6883-44-9

Basic information

• Product Name: Egenine
• Synonyms: Egenine;(+)-Decumbensine;(6R,8S)-6,8-Dihydro-6-[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8-ol;(6R)-6,8-Dihydro-6α-[[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin]-5-yl]furo[3,4-e]-1,3-benzodioxol-8α-ol
• CAS NO: 6883-44-9
• Molecular Formula: C20H19NO6
• Molecular Weight: 369.37
• Product Categories: Miscellaneous Natural Products
• Mol File: 6883-44-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 511.3 °C at 760 mmHg
• Flash Point: 263 °C
• Appearance: /
• Density: 1.478
• PKA: 11.87±0.40(Predicted)
• CAS DataBase Reference: Egenine(CAS DataBase Reference)
• NIST Chemistry Reference: Egenine(6883-44-9)
• EPA Substance Registry System: Egenine(6883-44-9)

Safety Data

• Hazardous Substances Data: 6883-44-9(Hazardous Substances Data)

Usage

General Description

Egenine is a chemical compound that falls under the category of alkaloids and is found in various plants, particularly in the genus Cephaelis. It is a potent stimulant that acts on the central nervous system and has been traditionally used by indigenous communities in South America for its psychoactive and medicinal properties. Egenine has been studied for its potential therapeutic effects, including as an anti-inflammatory and analgesic agent. However, it also has toxic effects and can be harmful if consumed in large doses. Research on egenine is ongoing to better understand its pharmacological properties and potential medical applications.

Upstream product

• 131589-17-8 -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-1,3-dioxolo<4,5-g>isoquinoline-5-methyl L-tartrate 
• 131681-57-7 -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo<4,5-g>isoquinoline-5-methanol 
• 68-12-2 N,N-dimethyl-formamide 
• 131589-16-7 (1S)-trans-1,5,6,10b-tetrahydro-1-(1,3-benzodioxol-5-yl)-3H-oxazolo<4,3-a>1,3-dioxolo<4,5-g>isoquinolin-3-one 
• 131079-60-2 -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-1,3-dioxolo<4,5-g>isoquinoline-5-methanol 
• 131589-14-5 -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-6-(2,2-dimethyl-1-oxopropyl)-1,3-dioxolo<4,5-g>isoquinoline-5-methanol 
• 131589-15-6 -(1,3-benzodioxol-5-yl)(5,6,7,8-tetrahydro-1,3-dioxolo<4,5-g>isoquinolin-5-yl)methyl 2,2-dimethylpropanoic acid ester 
• 131681-58-8 -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo<4,5-g>isoquinoline-5-methanol 
• 56083-00-2 (+/-)-bicuculline 
• 1077-75-4 (4-hydroxymethyl-benzo[1,3]dioxol-5-yl)methanol 
• 75267-17-3 5-Formyl-benzo[1,3]dioxole-4-carboxylic acid ethyl ester 
• 494-55-3 N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 52315-62-5 3,4-(methylenedioxy)phthalaldehyde 
• 131589-16-7 (1S)-cis-1,5,6,10b-tetrahydro-1-(1,3-benzodioxol-5-yl)-3H-oxazolo<4,3-a>1,3-dioxolo<4,5-g>isoquinolin-3-one 

Relevant articles and documents

Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines

A concise diastereotioselective strategy for the synthesis of noscapine, bicuculline, and egenine (1a-c), as well as capnoidine and corytensine (2a,b), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to iminium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler-Napieralsky reaction from amine 11. The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 (3).

Lewis acid complexed heteroatom carbanions; a convenient route to α-hydroxybenzyltetrahydroisoquinoline alkaloids

Treatment of the BF3 complex of 6,7-methylenedioxy-2-methyltetrahydroisoquinoline (2) with secbutyllithium followed by addition of piperonal gave α-hydroxybenzyltetrahydroisoquinolines 3a and 3b, while addition of 3,4-methylenedioxyphthaldehyde (4) afforded alkaloids (±)corytensine (5) and (±) egenine (6) along with isomeric hemiacetals 7 and 8.