:Desocodeine

{{Chembox

| ImageFile = Desocodeine.svg

| ImageSize = 180px

| IUPACName = 3-Methoxy-17-methyl-4,5α-epoxymorphinan

| SystematicName = (4R,4aR,7aS,12bS)-9-Methoxy-3-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline

| OtherNames = Dihydrodeoxycodeine

|Section1={{Chembox Identifiers

| CASNo = 3990-01-0

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4H4T7H4YKS

| PubChem = 5492803

| ChemSpiderID = 4591151

| SMILES = O(c2c1O[C@@H]5[C@@]34c1c(cc2)C[C@@H](N(CC3)C)[C@@H]4CCC5)C

| InChI = 1/C18H23NO2/c1-19-9-8-18-12-4-3-5-15(18)21-17-14(20-2)7-6-11(16(17)18)10-13(12)19/h6-7,12-13,15H,3-5,8-10H2,1-2H3/t12-,13+,15-,18+/m0/s1

| InChIKey = ZJWPQUSUXBOTPF-SCGCMHLBBV

| StdInChI = 1S/C18H23NO2/c1-19-9-8-18-12-4-3-5-15(18)21-17-14(20-2)7-6-11(16(17)18)10-13(12)19/h6-7,12-13,15H,3-5,8-10H2,1-2H3/t12-,13+,15-,18+/m0/s1

| StdInChIKey = ZJWPQUSUXBOTPF-SCGCMHLBSA-N

}}

|Section2={{Chembox Properties

| C=18 | H=23 | N=1 | O=2

| Appearance =

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|Section3={{Chembox Hazards

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Desocodeine is a potent semi-synthetic opioid which is the penultimate intermediate in the manufacture of desomorphine from codeine.{{Cite web |last=PubChem |title=Desocodeine |url=https://pubchem.ncbi.nlm.nih.gov/compound/5492803 |access-date=2022-11-15 |website=pubchem.ncbi.nlm.nih.gov |language=en}}{{Cite web |title=Desocodeine {{!}} C18H23NO2 {{!}} ChemSpider |url=http://www.chemspider.com/Chemical-Structure.4591151.html |access-date=2022-11-15 |website=www.chemspider.com}} Desocodeine is a potent analgesic, being as potent as morphine. It is partially metabolized into desomorphine, among others, after parenteral and oral administration.{{cite journal |vauthors=Eddy NB |date=1 November 1935 |title=STUDIES OF MORPHINE, CODEINE AND THEIR DERIVATIVES X. DESOXYMORPHINE-C, DESOXYCODEINE-C AND THEIR HYDROGENATED DERIVATIVES |journal=Journal of Pharmacology and Experimental Therapeutics |volume=55 |issue=1 |pages=257–267 |doi= |pmc= |pmid= |s2cid=93217792 }}{{cite journal |vauthors=Himmelsbach Clifton K|title=STUDIES OF CERTAIN ADDICTION CHARACTERISTICS OF (a) DIHYDROMORPHINE ("PARAMORPHAN"), (b) DIHYDRODESOXYMORPHINE-D ("DESOMORPHINE"), (c) DIHYDRODESOXYCODEINE-D ("DESOCODEINE"), AND (d) METHYLDIHYDROMORPHINONE ("METOPON")|journal=Journal of Pharmacology and Experimental Therapeutics|year=1939|volume=67|pages=239–249|s2cid=102042333 }}

Since 1936, desocodeine has been classified in the US as a Schedule I controlled substance under the Controlled Substances Act, indicating that the FDA has determined that there are no legal medicinal uses for it.{{Cite web | url=http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | title=DEA Diversion Control Division | access-date=4 May 2015 | archive-date=4 March 2016 | archive-url=https://web.archive.org/web/20160304053357/http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | url-status=dead }}

In Canada, desocodeine is classified as a Schedule I drug under the Controlled Drugs and Substances Act.

File:Synthesis of Desomorphine from Codein.svg

References

Category:Opioids