2169-44-0

Basic information

• Product Name: 4H-Dibenzo(de,g)quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6 -methyl-, (S)-
• Synonyms: 4H-Dibenzo(de,g)quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6 -methyl-, (S)-;(+)-6-Methyl-1,2,10-trimethoxy-5,6,6aα,7-tetrahydro-4H-dibenzo[de,g]quinoline-9-ol;(+)-N-Methyllaurotetamine;(6aS)-5,6,6a,7-Tetrahydro-1,2,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-9-ol;Lauroscholtzine;Methyllaurotetanine;Rogersine;Boldine 2-methyl ether
• CAS NO: 2169-44-0
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.44
• Mol File: 2169-44-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 102.5°C
• Boiling Point: 477.03°C (rough estimate)
• Flash Point: 259.9°C
• Appearance: /
• Density: 1.2064 (rough estimate)
• Vapor Pressure: 7.29E-11mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• CAS DataBase Reference: 4H-Dibenzo(de,g)quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6 -methyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Dibenzo(de,g)quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6 -methyl-, (S)-(2169-44-0)
• EPA Substance Registry System: 4H-Dibenzo(de,g)quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6 -methyl-, (S)-(2169-44-0)

Safety Data

• Hazardous Substances Data: 2169-44-0(Hazardous Substances Data)

Usage

Description

This alkaloid, identified as the N-methyl derivative of laurotetanine (q. v.), has been isolated from Escholtzia californica Cham., Phylica fengerialla and P. rogersii Pillans. The base is known in two modifications; as an amorphous powder and a colourless crystals from MeOH containing 0.5 mole of solvent, identical with rogersine (q.v.). The alkaloid has [α]D + 1110 (c 0.86, MeOH) and the ultraviolet spectrum in EtOH has absorption maxima at 219, 282 and 304 rn[J.; while that in alkaline solution (0.05 N/NaOH) has absorption maxima at 223 and 329 mil. The alkaloid yields a crystalline hydriodide, m.p. 245°C; the methiodide, m.p. 199-2000 C and the Q-ethyl (-)-tartrate, m.p. 206-7°C (dec.) giving a methiodide, m.p. 213° C.

References

Arndt, Baarschers., J. Chern. Soc., 2244 (1964) Manske, Shin., Can. J. Chern., 43,2180 (1965) Baarschers, Arndt., Tetrahedron, 21,2155 (1965) Pachler, Arndt, Baarschers., ibid, 21,2159 (1965)

InChI:InChI=1/C20H23NO4/c1-21-6-5-11-9-17(24-3)20(25-4)19-13-10-16(23-2)15(22)8-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3/t14-/m0/s1

Upstream product

• 67-56-1 methanol 
• 476-70-0 boldine 
• 4684-22-4 (-)-roemerialinone 

Relevant articles and documents

Semisynthetic studies on and biological evaluation of N-methyllaurotetanine analogues as ligands for 5-HT receptors

N-Methyllaurotetanine (1) has been reported to display good affinity for the 5-HT1A receptor, but no structure-affinity studies have been performed to date. The commercially available alkaloid boldine (2) was used as the starting material for s