Ethylmorphine

Title: Ethylmorphine
CAS Registry Number: 76-58-4
CAS Name: 7,8-Didehydro-4,5-epoxy-3-ethoxy-17-methylmorphinan-6-ol
Molecular Formula: C19H23NO3
Molecular Weight: 313.39
Percent Composition: C 72.82%, H 7.40%, N 4.47%, O 15.32%
Literature References: Prepd by ethylation of morphine: Baizer, Ellner, J. Am. Pharm. Assoc. 39, 581 (1950); Gorecki, Ann. Pharm. (Poznan) 7, 21 (1969). Toxicity data: M. Aurousseau, J. Navarro, Ann. Pharm. Fr. 15, 640 (1957).
Properties: Crystals from ethanol, mp 199-201°.
Melting point: mp 199-201°
Derivative Type: Hydrochloride dihydrate
CAS Registry Number: 6746-59-4
Trademarks: Codethyline (Houd?
Molecular Formula: C19H23NO3.HCl.2H2O
Molecular Weight: 385.88
Percent Composition: C 59.14%, H 7.31%, N 3.63%, O 20.73%, Cl 9.19%
Properties: White to faintly yellow crystalline powder, mp about 123° (dec); anhydrous form, mp about 170° (dec). One gram dissolves in 10 ml water and in 25 ml alcohol; slightly sol in chloroform, ether. LD50 in mice: 264.6 mg/kg s.c.; 0.771 g/kg orally (Aurousseau, Navarro).
Melting point: mp about 123° (dec); mp about 170° (dec)
Toxicity data: LD50 in mice: 264.6 mg/kg s.c.; 0.771 g/kg orally (Aurousseau, Navarro)
Derivative Type: Methiodide
CAS Registry Number: 6696-59-9
Additional Names: Ethyl-N-methylmorphinium iodide
Trademarks: Trachyl
Molecular Formula: C19H23NO3.CH3I
Molecular Weight: 455.33
Percent Composition: C 52.76%, H 5.76%, N 3.08%, O 10.54%, I 27.87%
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.
Therap-Cat: Analgesic (narcotic); antitussive.
Therap-Cat-Vet: Analgesic (narcotic); antitussive; mydriatic.
Keywords: Analgesic (Narcotic); Antitussive.
Ethylnorepinephrine Ethylparaben Ethylstibamine Ethynodiol Ethynylbenzene

Ethylmorphine
Ethylmorphine.svg
Systematic (IUPAC) name
7,8-didehydro-4,5-α-epoxy- 3-ethoxy-17-methylmorphinan-6-α-ol
Clinical data
AHFS/Drugs.com International Drug Names
Legal status Schedule II (Single-Entity), Schedule III (In Combination Products)
Identifiers
CAS number 76-58-4 YesY
ATC code R05DA01 S01XA06
PubChem CID 5359271
DrugBank DB01466
ChemSpider 4514250 YesY
UNII RWO67D87EU YesY
Chemical data
Formula C19H23NO3 
Mol. mass 313.391 g/mol
 YesY (what is this?)  (verify)

Ethylmorphine (also known as codethyline, dionine, and ethyl morphine) is an opiate narcotic analgesic (pain killer).

Ethylmorphine was invented in Germany at Merck in 1884 and was used as a weaker alternative to heroin for all indications. Chemically, ethylmorphine is a morphine molecule with a -OC2H5 group substituted for the aromatic 3-OH group. Therefore the closest chemical relative of ethylmorphine is codeine, also known as methylmorphine. Ethylmorphine also has a hydromorphone analogue (ethyldihydromorphinone or 3-ethoxy-7,8-dihydro-morphin-6-one), and a dihydromorphine analogue known as ethyldihydromorphine (CID:5492914), although none of them appears to be commercially distributed at the current time.

As is the case with all narcotic analgesics, ethylmorphine is potentially habit-forming and can generate drug dependence of the codeine type. In most countries and internationally ethylmorphine and codeine are regulated much the same way. Like codeine, dihydrocodeine and similar weak opioid drugs, ethylmorphine is listed under the international Single Convention on Narcotic Drugs in Schedule III, which leads to some ethylmorphine preparations being available over the counter in some countries. In the US, ethylmorphine, like its methyl analog codeine, is controlled under the Controlled Substances Act, Schedule II as a pure compound and Schedule III when combined with non-opioid analgesics such as paracetamol (akin to US Schedule III paracetamol/codeine combinations sold under the brand name Tylenol 3/4). In theory, cough syrup containing ethylmorphine is listed in US Schedule V, meaning that it can be bought without prescription in certain states if the patient presents ID and/or the chemist knows the person and the patient signs a dispensary log that is monitored by the DEA. However, there are currently no ethylmorphine-based pharmaceuticals marketed in the US, making this a moot point; codeine-based products, on the other hand, are still relatively common.