Codeine methylbromide

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Codeine methylbromide
Codeine methylbromide.png
Clinical data
Other namesCodeine bromomethylate, 125-27-9, DEA No. 9070
AHFS/Drugs.com Monograph
Legal status
Legal status
Identifiers
  • 7,8-Didehydro-17,17-dimethyl-4,5-α-epoxy-6α-hydroxy-3-methoxymorphinanium bromide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C19H24BrNO3
Molar mass 394.309 g·mol−1
3D model (JSmol)
  • C[N+]1(CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O)C.[Br-]
  • InChI=1S/C19H24NO3.BrH/c1-20(2)9-8-19-12-5-6-14(21)18(19)23-17-15(22-3)7-4-11(16(17)19)10-13(12)20;/h4-7,12-14,18,21H,8-10H2,1-3H3;1H/q+1;/p-1/t12-,13+,14-,18-,19-;/m0./s1 X mark.svgN
  • Key:KIKLDWULAZATJG-YZZSNFJZSA-M X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Codeine methylbromide (Eucodin) is the bromomethane (methylbromide) salt of codeine. Its possession is prohibited in many jurisdictions. It is considered a Schedule I controlled substance in the United States, with a DEA ACSCN of 9070 and nil annual aggregate manufacturing quota. [1] as of 2014. As it is used in a different way than basic salts of codeine like the phosphate or hydrochloride owing to its below-mentioned dual action, it is considered to be a different drug related to codeine rather than merely a salt of it in many contexts. [2]

Also known by the genericised trade name eucodeine, and the salt name also sometimes given as methobromide, this drug was first synthesised in Austria-Hungary in 1903. As it is a bromide in addition to a codeine salt, it has a dual mechanism of action and is indicated for pain with insomnia or nervousness and violent coughing. [2] This codeine-based bromide also has morphine, dihydrocodeine, dihydromorphine, hydromorphone, isocodeine, hydrocodone, and other such analogues; also, there are codeine-based barbiturates and salicylates. [3]

Related Research Articles

<span class="mw-page-title-main">Bromine</span> Chemical element, symbol Br and atomic number 35

Bromine is a chemical element with the symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.

<span class="mw-page-title-main">Morphine</span> Pain medication of the opiate family

Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies. It is mainly used as a pain medication, and is also commonly used recreationally, or to make other illicit opioids. There are numerous methods used to administer morphine: oral; sublingual; via inhalation; injection into a muscle; by injection under the skin; intravenously; injection into the space around the spinal cord; transdermal; or via rectal suppository. It acts directly on the central nervous system (CNS) to induce analgesia and alter perception and emotional response to pain. Physical and psychological dependence and tolerance may develop with repeated administration. It can be taken for both acute pain and chronic pain and is frequently used for pain from myocardial infarction, kidney stones, and during labor. Its maximum effect is reached after about 20 minutes when administered intravenously and 60 minutes when administered by mouth, while the duration of its effect is 3–7 hours. Long-acting formulations of morphine are available as MS-Contin, Kadian, and other brand names as well as generically.

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

Oxycodone, sold under various brand names such as Roxicodone and OxyContin, is a strong, semi-synthetic opioid used medically for treatment of moderate to severe pain. It is highly addictive and 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">Narcotic</span> Chemical substance with psycho-active properties

The term narcotic originally referred medically to any psychoactive compound with numbing or paralyzing properties. In the United States, it has since become associated with opiates and opioids, commonly morphine and heroin, as well as derivatives of many of the compounds found within raw opium latex. The primary three are morphine, codeine, and thebaine.

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

Hydromorphone, also known as dihydromorphinone, and sold under the brand name Dilaudid among others, is a morphinan opioid used to treat moderate to severe pain. Typically, long-term use is only recommended for pain due to cancer. It may be used by mouth or by injection into a vein, muscle, or under the skin. Effects generally begin within half an hour and last for up to five hours.

<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">Papaverine</span> Chemical compound

Papaverine is an opium alkaloid antispasmodic drug, used primarily in the treatment of visceral spasms and vasospasms, occasionally in the treatment of erectile dysfunction and acute mesenteric ischemia. While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the analgesic morphine and its derivatives.

The Convention for Limiting the Manufacture and Regulating the Distribution of Narcotic Drugs was a drug control treaty promulgated in Geneva on 13 July 1931 that entered into force on 9 July 1933.

