14-Hydroxydihydrocodeine

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14-Hydroxydihydrocodeine
14-Hydroxydihydrocodeine.svg
14-Hydroxydihydrocodeine molecule ball.png
Identifiers
  • 3,14-dihydroxy-6-methoxy-4,5α-epoxy-17-methylmorphinan
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.208.390 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H23NO4
Molar mass 317.385 g·mol−1
3D model (JSmol)
  • COc5ccc1CC2C4(O)CCC(O)C3Oc5c1C34CCN2C
  • InChI=1S/C18H23NO4/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/h3-4,11,13,16,20-21H,5-9H2,1-2H3/t11-,13+,16-,17-,18+/m0/s1 Yes check.svgY
  • Key:LHTAJTFGGUDLRH-QMVVXIJUSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

14-Hydroxydihydrocodeine (RAM-318) is an opiate analgesic drug, which is also an active metabolite of oxycodone and hydromorphinol. [1] [2] 14-Hydroxydihydrocodeine is not currently marketed in any developed country, but has been of interest to pharmaceutical companies looking for new analgesics and antitussives.

Related Research Articles

<span class="mw-page-title-main">Hydrocodone</span> Opioid drug used in pain relief

Hydrocodone, also known as dihydrocodeinone, is a semisynthetic opioid used to treat pain and as a cough suppressant. It is taken by mouth. Typically it is dispensed as the combination acetaminophen/hydrocodone or ibuprofen/hydrocodone for pain severe enough to require an opioid and in combination with homatropine methylbromide to relieve cough. It is also available by itself in a long-acting form under the brand name Zohydro ER, among others, to treat severe pain of a prolonged duration. Hydrocodone is a controlled drug: in the United States a Schedule II Controlled Substance.

<span class="mw-page-title-main">Oxycodone</span> Opioid medication

Oxycodone, sold under various brand names such as Roxicodone and OxyContin, is a semi-synthetic opioid used medically for treatment of moderate to severe pain. It is highly addictive and is a commonly abused drug. It is usually taken by mouth, and is available in immediate-release and controlled-release formulations. Onset of pain relief typically begins within fifteen minutes and lasts for up to six hours with the immediate-release formulation. In the United Kingdom, it is available by injection. Combination products are also available with paracetamol (acetaminophen), ibuprofen, naloxone, naltrexone, and aspirin.

<span class="mw-page-title-main">Tramadol</span> Medication of the opioid type

Tramadol, sold under the brand name Ultram among others, is an opioid pain medication and a serotonin–norepinephrine reuptake inhibitor (SNRI) used to treat moderately severe pain. When taken by mouth in an immediate-release formulation, the onset of pain relief usually begins within an hour. It is also available by injection. It is available in combination with paracetamol (acetaminophen).

Oxycodone/paracetamol, sold under the brand name Percocet among others, is a fixed-dose combination of the opioid oxycodone with paracetamol (acetaminophen), used to treat moderate to severe pain.

ATC code N02Analgesics is a therapeutic subgroup of the Anatomical Therapeutic Chemical Classification System, a system of alphanumeric codes developed by the World Health Organization (WHO) for the classification of drugs and other medical products. Subgroup N02 is part of the anatomical group N Nervous system.

<span class="mw-page-title-main">Oxymorphone</span> Opioid analgesic drug

Oxymorphone 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 potential to be abused.

<span class="mw-page-title-main">Dihydrocodeine</span> Opioid

Dihydrocodeine is a semi-synthetic opioid analgesic prescribed for pain or severe dyspnea, or as an antitussive, either alone or compounded with paracetamol (acetaminophen) or aspirin. It was developed in Germany in 1908 and first marketed in 1911.

<span class="mw-page-title-main">Nicocodeine</span> Opioid analgesic and antitussive drug

Nicocodeine is an opioid analgesic and cough suppressant, an ester of codeine closely related to dihydrocodeine and the codeine analogue of nicomorphine. It is not commonly used in most countries, but has activity similar to other opiates. Nicocodeine and nicomorphine were synthesized in 1904, and introduced in 1957 by Lannacher Heilmittel of Austria. Nicocodeine is metabolised in the liver by demethylation to produce nicomorphine, also known as 6-nicotinoylmorphine, and subsequently further metabolised to morphine. Side effects are similar to those of other opiates and include itching, nausea and respiratory depression. Related opioid analogues such as nicomorphine and nicodicodeine were first synthesized. The definitive synthesis, which involves treating anhydrous codeine base with nicotinic anhydride at 130 °C, was published by Pongratz and Zirm in Monatshefte für Chemie in 1957, simultaneously with the two analogues in an article about amides and esters of various organic acids.

<span class="mw-page-title-main">Desmetramadol</span> Opioid painkiller medication

Desmetramadol, also known as O-desmethyltramadol (O-DSMT), is an opioid analgesic and the main active metabolite of tramadol. Tramadol is demethylated by the liver enzyme CYP2D6 to desmetramadol in the same way as codeine, and so similarly to the variation in effects seen with codeine, individuals who have a less active form of CYP2D6 will tend to have reduced analgesic effects from tramadol. Because desmetramadol itself does not need to be metabolized to induce an analgesic effect, it can be used in individuals with low CYP2D6 activity unlike tramadol.

