N-Cyclopropylmethylnoroxycodone

Base Information

• Chemical Name: N-Cyclopropylmethylnoroxycodone
• CAS No.: 16617-07-5
• Molecular Formula: C21H25 N O4
• Molecular Weight: 355.434
• DSSTox Substance ID: DTXSID70937172
• Nikkaji Number: J448.966G
• Wikidata: Q82913382
• Pharos Ligand ID: U1LGRFC62Q9F
• ChEMBL ID: CHEMBL387016
• Mol file: 16617-07-5.mol

Synonyms:N-Cyclopropylmethylnoroxycodone;3-O-Methylnaltrexone;16617-07-5;Naltrexone-3-methyl ether;O3-Methyl-(-)-naltrexone;Naltrexone 3-Methyl Ether;CHEMBL387016;Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-14-hydroxy-3-methoxy-, (5alpha)-;Methoxynaltrexone,3;Morphinan-6-one, 17-(cyclopropylmethyl)-4,5alpha-epoy-14-hydroxy-3-methoxy-;(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a-hydroxy-9-methoxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;N-Cyclopropylmethyl noroxycodone;SCHEMBL15241475;DTXSID70937172;DSMNGWOUQMYTJH-MBPVOVBZSA-N;BDBM50195664;LS-183742;A937608;17-(cyclopropylmethyl)-14-hydroxy-3-methoxy-4,5-epoxymorphinan-6-one;(1S,5R,13R,17S)-4-(cyclopropylmethyl)-17-hydroxy-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one;(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a-hydroxy-9-methoxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

Chemical Property of N-Cyclopropylmethylnoroxycodone

Chemical Property:

• Vapor Pressure: 1.24E-12mmHg at 25°C
• Boiling Point: 543.2°Cat760mmHg
• Flash Point: 282.3°C
• PSA: 59.00000
• Density: 1.38g/cm³
• LogP: 1.76630
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 355.17835828
• Heavy Atom Count: 26
• Complexity: 636

Purity/Quality:

99.0% Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2C3=C(CC4C5(C3(CCN4CC6CC6)C(O2)C(=O)CC5)O)C=C1
• Isomeric SMILES: COC1=C2C3=C(C[C@@H]4[C@]5([C@]3(CCN4CC6CC6)[C@@H](O2)C(=O)CC5)O)C=C1
• Uses: A potent antagonist of the antinociceptive effects of heroin.

Technology Process of N-Cyclopropylmethylnoroxycodone

There total 35 articles about N-Cyclopropylmethylnoroxycodone 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: 100.0%

Naltrexone (16590-41-3) + methyl iodide (74-88-4) → naltrexone methyl ether (16617-07-5)

Guidance literature:

With potassium carbonate; In dichloromethane; for 18h;

Reference yield: 100.0%

C22H21BrF3NO7S → naltrexone methyl ether (16617-07-5)

Guidance literature:

With hydrogen; palladium(II) hydroxide; triethylamine; In methanol; ethyl acetate; at 23 ℃; under 760.051 Torr;

DOI:10.1039/c8sc03748e

Reference yield: 93.0%

naltrexone Hydrochloride (16676-29-2) + methyl iodide (74-88-4) → naltrexone methyl ether (16617-07-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 7h; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.152714

upstream raw materials:

noroxycodone

cyclopropylcarbinyl bromide

diazomethane

Naltrexone

Downstream raw materials:

C₂₈H₃₂N₂O₄

C₁₇H₂₁NO₃

C₂₅H₂₇NO₆S

(4bR,7S,8aS,9R)-7-(2-(benzyloxy)ethyl)-11-(cyclopropylmethyl)-8a-hydroxy-3-methoxy-8,8a9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one

Refernces

• 1、 Nagase, Hiroshi,Yamamoto, Naoshi,Yata, Masahiro,Ohrui, Sayaka,Okada, Takahiro,Saitoh, Tsuyoshi,Kutsumura, Noriki,Nagumo, Yasuyuki,Irukayama-Tomobe, Yoko,Ishikawa, Yukiko,Ogawa, Yasuhiro,Hirayama, Shigeto,Kuroda, Daisuke,Watanabe, Yurie,Gouda, Hiroaki,Yanagisawa, Masashi. "Design and Synthesis of Potent and Highly Selective Orexin 1 Receptor Antagonists with a Morphinan Skeleton and Their Pharmacologies". . p. 1018 - 1040. Retrieved 2017.
• 2、 Hino, Tsubasa,Kutsumura, Noriki,Saitoh, Tsuyoshi,Yamamoto, Naoshi,Nagumo, Yasuyuki,Mogi, Yuzo,Watanabe, Yoshikazu,Nagase, Hiroshi. "Novel Baeyer–Villiger-type oxidation of 4,5-epoxymorphinan derivatives". . . Retrieved 2021.
• 3、 Iwamatsu, Chiharu,Hayakawa, Daichi,Kono, Tomomi,Honjo, Ayaka,Ishizaki, Saki,Hirayama, Shigeto,Gouda, Hiroaki,Fujii, Hideaki. "Effects of N-substituents on the functional activities of naltrindole derivatives for the δ opioid receptor: Synthesis and evaluation of sulfonamide derivatives". . . Retrieved 2020.
• 4、 Larson, Dennis L.,Jones, Robert M.,Hjorth, Siv A.,Schwartz, Thue W.,Portoghese, Philip S.. "Binding of norbinaltorphimine (norBNI) congeners to wild-type and mutant mu and kappa opioid receptors: Molecular recognition loci for the pharmacophore and address components of kappa antagonists". . p. 1573 - 1576. Retrieved 2000.
• 5、 -. "NONCRUSHABLE PILL FORMULATIIONS". Paragraph 00362-00364. . Retrieved 2018/07/29.