Nicodicodine

Nicodicodine is an opioid developed as a cough suppressant and analgesic.[7] Synthesized in 1904, it is not commonly used, but has activity similar to other opioids.[7] Nicodicodine 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, nicodicodine 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.

Nicodicodine
Clinical data
Other namesNicodicodeine, 6-Nicotinoyldihydrocodeine, Nicodicodina,[1] Nicodicodinum[1]
Routes of
administration		Oral, intravenous
ATC code
  • none
Legal status
Legal status
  • AU: S2 (Pharmacy medicine) [2]
  • DE: Anlage II (Authorized trade only, not prescriptible) [3]
  • UK: Class B [4]
  • UN: Narcotic Schedules I and III [5]
Identifiers
IUPAC name
  • (5alpha,6alpha)-3-Methoxy-17-methyl-4,5-epoxymorphinan-6-yl pyridine-3-carboxylate[6]
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.011.241
Chemical and physical data
FormulaC24H26N2O4
Molar mass406.482 g·mol−1
3D model (JSmol)
SMILES
  • CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(CC4)OC(=O)C6=CN=CC=C6
InChI
  • 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
 NY (what is this?)  (verify)

References
  1. "Nicodicodine [INN:BAN:DCF] | SIELC". www.sielc.com. 16 May 2018. Retrieved 12 January 2019.
  2. "Drugs Misuse Regulation 1987". www.legislation.qld.gov.au. Office of the Queensland Parliamentary Counsel. Retrieved 10 January 2019.
  3. "Anlage II BtMG - Einzelnorm". www.gesetze-im-internet.de.
  4. "Misuse of Drugs Act 1971". www.legislation.gov.uk. Retrieved 10 January 2019.
  5. "The International Drug Control Conventions". undocs.org. United Nations. Retrieved 10 January 2019.
  6. "Chemistry Dashboard". comptox.epa.gov. U.S. Environmental Protection Agency. Retrieved 10 January 2019.
  7. Stolberg VB (2016). Painkillers: History, Science, and Issues. ABC-CLIO. p. 110. ISBN 978-1-4408-3532-2. Retrieved 12 January 2019.


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