141392-30-5

Basic information

• Product Name: 6-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan
• Synonyms: 6-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan
• CAS NO: 141392-30-5
• Molecular Formula: C20H24 I N O3
• Molecular Weight: 0
• Mol File: 141392-30-5.mol

Chemical Properties

• Boiling Point: 571.2°Cat760mmHg
• Flash Point: 299.3°C
• Appearance: /
• Density: 1.78g/cm³
• Vapor Pressure: 6.89E-14mmHg at 25°C
• Refractive Index: 1.742
• CAS DataBase Reference: 6-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan(CAS DataBase Reference)
• NIST Chemistry Reference: 6-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan(141392-30-5)
• EPA Substance Registry System: 6-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan(141392-30-5)

Safety Data

• Hazardous Substances Data: 141392-30-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H24INO3/c21-13-5-6-20(24)15-9-12-3-4-14(23)17-16(12)19(20,18(13)25-17)7-8-22(15)10-11-1-2-11/h3-4,11,13,15,18,23-24H,1-2,5-10H2/t13-,15+,18-,19-,20+/m0/s1

Upstream product

• 141392-25-8 3-acetoxy-6β-<<(trifluoromethyl)sulfonyl>oxy>-14-hydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan 
• 59888-59-4 3-acetoxy-6β,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan 
• 16590-41-3 Naltrexone 
• 49625-89-0 β-naltrexol 
• 141392-27-0 3-acetoxy-6α-iodo-14-hydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan 

Relevant articles and documents

Probes for Narcotic Receptor Mediated Phenomena. 18. Epimeric 6α- and 6β-Iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinans as Potential Ligands for Opioid Receptor Single Photon Emission Computed Tomography: Synthesis, Evaluation, and Radiochemistry of...

The epimeric 6β- and 6α-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinans (1, ioxy) and (2, epioxy), respectively, were each synthesized in five steps starting with naltrexone.The configuration of the 6-iodo group of 1 was unequivocally determined to be β-based on single crystal X-ray analysis of its precursor 3-acetoxy-6β-iodo-14-hydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan (10).Both 1 and 2 as well as their corresponding 3-O-acetates 10 and 11 were found to readily cross the blood-brain barrier and completely reverse the analgesic effects of a 10 mg/kg intraperitoneal dose of morphine sulfate as determined by the paw withdrawal latency test.Compounds 1 and 2 were found to bind with high affinity to μ, δ and κ receptors in vitro.In general, 1 and 2 exhibited higher affinity for μ and κ receptors than naltrexone while the 6β-iodo epimer 1 (ioxy) was more potent than its epimer 2.In a comparison of the 6β-halogen substituent on binding affinity across opioid receptor subtypes, it was generally found that I>Br>F.On the basis of the results of in vitro and in vivo testing, 1 was selected as a target for radioiodination and evaluation as a potential single photon emission computed tomography imaging agent for opioid receptors.Carrier-free -1 was synthesized in near quantitative yield by the sequence of reaction of excess 3-acetoxy-6α-oxy>-14-hydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan (8) with anhydrous Na125I in dry acetonitrile for 90 min at 76 deg C followed by deacetylation of the product with 1:1 aqueous ammonia/acetonitrile at 25 deg C.The potential of -1 as an in vivo imaging agent for opioid receptors is evaluated and discussed.

Radiolabeled N-substituted-6-iodo-3,14-dihydroxy-4,5α-epoxymorphinans

The present invention is directed to radiolabeled N-substituted-6-iodo-3,14-dihydroxy-4,5α-epoxymorphinans, intermediates for producing the same, and a process for the preparation and methods of detecting opioid receptors.The radioimaging agent of the present invention has the following formula: STR1 wherein I is selected from the group consisting of 123 I and 125 I; and where R is alkyl, cycloalkylloweralkyl or allyl.