111555-53-4

Basic information

• Product Name: Naltrindol
• Synonyms: Naltrindol;naltrindole;17-Cyclopropylmethyl-6,7-dehydro-4,5-epoxy-3,14-dihydroxy-6,7,2',3'-indolomorphinan;4,8-Methanobenzofuro(2,3-A)pyrido(4,3-B)carbazole-1,8A(9H)-diol, 7-(cyclopropylmethyl)-5,6,7,8,14,14B-hexahydro-, (4bs,8R,8as,14br)-;4,8-Methanobenzofuro(2,3-A)pyrido(4,3-B)carbazole-1,8A(9H)-diol, 7-(cyclopropylmethyl)-5,6,7,8,14,14B-hexahydro-, (8R-(4bs*,8alpha,8abeta,14bbeta))-
• CAS NO: 111555-53-4
• Molecular Formula: C₂₆H₂₆N₂O₃
• Molecular Weight: 414.502
• Mol File: 111555-53-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 647.2°Cat760mmHg
• Flash Point: 345.2°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 1.23E-17mmHg at 25°C
• Refractive Index: 1.803
• CAS DataBase Reference: Naltrindol(CAS DataBase Reference)
• NIST Chemistry Reference: Naltrindol(111555-53-4)
• EPA Substance Registry System: Naltrindol(111555-53-4)

Safety Data

• Hazardous Substances Data: 111555-53-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C26H26N2O3/c29-19-8-7-15-11-20-26(30)12-17-16-3-1-2-4-18(16)27-22(17)24-25(26,21(15)23(19)31-24)9-10-28(20)13-14-5-6-14/h1-4,7-8,14,20,24,27,29-30H,5-6,9-13H2/t20-,24+,25+,26-/m1/s1

Upstream product

• 100-63-0 phenylhydrazine 
• 16676-29-2 naltrexone Hydrochloride 
• 59-88-1 phenylhydrazine hydrochloride 
• 16590-41-3 Naltrexone 
• 126580-44-7 3-O-Methylnaltrindole 

Downstream Products

• 73232-52-7 methylnaltrexone bromide 
• 221103-42-0 17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-1'-(2-fluoroethyl)-6,7-2',3'-indolomorphinan 
• 948906-06-7 17-cyclopropylmethyl-6,7-didehydro-4,5-epoxy-3-benzyloxy-14-hydroxy-6,7,2',3'-[1'-(p-fluorobenzyl)]-indolomorphinan 
• 346601-12-5 3-O-triphenylmethylnaltrindole 
• 221103-41-9 17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-(p-tosyloxy)-14-hydroxy-6,7-2',3'-indolomorphinan 
• 161532-22-5 17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3-benzyloxy-14-hydroxy-6,7-2',3'-indolomorphinan 

Relevant articles and documents

Solid-phase synthesis of naltrindole derivatives using Fischer indole synthesis based on one-pot release and cyclization methodology

(Matrix presented) We describe a new approach for the solid-phase synthesis of indoles 1 that involves a one-pot release and cyclization reaction of a solid-supported hydrazone through a Wang-type linker. Using this solid-phase methodology, we accomplishe

Fischer indole synthesis in water: Simple, efficient preparation of naltrindole, naltriben and analogs

Naltrindole, naltrindole analogs and the benzofuran congener naltriben have been prepared by Fischer syntheses using mildly acidic, purely aqueous conditions. The preparation of naltrindole and several analogs was accomplished under almost neutral conditions using just the hydrochloride salts of naltrexone and various electron-rich and electron-poor phenylhydrazines in boiling water. The products were obtained by simple filtration in good to excellent yields and with high purities in the majority of cases. The route is suited to gram-scale synthesis, does not require the use of organic solvents, minimizes the use of corrosive acids, and is simple, efficient and environmentally friendly. Naltriben was prepared efficiently from the hydrochloride salts of naltrexone and O-phenylhydroxylamine but more forcing conditions, 6.0 N HCl, were required. A limitation to the method is the failure of Fischer cyclization between naltrexone and nitro-substituted phenylhydrazines under aqueous conditions.

Methods of o-demethylation and n-deprotection

The present invention provides a method for N-deprotecting an opioid compound, a method for N-deprotecting and O-demethylating an opioid compound, a method for O-demethylating an opioid compound, and a method for O-demethylating a nonpeptidic delta agonist compound or an opioid compound having a tertiary amide with no significant reaction at amide groups.