Nicodicodine

Nicodicodine
Clinical data
Other names	Nicodicodeine, 6-Nicotinoyldihydrocodeine, Nicodicodina, Nicodicodinum
Routes of; administration	Oral, intravenous
ATC code	none;
Legal status
Legal status	AU: S2 (Pharmacy medicine); BR: Class A2 (Narcotic drugs); DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; UN: Narcotic Schedules I and III;
Identifiers
	IUPAC name (5alpha,6alpha)-3-Methoxy-17-methyl-4,5-epoxymorphinan-6-yl pyridine-3-carboxylate;
CAS Number	808-24-2;
PubChem CID	5464304;
ChemSpider	4576612;
UNII	04G0T06UGT;
CompTox Dashboard (EPA)	DTXSID40230642 ;
ECHA InfoCard	100.011.241
Chemical and physical data
Formula	C24H26N2O4
Molar mass	406.482 g·mol−1
3D model (JSmol)	Interactive image;
	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;
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Nicodicodine is an opioid developed as a cough suppressant and analgesic.^[8] Synthesized in 1904, it is not commonly used, but has activity similar to other opioids.^[8] 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.

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[SIELC-1] [1]
"Nicodicodine [INN:BAN:DCF] | SIELC". www.sielc.com. 16 May 2018. Retrieved 12 January 2019.

[2] [2]
"Drugs Misuse Regulation 1987". www.legislation.qld.gov.au. Office of the Queensland Parliamentary Counsel. Retrieved 10 January 2019.

[3] [3]
Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-03.

[4] [4]
"Anlage II BtMG - Einzelnorm". www.gesetze-im-internet.de.

[5] [5]
"Misuse of Drugs Act 1971". www.legislation.gov.uk. Retrieved 10 January 2019.

[6] [6]
"The International Drug Control Conventions". undocs.org. United Nations. Retrieved 10 January 2019.

[7] [7]
"Chemistry Dashboard". comptox.epa.gov. U.S. Environmental Protection Agency. Retrieved 10 January 2019.

[Stolberb-8] [8]
Stolberg VB (2016). Painkillers: History, Science, and Issues. ABC-CLIO. p. 110. ISBN 978-1-4408-3532-2. Retrieved 12 January 2019.

[8]

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Nicodicodine

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Nicodicodine

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References

Clinical data


Other names	Nicodicodeine, 6-Nicotinoyldihydrocodeine, Nicodicodina,^[1] Nicodicodinum^[1]
Routes of administration	Oral, intravenous
ATC code	none
Legal status
Legal status	AU: S2 (Pharmacy medicine)^[2] BR: Class A2 (Narcotic drugs)^[3] DE: Anlage II (Authorized trade only, not prescriptible)^[4] UK: Class B^[5] UN: Narcotic Schedules I and III^[6]
Identifiers
IUPAC name (5alpha,6alpha)-3-Methoxy-17-methyl-4,5-epoxymorphinan-6-yl pyridine-3-carboxylate^[7]
CAS Number	808-24-2
PubChem CID	5464304
ChemSpider	4576612
UNII	04G0T06UGT
CompTox Dashboard (EPA)	DTXSID40230642
ECHA InfoCard	100.011.241
Chemical and physical data
Formula	C₂₄H₂₆N₂O₄
Molar mass	406.482 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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