Nicocodeine (Lyopect, Tusscodin) is an opioid

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

and

cough suppressant Cold medicines are a group of medicinal, medications taken individually or in Combination drug, combination as a Symptomatic treatment, treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The t ...

, an ester of

codeine 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 use ...

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 Hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (''hypo'' meaning "below") to perform needed respiratory gas exchange. By definition it causes an increased concentration of carbon dioxide (hypercapnia ...

. 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. 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 like

ethylmorphine Ethylmorphine (also known as codethyline, dionine, and ethyl morphine) is an opioid analgesic and antitussive. Side effects Adverse effects are similar to other opioids and include drowsiness, constipation, vertigo, nausea, vomiting, and respirat ...

benzylmorphine 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 mole ...

, dihydrocodeine and its other close derivatives like

acetyldihydrocodeine Acetyldihydrocodeine is an opiate derivative discovered in Germany in 1914 and was used as a cough suppressant and analgesic. It is not commonly used, but has activity similar to other opiates. Acetyldihydrocodeine is a very close relative deri ...

(although not the stronger hydrocodone or oxycodone, 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 include

dihydromorphine Dihydromorphine (Paramorfan, Paramorphan) is a semi-synthetic opioid structurally related to and derived from morphine. The 7,8-double bond in morphine is reduced to a single bond to get dihydromorphine.Rama Rao Nadendla. Principles Of Organic ...

where nicocodeine is turned into morphine as noted above. Nicocodeine cough 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 as hydrocodone; 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 of

or derivative of nicomorphine.

References

{{Opioidergics 4,5-Epoxymorphinans Mu-opioid receptor agonists Nicotinate esters Phenol ethers Semisynthetic opioids