Nicodicodeine

Nicodicodeine

Clinical data
Routes of administration	Oral, intravenous
ATC code	none
Legal status
Legal status	DE: Anlage II (Prohibited) US: Schedule I
Identifiers
IUPAC name (5α,6α)-3-Methoxy-17-methyl-4,5-epoxymorphinan-6-yl nicotinate
Synonyms	6-Nicotinoyldihydrocodeine
CAS Number	808-24-2
PubChem (CID)	5464304
ChemSpider	4576612
ECHA InfoCard	100.011.241
Chemical and physical data
Formula	C24H26N2O4
Molar mass	406.474 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O[C@@H]4[C@@H]5Oc1c2c(ccc1OC)C[C@H]3N(CC[C@]25[C@H]3CC4)C)c6cccnc6
InChI InChI=1S/C24H26N2O4/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/h3-5,7,10,13,16-17,19,22H,6,8-9,11-12H2,1-2H3/t16-,17+,19-,22-,24-/m0/s1 Key:GTGRMWCOZHEYRL-MJFIPZRTSA-N
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Nicodicodeine is an opioid developed as a cough suppressant and analgesic. Synthesized in 1904, it is not commonly used, but has activity similar to other opioids. Nicodicodeine is metabolised in the liver by demethylation to produce 6-nicotinoyldihydromorphine, and subsequently further metabolised to dihydromorphine. Since the final active metabolite is the slightly stronger opiate dihydromorphine rather than morphine, nicodicodeine can be expected to be marginally more potent and longer acting than nicocodeine. Side effects are similar to those of other opioids and include itching, nausea and respiratory depression.

References