<span class="mw-page-title-main">Tilidine</span> Synthetic opioid painkiller

Tilidine, Leart or tilidate is a synthetic opioid painkiller, used mainly in Belgium, Bulgaria, Germany, Luxembourg, South Africa and Switzerland for the treatment of moderate to severe pain, both acute and chronic. Its onset of pain relief after oral administration is about 10–15 minutes and peak relief from pain occurs about 25–50 minutes after oral administration.

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Tapentadol, brand names Nucynta among others, is a centrally acting opioid analgesic of the benzenoid class with a dual mode of action as an agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI). Analgesia occurs within 32 minutes of oral administration, and lasts for 4–6 hours.

<span class="mw-page-title-main">Nefopam</span> Analgesic medication

Nefopam, sold under the brand name Acupan among others, is a centrally acting, non-opioid painkilling medication, that is primarily used to treat moderate to severe pain.

<span class="mw-page-title-main">Hydromorphinol</span> Opioid analgesic drug

Hydromorphinol, is an opiate analogue that is a derivative of morphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated. It has similar effects to morphine such as sedation, analgesia and respiratory depression, but is twice as potent as morphine and has a steeper dose-response curve and longer half-life. It is used in medicine as the bitartrate salt and hydrochloride

An equianalgesic chart is a conversion chart that lists equivalent doses of analgesics. Equianalgesic charts are used for calculation of an equivalent dose between different analgesics. Tables of this general type are also available for NSAIDs, benzodiazepines, depressants, stimulants, anticholinergics and others.

<span class="mw-page-title-main">Opiate</span> Substance derived from opium

An opiate is an alkaloid substance derived from opium. It has a different meaning from the similar term opioid, used to designate all substances, both natural and synthetic, that bind to opioid receptors in the brain. Opiates are alkaloid compounds naturally found in the opium poppy plant Papaver somniferum. The psychoactive compounds found in the opium plant include morphine, codeine, and thebaine. Opiates have long been used for a variety of medical conditions, with evidence of opiate trade and use for pain relief as early as the eighth century AD. Most opiates are considered drugs with moderate to high abuse potential and are listed on various "Substance-Control Schedules" under the Uniform Controlled Substances Act of the United States of America.

<span class="mw-page-title-main">Hydrocodone/ibuprofen</span> Combination drug

Hydrocodone/ibuprofen (INNs), sold under the brand name Vicoprofen, is a fixed-dose combination analgesic medication used in short-term therapy to relieve severe pain. Vicoprofen combines the analgesic and antitussive properties of hydrocodone with the analgesic, anti-inflammatory, and antipyretic properties of ibuprofen. In contrast to hydrocodone/acetaminophen combination analgesics such as Vicodin, this hydrocodone/ibuprofen avoids some of the liver toxicity which may occur from acetaminophen, but still presents significant dangers in hydrocodone overdose, namely respiratory depression. Vicoprofen is supplied in a fixed dose combination tablet which contains hydrocodone bitartrate, USP 7.5 mg with ibuprofen, USP 200 mg. Additional strengths of generic Vicoprofen are now available, in combinations of 5 mg/200 mg and 10 mg/200 mg respectively.

Fentanyl/fluanisone is a veterinary combination drug consisting of fentanyl and fluanisone for use in mice, rats, rabbits and guinea pigs.

<span class="mw-page-title-main">Noroxymorphone</span> Chemical compound

Noroxymorphone is an opioid which is both a metabolite of oxymorphone and oxycodone and is manufactured specifically as an intermediate in the production of narcotic antagonists such as naltrexone and others. It is a potent agonist of the μ-opioid receptor, but is poorly able to cross the blood-brain-barrier into the central nervous system, and for this reason, has only minimal analgesic activity.

Oxycodone/ibuprofen is an oral combination drug formulation of the opioid analgesic oxycodone and the nonsteroidal anti-inflammatory drug (NSAID) ibuprofen that is used in the treatment of chronic and acute pain. This particular drug is supplied in a fixed dose combination tablet which contains Oxycodone Hydrochloride, USP 5 mg with Ibuprofen, USP 400 mg.

<span class="mw-page-title-main">Noroxycodone</span> Chemical compound

Noroxycodone is the major metabolite of the opioid analgesic oxycodone. It is formed from oxycodone in the liver via N-demethylation predominantly by CYP3A4. Noroxycodone binds to and activates the μ-opioid receptor (MOR) similarly to oxycodone, although with one-third of the affinity of oxycodone and 5- to 10-fold lower activational potency. However, although a potent MOR agonist, noroxycodone poorly crosses the blood-brain-barrier into the central nervous system, and for this reason, is only minimally analgesic in comparison.

References

  1. Ginsburg D (1959). "Some recent advances in the chemistry of the opium alkaloids". UNODC Bulletin on Narcotics (3).
  2. Ishida T, Oguri K, Yoshimura H (1979). "Isolation and identification of urinary metabolites of oxycodone in rabbits". Drug Metabolism and Disposition. 7 (3): 162–5. PMID   38087.