Structure via PubChem · Public domain (PubChem)
nicocodine
Sign in to saveNicocodeine (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 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 to morphine. Side effects are similar to those of other opiates and in
Chemical data
- Formula
- C24H24N2O4
- Molecular weight
- 404.5 g/mol
- IUPAC name
- [(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] pyridine-3-carboxylate
- SMILES
- CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)OC(=O)C6=CN=CC=C6
- InChIKey
- RYBGRHAWFUVMST-MJFIPZRTSA-N
- XLogP
- 2.3
- Polar surface area
- 60.9 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 404.174
Show 4 more facts
- chemical formula
- C₂₄H₂₄N₂O₄
- canonical SMILES
- CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)OC(=O)C6=CN=CC=C6
- isomeric SMILES
- CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)OC(=O)C6=CN=CC=C6
- Commons category
- Nicocodeine
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
1 sectionsContents
- References
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 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 to morphine. Side effects are similar to those of other opiates and include itching, nausea and respiratory depression. 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.
Excerpted from Wikipedia’s “nicocodine” article, available under the CC BY-SA 4.0 licence.