Codeine methylbromide

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 428852152

| IUPAC_name = 7,8-Didehydro-17,17-dimethyl-4,5-α-epoxy-6α-hydroxy-3-methoxymorphinanium bromide

| image = Codeine methylbromide.png

| width = 180

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| Drugs.com = {{drugs.com|monograph|codeine}}

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| legal_US = Schedule I

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 125-27-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 25007U9T7H

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| PubChem = 5362447

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4515039

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = KIKLDWULAZATJG-YZZSNFJZSA-M

| C=19 | H=24 | Br=1 | N=1 | O=3

| 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-]

| synonyms = Codeine bromomethylate, 125-27-9, DEA No. 9070

}}

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.{{Cite web|url=http://deadiversion.usdoj.gov/quotas/conv_factor/index.html|title = Conversion Factors for Controlled Substances | work = Diversion Control Division, Drug Enforcement Administration | publisher = U.S. Department of Justice }} 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.{{cite book | vauthors = Lowry WT, Garriott JC |title=Forensic Toxicology: Controlled Substances and Dangerous Drugs |date=1979 |publisher=Springer US |location=Boston, MA |isbn=978-1-4684-3444-6 | pages = 176–177 | url = https://books.google.com/books?id=szDnBwAAQBAJ&dq=Codeine+methylbromide&pg=PP3 }}

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. This codeine-based bromide also has morphine, dihydrocodeine, dihydromorphine, hydromorphone, isocodeine, hydrocodone, and other such analogues; also, there are codeine-based barbiturates and salicylates.{{cite book |title=The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals |date=2001 |publisher=Merck |location=Whitehouse Station, N.J. |isbn=978-0-911910-13-1 |edition=13th}}