552-70-5

Basic information

• Product Name: 9-Methyl-9-azabicyclo[3.3.1]nonan-3-one
• Synonyms: PSEUDO-PELLETIERINE;9-methyl-9-azabicyclo(3.3.1)nonan-3-on;9-methyl-9-azabicyclo(3.3.1)nonan-3-one;granatan-3-one;granatonine;pseudopelletierin;pseudopunicine;psi-pelletierine
• CAS NO: 552-70-5
• Molecular Formula: C₉H₁₅NO
• Molecular Weight: 153.22
• EINECS: 209-021-1
• Product Categories: Amines and Anilines;Carbonyl Compounds;Heterocyclic Compounds;Enzyme substrates;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C9;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 552-70-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 63-65°C
• Boiling Point: bp 246°
• Flash Point: 95.9 °C
• Appearance: colorless (yellows on exposure)
• Density: 1.0010
• Vapor Pressure: 0.0267mmHg at 25°C
• Refractive Index: 1.4760
• Storage Temp.: 2-8°C
• Solubility: Methanol (Sparingly), Water
• PKA: 8.99±0.20(Predicted)
• Merck: 13,8011
• BRN: 1525218
• CAS DataBase Reference: 9-Methyl-9-azabicyclo[3.3.1]nonan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Methyl-9-azabicyclo[3.3.1]nonan-3-one(552-70-5)
• EPA Substance Registry System: 9-Methyl-9-azabicyclo[3.3.1]nonan-3-one(552-70-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: CL5593500
• Hazardous Substances Data: 552-70-5(Hazardous Substances Data)

Usage

Chemical Properties

Tan Solid

Uses

Different sources of media describe the Uses of 552-70-5 differently. You can refer to the following data:
1. It was found in the root bark of Punica granatum
2. It was found in the root bark of Punica granatum L., Punicaceae. Used as a enzyme substrate.

Definition

ChEBI: An azabicycloalkane alkaloid that is 9-azabicyclo[3.3.1]nonane substituted by a methyl group at position 9 and an oxo group at position 3. It is found in pomegranate trees.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 3416, 1951 DOI: 10.1021/ja01151a123

InChI:InChI=1/C9H15NO/c1-10-7-3-2-4-8(10)6-9(11)5-7/h7-8H,2-6H2,1H3/t7-,8+

Upstream product

• 542-05-2 acetonedicarboxylic acid 
• 111-30-8 Glutaraldehyde 
• 74-89-5 methylamine 
• 18747-42-7 N-methylpelletierine 
• 32752-52-6 1-(N-methyl)-1,5-pentanediamine 
• 6376-00-7 exo-9-methyl-9-azabicyclo[3.3.1]nonan-3-ol 
• 7732-18-5 water 
• 593-51-1 methylamine hydrochloride 
• 6164-62-1 9-methyl-9-azabicyclo[3.3.1]nonan-3-one hydrochloride 
• 6635-57-0 1,5-pentanedioxime 
• 110-86-1 pyridine 
• 5057-98-7 cis-1,2-cyclopentanediol 
• 130894-62-1 1,5-Bis-benzenesulfonyl-3-methylene-cyclooctane 
• 93728-32-6 1,5-Diphenylsulfon-pentan 

Downstream Products

• 196611-36-6 N-(5-Chloro-2-methoxy-phenyl)-N'-((1R,3R,5S)-9-methyl-9-aza-bicyclo[3.3.1]non-3-yl)-ethane-1,2-diamine 
• 6376-00-7 exo-9-methyl-9-azabicyclo[3.3.1]nonan-3-ol 
• 2038-40-6 (3-endo)-9-methyl-9-azabicyclo[3.3.1]nonan-3-ol 
• 491-25-8 9-methyl-9-aza-bicyclo[3.3.1]nonane 
• 112658-72-7 N,N'-diethyl-N-(9-methyl-9-aza-bicyclo[3.3.1]non-3endo-yl)-N'-phenyl-ethylenediamine 
• 112300-57-9 N-[2-(N-ethyl-anilino)-ethyl]-N-(9-methyl-9-aza-bicyclo[3.3.1]non-3endo-yl)-formamide 
• 112841-48-2 N-[2-(N-ethyl-anilino)-ethyl]-N-(9-methyl-9-aza-bicyclo[3.3.1]non-3endo-yl)-acetamide 
• 72761-60-5 9-azabicyclo<3.3.1>nonan-3-one hydrochloride 
• 76272-41-8 endo-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine 
• 76272-56-5 exo-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine 
• 135906-03-5 C₉H₁₈N₂*ClH 

Relevant articles and documents

Monocarbonyl Analogs of Curcumin based on the pseudopelletierine scaffold: Synthesis and anti-inflammatory activity

Curcumin (CUR) is a natural compound that exhibits anti-inflammatory, anti-bacterial, and other biological properties. However, its application as an effective drug is problematic due to its poor oral bioavailability, solubility in water, and poor absorption from the gastrointestinal tract. The aim of this work is to synthesize monocarbonyl analogs of CUR based on the 9-methyl-9-azabicyclo[3.2.1]nonan-3-one (pseudopelletierine, granatanone) scaffold to improve its bioavailability. Granatane is a homologue of tropane, whose structure is present in numerous naturally occurring alkaloids, e.g., l-cocaine and l-scopolamine. In this study, ten new pseudopelletierine-derived monocarbonyl analogs of CUR were successfully synthesized and characterized by spectral methods and X-ray crystallography. Additionally, in vitro test of the cytotoxicity and anti-inflammatory properties of the synthesized compounds were performed.

Toward biophysical probes for the 5-HT3 receptor: Structure-activity relationship study of granisetron derivatives

This report describes the synthesis and biological characterization of novel granisetron derivatives that are antagonists of the human serotonin (5-HT3A) receptor. Some of these substituted granisetron derivatives showed low nanomolar binding affinity and allowed the identification of positions on the granisetron core that might be used as attachment points for biophysical tags. A BODIPY fluorophore was appended to one such position and specifically bound to 5-HT3A receptors in mammalian cells.

BICYCLIC FIVE-MEMBERED HETEROARYL DERIVATIVES AND THEIR USE AS RENIN INHIBITORS

The invention relates to novel five-membered heteroaryl derivatives and the use thereof as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions comprising one or more of those compounds and especially their use as inhibitors of renin.