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

Nalbuphine, sold under the brand names Nubain among others, is an opioid analgesic which is used in the treatment of pain. It is given by injection into a vein, muscle, or fat.

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

Rocuronium bromide is an aminosteroid non-depolarizing neuromuscular blocker or muscle relaxant used in modern anaesthesia to facilitate tracheal intubation by providing skeletal muscle relaxation, most commonly required for surgery or mechanical ventilation. It is used for standard endotracheal intubation, as well as for rapid sequence induction (RSI).

<span class="mw-page-title-main">Cyclizine</span> Antiemetic/motion sickness

Cyclizine, sold under a number of brand names, is a medication used to treat and prevent nausea, vomiting and dizziness due to motion sickness or vertigo. It may also be used for nausea after general anaesthesia or that which developed from opioid use. It is taken by mouth, in the rectum, or injected into a vein.

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

Butorphanol is a morphinan-type synthetic agonist–antagonist opioid analgesic developed by Bristol-Myers. Butorphanol is most closely structurally related to levorphanol. Butorphanol is available as the tartrate salt in injectable, tablet, and intranasal spray formulations. The tablet form is only used in dogs, cats and horses due to low bioavailability in humans.

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

Levorphanol is an opioid medication used to treat moderate to severe pain. It is the levorotatory enantiomer of the compound racemorphan. Its dextrorotatory counterpart is dextrorphan.

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

Thebacon, or dihydrocodeinone enol acetate, is a semisynthetic opioid that is similar to hydrocodone and is most commonly synthesised from thebaine. Thebacon was invented in Germany in 1924, four years after the first synthesis of hydrocodone. Thebacon is a derivative of acetyldihydrocodeine, where only the 6–7 double bond is saturated. Thebacon is marketed as its hydrochloride salt under the trade name Acedicon, and as its bitartrate under Diacodin and other trade names. The hydrochloride salt has a free base conversion ratio of 0.846. Other salts used in research and other settings include thebacon's phosphate, hydrobromide, citrate, hydroiodide, and sulfate.

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

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 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">Pentoxyverine</span> Antitussive / cough suppressant

Pentoxyverine (rINN) or carbetapentane is an antitussive commonly used for cough associated with illnesses like common cold. It is sold over-the-counter as Solotuss, or in combination with other medications, especially decongestants. One such product is Certuss, a combination of guaifenesin and pentoxyverine.

<span class="mw-page-title-main">Codeine</span> Opiate and prodrug of morphine used to treat pain

Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is also commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, Papaver somniferum. It is typically used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children or adults. In Europe, it is not recommended as a cough medicine in those under 12 years of age. It is generally taken by mouth. It typically starts working after half an hour, with maximum effect at two hours. Its effects last for about four to six hours. Codeine exhibits abuse potential similar to other opioid medications.

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

Benzylmorphine (Peronine) is a semi-synthetic opioid narcotic introduced to the international market in 1896 and that of the United States very shortly thereafter. It is much like codeine, containing a benzyl group attached to the morphine molecule just as the methyl group creates codeine and the ethyl group creates ethylmorphine or dionine. It is about 90% as strong as codeine by weight.

<span class="mw-page-title-main">Desomorphine</span> Semi-synthetic opioid, morphine analogue

Desomorphine is a semi-synthetic opioid commercialized by Roche, with powerful, fast-acting effects, such as sedation and analgesia. It was first discovered and patented by a German team working for Knoll in 1920 but was not generally recognized. It was later synthesized in 1932 by Lyndon Frederick Small. Small also successfully patented it in 1934 in the United States. Desomorphine was used in Switzerland under the brand name Permonid and was described as having a fast onset and a short duration of action, with relatively little nausea compared to equivalent doses of morphine. Dose for dose it is eight to ten times more potent than morphine.

Sodium salts are salts composed of a sodium cation and the conjugate base anion of some inorganic or organic acids. They can be formed by the neutralization of such acids with sodium hydroxide.

References

  1. "Conversion Factors for Controlled Substances". Diversion Control Division, Drug Enforcement Administration. U.S. Department of Justice.
  2. 1 2 Lowry WT, Garriott JC (1979). Forensic Toxicology: Controlled Substances and Dangerous Drugs. Boston, MA: Springer US. pp. 176–177. ISBN   978-1-4684-3444-6.
  3. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.). Whitehouse Station, N.J.: Merck. 2001. ISBN   978-0-911910-13-1.