Codeine hydrochloride

Base Information

• Chemical Name: Codeine hydrochloride
• CAS No.: 1422-07-7
• Molecular Formula: C18H21NO3•ClH
• Molecular Weight: 335.831
• European Community (EC) Number: 215-829-5
• UNII: 406LPJ779Q
• ChEMBL ID: CHEMBL1257022
• DSSTox Substance ID: DTXSID7048904
• Mol file: 1422-07-7.mol

Synonyms:CODEINE HYDROCHLORIDE;1422-07-7;Codeine HCl;Codeine.HCl;DTXSID7048904;406LPJ779Q;(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-ol;hydrochloride;(4R,4Ar,7S,7aR,12bS)-9-methoxy-3-methyl-1,2,3,4,4a,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-ol;chloride;EINECS 215-829-5;UNII-406LPJ779Q;codeinhydrochlorid;Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, hydrochloride (1:1), (5?,6?)-;Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, hydrochloride, (5?,6?)- (9CI);Morphinan-6?-ol, 7,8-didehydro-4,5?-epoxy-3-methoxy-17-methyl-, hydrochloride (8CI);Codeine hydrochloride;Codeinium chloride;3-Methoxy-Morphanin HCl;NCGC00247720-01;SCHEMBL548093;CHEMBL1257022;DTXCID4028830;Codeine.HCl, 1mg/ml in Methanol;NUXLENPAZQNFAM-FFHNEAJVSA-N;CODEINE HYDROCHLORIDE [MI];Tox21_112884;CODEINE HYDROCHLORIDE ANHYDROUS;AKOS022180452;CODEINE HYDROCHLORIDE [WHO-DD];Morphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-, hydrochloride;CAS-1422-07-7;NS00080699;Q27258297;(4R,4aR,7S,7aR,12bS)-9-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol hydrochloride;MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, HYDROCHLORIDE (1:1), (5.ALPHA.,6.ALPHA.)-

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Chemical Property of Codeine hydrochloride

Chemical Property:

• Vapor Pressure: 2.47E-09mmHg at 25°C
• Melting Point: ~280° with some decompn
• Boiling Point: 462°Cat760mmHg
• Flash Point: 233.2°C
• PSA: 41.93000
• Density: g/cm³
• LogP: 2.24100
• Storage Temp.: 2-8°C
• Solubility.: Soluble in water, slightly soluble in ethanol (96 per cent), practically insoluble in cyclohexane.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 335.1288213
• Heavy Atom Count: 23
• Complexity: 509

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O.Cl
• Isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O.Cl
• Uses: Opioid receptor agonist; analgesic.

Technology Process of Codeine hydrochloride

There total 2 articles about Codeine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

codeine N-oxide hydrochloride → N-norcodeine hydrochloride (14648-14-7) + codeine hydrochloride (1422-07-7)

Guidance literature:

With iron(III) chloride hexahydrate; iron; In chloroform; isopropyl alcohol; at 20 ℃; for 36h;

DOI:10.1071/CH11320

Reference yield:

codeine (76-57-3) → N-norcodeine hydrochloride (14648-14-7) + codeine hydrochloride (1422-07-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / chloroform; isopropyl alcohol / 0.42 h / -5 °C

2: iron(III) chloride hexahydrate; iron / chloroform; isopropyl alcohol / 36 h / 20 °C

With iron(III) chloride hexahydrate; iron; 3-chloro-benzenecarboperoxoic acid; In chloroform; isopropyl alcohol;

DOI:10.1071/CH11320

Reference yield: 70.0%

codeine hydrochloride (1422-07-7) → 6β-chloro-4,5α-epoxy-3-methoxy-17-methyl-morphin-7-ene (467-08-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In benzene; Ambient temperature;

upstream raw materials:

codeine

Downstream raw materials:

6β-chloro-4,5α-epoxy-3-methoxy-17-methyl-morphin-7-ene

(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

codeinone

Oxycodone

Refernces