548-08-3

Basic information

• Product Name: roemerine
• Synonyms: roemerine;(-)-N-Methylanonaine;(-)-Roemerine【alkaloid】;(6aR)-6-Methyl-1,2-(methylenedioxy)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline;[7aR,(-)]-6,7,7a,8-Tetrahydro-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline;Remerine【alkaloid】;Roemerine【alkaloid】;(-)-Remerine
• CAS NO: 548-08-3
• Molecular Formula: C₁₈H₁₇NO₂
• Molecular Weight: 279.337
• Mol File: 548-08-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 102-103℃
• Boiling Point: 424°Cat760mmHg
• Flash Point: 162.4°C
• Appearance: /
• Density: 1.269±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 2.13E-07mmHg at 25°C
• Refractive Index: 1.65
• PKA: 7.87±0.20(Predicted)
• CAS DataBase Reference: roemerine(CAS DataBase Reference)
• NIST Chemistry Reference: roemerine(548-08-3)
• EPA Substance Registry System: roemerine(548-08-3)

Safety Data

• Hazardous Substances Data: 548-08-3(Hazardous Substances Data)

Usage

Uses

Roemerine is an (-)-aporphine type of alkaloid which has been shown to possess significant antibacterial activity against Escheria Coli.

InChI:InChI=1/C18H17NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,9,14H,6-8,10H2,1H3/t14-/m1/s1

Synthetic route

formaldehyd (50-00-0) + formic acid (64-18-6) + anonaine (1862-41-5, 7241-00-1, 33116-39-1, 58846-21-2) → roemerine (548-08-3)

(+/-)-roemerine (2030-53-7, 15548-23-9) → roemerine (548-08-3)

Conditions	Yield
With L-Tartaric acid

formaldehyd (50-00-0) + anonaine (1862-41-5, 7241-00-1, 33116-39-1, 58846-21-2) → roemerine (548-08-3)

Conditions	Yield
With formic acid at 100℃;
With sodium tetrahydroborate

roemerine (548-08-3) → (4R,6aR)-4-hydroxyromerine (24191-98-8, 56688-64-3, 81445-54-7, 108267-40-9)

Conditions	Yield
With Clonostachys rogersoniana 828H2 In methanol; water at 28℃; for 168h; Microbiological reaction; stereospecific reaction;	97.4%

Upstream product

• 71524-02-2 (S)-7-methyl-11-(1-phenyl-1H-tetrazol-5-yloxy)-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline 
• 87201-31-8 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 87201-30-7 N-<-2-(3,4-methylenedioxyphenyl)ethyl>-2'-bromophenylacetamide 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 1862-41-5 anonaine 
• 2030-53-7 (+/-)-roemerine 
• 65981-49-9 (S)-11-methoxy-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline 
• 3466-56-6 (+)-mecambroline 
• 1093-07-8 (-)-mecambrine 

Downstream Products

• 36285-03-7 dehydroroemerine 
• 24191-98-8 Epi-steporphin 

Relevant articles and documents

Synthesis and evaluation of nuciferine and roemerine enantiomers as 5-HT2 and α1 receptor antagonists

In this study, the (S)-enantiomers of the aporphine alkaloids, nuciferine and roemerine, were prepared via a synthetic route involving catalytic asymmetric hydrogenation and both stereoisomers were evaluated in vitro for functional activity at human 5-HT2 and adrenergic α1 receptor subtypes using a transforming growth factor-α shedding assay. Both enantiomers of each of the compounds were found to act as antagonists at 5-HT2 and α1 receptors. (R)-roemerine was the most potent compound at 5-HT2A and 5-HT2C receptors (pKb = 7.8-7.9) with good selectivity compared to (S)-roemerine at these two receptors and compared to its activity at 5-HT2B, α1A, α1B and α1D receptors.

Alkaloids of Annonaceae: alkaloids of the bark of Cananga odorata Hook. f. and Thomson

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