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| Other names | 6-Nicotinoylcodeine |
| Routes of administration | Oral, intravenous |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.020.900 |
| Chemical and physical data | |
| Formula | C24H24N2O4 |
| Molar mass | 404.466 g·mol−1 |
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Nicocodeine (Lyopect, Tusscodin) is anopioidanalgesic andcough suppressant, anester ofcodeine closely related todihydrocodeine and the codeine analogue ofnicomorphine. It is not commonly used in most countries, but has activity similar to other opiates. Nicocodeine andnicomorphine 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 tomorphine. Side effects are similar to those of otheropiates and includeitching,nausea andrespiratory depression. Relatedopioidanalogues such asnicomorphine andnicodicodeine were first synthesized. The definitive synthesis, which involves treating anhydrous codeine base with nicotinic anhydride at 130 °C, was published by Pongratz and Zirm inMonatshefte für Chemie in 1957,[2] simultaneously with the two analogues in an article about amides and esters of various organic acids.[2][3]
Nicocodeine is almost always used as the hydrochloride salt, which has a free base conversion ratio of .917. In the past, the tartrate, bitartrate, phosphate, hydrobromide, methiodide, hydroiodide, and sulfate were used in research or as pharmaceuticals.
Nicocodeine is regulated in most cases as is codeine and similar weak opiate drugs likeethylmorphine,benzylmorphine,dihydrocodeine and its other close derivatives likeacetyldihydrocodeine (although not the strongerhydrocodone oroxycodone, which are regulated like morphine) and others of this class in the laws of countries and the Single Convention On Narcotic Drugs. One notable example is the fact that nicocodeine is a Schedule I/Narcotic controlled substance in the United States along with heroin as nicocodeine was never introduced for medical use in the United States.
Nicodicodeine is a similar drug which is to nicocodeine as dihydrocodeine is to codeine. The metabolites of nicodicodeine includedihydromorphine where nicocodeine is turned into morphine as noted above.
Nicocodeinecough medicines are available as syrups, extended-release syrups, and sublingual drops. Analgesic preparations are also in the form of sublingual drops and tablets for oral administration. Nicocodeine is approximately the same strength ashydrocodone; it has a faster onset of action.
The 2013 DEA annual production quota for nicocodeine and its two related drugs are zero. Nicocodeine's ACSCN is 9309. Nicodicodeine is not assigned an ACSCN and is presumably controlled as either an ester ofdihydromorphine or derivative ofnicomorphine.