Nicocodeine

Nicocodeine

Clinical data
Routes of administration	Oral, intravenous
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage II (Prohibited) UK: Class B US: Schedule I
Identifiers
IUPAC name (5α,6α)-3-methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-yl nicotinate
Synonyms	6-Nicotinoylcodeine
CAS Number	3688-66-2 Y
PubChem CID	5463872
ChemSpider	4576411 Y
UNII	DYX391P13E
ECHA InfoCard	100.020.900
Chemical and physical data
Formula	C24H24N2O4
Molar mass	404.458 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O[C@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(OC)ccc3C4)C)c6cccnc6
InChI InChI=1S/C24H24N2O4/c1-26-11-9-24-16-6-8-19(29-23(27)15-4-3-10-25-13-15)22(24)30-21-18(28-2)7-5-14(20(21)24)12-17(16)26/h3-8,10,13,16-17,19,22H,9,11-12H2,1-2H3/t16-,17+,19-,22-,24-/m0/s1 Y Key:RYBGRHAWFUVMST-MJFIPZRTSA-N Y
NY (what is this?)

Nicocodeine (Lyopect, Tusscodin) is an opioid analgesic and cough suppressant, an ester of codeine 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. The drug was first synthesised in the first years of the 20th Century in what was then the Austro-Hungarian Empire, as were nicomorphine and nicodicodeine.

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 sulphate were used in research or as pharmaceuticals.

Nicocodeine is regulated in most cases as is codeine and similar weak opiate drugs like ethylmorphine, benzylmorphine, dihydrocodeine and its other close derivatives like acetyldihydrocodeine (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.