Codeine methylbromide

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]

Codeine methylbromide
Clinical data
Other namesCodeine bromomethylate, 125-27-9, DEA No. 9070
AHFS/Drugs.comMonograph
Legal status
Legal status
  • US: Schedule I
Identifiers
IUPAC name
  • 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
FormulaC19H24BrNO3
Molar mass394.309 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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 N
  • Key:KIKLDWULAZATJG-YZZSNFJZSA-M N
 NY (what is this?)  (verify)

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]

References
  1. "Conversion Factors for Controlled Substances". Diversion Control Division, Drug Enforcement Administration. U.S. Department of Justice.
  2. Lowry WT, Garriott JC (1979). Forensic Toxicology: Controlled Substances and Dangerous Drugs. Boston, MA: Springer US. p. 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.


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