Noroxymorphone

Base Information

• Chemical Name: Noroxymorphone
• CAS No.: 33522-95-1
• Molecular Formula: C16H17NO4
• Molecular Weight: 287.315
• European Community (EC) Number: 251-561-5
• UNII: 9NZ7111A9O
• DSSTox Substance ID: DTXSID80955145
• Nikkaji Number: J291.131K
• Wikipedia: Noroxymorphone
• Wikidata: Q25102255
• NCI Thesaurus Code: C87364
• Mol file: 33522-95-1.mol

Synonyms:noroxymorphone

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Chemical Property of Noroxymorphone

Chemical Property:

• Vapor Pressure: 5.05E-13mmHg at 25°C
• Melting Point: >265°C (dec.)
• Refractive Index: 1.722
• Boiling Point: 552.1 °C at 760 mmHg
• PKA: 9.20±0.40(Predicted)
• Flash Point: 287.7 °C
• PSA: 78.79000
• Density: 1.54 g/cm³
• LogP: 0.73180
• Storage Temp.: Controlled Substance, -20°C Freezer
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 287.11575802
• Heavy Atom Count: 21
• Complexity: 511

Purity/Quality:

Safty Information:

• Pictogram(s): T,F
• Hazard Codes: T,F
• Statements: 10-23/24/25-39/23/24/25-11
• Safety Statements: 36/37-45-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2(C3CC4=C5C2(CCN3)C(C1=O)OC5=C(C=C4)O)O
• Isomeric SMILES: C1C[C@]2([C@H]3CC4=C5[C@@]2(CCN3)[C@H](C1=O)OC5=C(C=C4)O)O
• Description: Noroxymorphone (Item No. 15903) is an analytical reference standard that is structurally categorized as an opioid. It is an active metabolite of oxycodone , noroxycodone (Item Nos. 15902 | 20407), and oxymorphone that can be detected in plasma and urine. Noroxymorphone is also an immediate precursor in the synthesis of several opioids, including naltrexone (Item Nos. 15520 | ISO60192) and naloxone (Item Nos. 15594 | ISO60191). Noroxymorphone is regulated as a Schedule II compound in the United States. This product is intended for research and forensic applications.
• Uses: A metabolite of Naloxone and Naltrexone

Technology Process of Noroxymorphone

There total 58 articles about Noroxymorphone 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: 88.0%

14-acetylnoroxymorphone hydrochloride (144333-31-3) → noroxymorphone (33522-95-1)

Guidance literature:

With sulfuric acid; at 100 - 102 ℃; for 5h;

DOI:10.1016/S0040-4020(01)80016-8

Reference yield: 83.0%

Naloxone (465-65-6) → noroxymorphone (33522-95-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; In dichloromethane; at 38 ℃; for 16h; Inert atmosphere;

DOI:10.1007/s10571-020-00867-6

Reference yield: 82.0%

(5aR,8aS,11aR,11bS)-2-acetoxy-5,5a,9,10-tetrahydro-6,11b-ethano-7Hfuro[2',3',4',5':4,5]phenanthro[9,8a-d]oxazol-11(11aH)-one (1407592-43-1) → noroxymorphone (33522-95-1)

Guidance literature:

With ammonia; acetic acid; at 20 - 50 ℃; for 18h; pH=9; Product distribution / selectivity;

upstream raw materials:

C₁₉H₂₁NO₆

N-(1-chloroethoxycarbonyl)-3-(^tbutyldimethylsilyl)-14-acetylnoroxymorphone

14-acetylnoroxymorphone hydrochloride

(4R,4aS,7aR,12bS)-9-((tert-butyldimethylsilyl)oxy)-4a-hydroxy-3-methyl-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

Downstream raw materials:

Naltrexone

Naloxone

7,8-didehydro-4,5α-epoxymorphinan-6-keto-3,14-diol

4,5α-epoxy-3,14-dihydroxy-17-phenethyl-morphinan-6-one

Refernces

• 1、 Machara, Ales,Endoma-Arias, Mary Ann A.,Císa?ová, Ivana,Cox, D. Phillip,Hudlicky, Tomas. "Direct Synthesis of Noroxymorphone from Thebaine: Unusual CeIV Oxidation of a Methoxydiene-Iron Complex to an Enone-γ-Nitrate". . p. 1500 - 1503. Retrieved 2016.
• 2、 Gutmann, Bernhard,Cantillo, David,Weigl, Ulrich,Cox, D. Phillip,Kappe, C. Oliver. "Design and Development of Pd-Catalyzed Aerobic N-Demethylation Strategies for the Synthesis of Noroxymorphone in Continuous Flow Mode". . p. 914 - 927. Retrieved 2017.
• 3、 Machara, Ale?,Endoma-Arias, Mary Ann A.,Císa?ova, Ivana,Cox, D. Phillip,Hudlicky, Tomá?. "Synthesis of Nororipavine and Noroxymorphone via N- and O-Demethylation of Iron Tricarbonyl Complex of Thebaine". . p. 1803 - 1813. Retrieved 2016.
• 4、 K?teles, István,Mazák, Károly,Tóth, Gerg?,T?z, Boglárka,Hosztafi, Sándor. "Synthesis of Potential Haptens with Morphine Skeleton and Determination of Protonation Constants". . . Retrieved 2020/09/17.
• 5、 -. "PROCESS FOR OBTAINING 3,14-DIACETYLOXYMORPHONE FROM ORIPAVINE". Page/Page column 44; 45. . Retrieved 2018/01/17.