxyContin (oxycodone hydrochloride and time release mechanism): 5 mg (blue, only available in Canada and the UK), 10 mg (white, Canada, US, UK), 15 mg (grey, US), 20 mg (pink, Canada, US, UK), 30 mg (brown, US), 40 mg (tan, Canada, US, UK), 60 mg (red, US), and 80 mg (green, Canada, US, UK), 160 mg used to be available but was taken off shelves due to a few accidental deaths and because of "diversion" problems.
OxyContin OP (US)/OxyNeo (Canada) (oxycodone hydrocloride and time release mechanism) reformulated version of original OxyContin, available in the same doses. This formulation of OxyContin was designed to be more difficult to abuse. It gels upon contact with water, which makes it unsuitable for injection, and retains much of its time release mechanism even if it is broken apart. OxyContin OP was released in the US in mid-2010 and OxyNeo will have completely replaced the old formula in Canada by the end of Spring 2012.
Legal status of Oxycodone
Oxycodone is a controlled substance 21 CFR 1308.12
CanadaOxycodone is Schedule I in Canada. Schedules in Canada are much different than those in the USA.
USAOxycodone is Schedule II in the United States. This means it is illegal to sell without a DEA license and illegal to buy or possess without a license or prescription.
EUOxycodone is Schedule II/Class A in the U.K., making it illegal to buy or possess without a prescription.
AUOxycodone is Schedule 8 (labelled "Controlled Drug") in Australia, making it illegal to buy or possess without a prescription. In addition to the prescription, it requires authority from Medicare to dispense. This puts it in the same category as morphine, methadone, fentanyl and ketamine.
History of Oxycodone
Popularity of Oxycodone over time
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***organize into formal citation format
 Synthesis of Essential Drugs, 1st edition, Ruben Vardanyan & Victor Hruby, Elsevier
Merck Index, fifteenth edition (2013)