Title: Armepavine
CAS Registry Number: 524-20-9
CAS Name: 4-[[(1R)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]phenol
Additional Names: (-)-6,7-dimethoxy-1-p-hydroxybenzyl-2-methyl-1,2,3,4-tetrahydroisoquinoline
Molecular Formula: C19H23NO3
Molecular Weight: 313.39
Percent Composition: C 72.82%, H 7.40%, N 4.47%, O 15.32%
Literature References: Isoln from Papaver armeniacum (L.) DC., Papaveraceae: Konowalowa et al., Ber. 68, 2161 (1935); from Euonymus europaea L., Celastraceae: Bishay et al., J. Pharm. Pharmacol. 23 (Suppl), 233S (1971); from Rhamnus frangula L., Rhamnaceae: Pailer, Haslinger, Monatsh. Chem. 103, 1399 (1972). Structure: eidem, J. Gen. Chem. USSR 10, 641 (1940). Synthesis: Marion et al., J. Org. Chem. 15, 216 (1950); Gibson et al., J. Heterocycl. Chem. 3, 99 (1966). Resolution: Knabe, Horn, Arch. Pharm. 300, 547 (1967); Farber, Giacomazi, Chem. Ind. (London) 1968 (2), 57.
Properties: mp 149-150°. [a]D20 -117.6° (CHCl3) (Knabe); [a]D27 -103.2° (Farber).
Melting point: mp 149-150°
Optical Rotation: [a]D20 -117.6° (CHCl3) (Knabe); [a]D27 -103.2° (Farber)
Derivative Type: 10-Camphorsulfonate hydrate
Molecular Formula: C29H39NO7S.H2O
Molecular Weight: 563.70
Percent Composition: C 61.79%, H 7.33%, N 2.48%, O 22.71%, S 5.69%
Properties: mp 130°. [a]D20 -65° (MeOH).
Melting point: mp 130°
Optical Rotation: [a]D20 -65° (MeOH)
Derivative Type: dl-Form hydrate
Properties: Needles from acetone + ether; loses its water around 100°, then melts at 140°. Freely sol in alc, acetone, chloroform; slightly sol in ether. Almost insol in water.
Melting point: melts at 140°
Derivative Type: dl-Form hydrochloride
Molecular Formula: C19H23NO3.HCl
Molecular Weight: 349.85
Percent Composition: C 65.23%, H 6.91%, N 4.00%, O 13.72%, Cl 10.13%
Properties: Needles from alcohol + ether, mp 152°. Freely soluble in water and alc.
Melting point: mp 152°
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