1936-18-1

Basic information

• Product Name: salutaridine
• Synonyms: salutaridine;5,6,8,14-Tetradehydro-4-hydroxy-3,6-dimethoxy-17-methylmorphinan-7-one
• CAS NO: 1936-18-1
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.37434
• Mol File: 1936-18-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 197-198°
• Boiling Point: 532.5°Cat760mmHg
• Flash Point: 275.8°C
• Appearance: /
• Density: 1.33g/cm³
• Refractive Index: 1.645
• CAS DataBase Reference: salutaridine(CAS DataBase Reference)
• NIST Chemistry Reference: salutaridine(1936-18-1)
• EPA Substance Registry System: salutaridine(1936-18-1)

Safety Data

• Hazardous Substances Data: 1936-18-1(Hazardous Substances Data)

Usage

Description

An alkaloid obtained from Croton salutaris, this base has been postulated as an intermediate compound in the biosynthesis of the morphine alkaloids. It yields colourless rods when crystallized from AcOEt and has [α]D + 111 ° (c 1.69, EtOH). The ultraviolet spectrum in EtOH has two absorption maxima at 240 and 277 mJl. Two methoxyl groups, a phenolic hydroxyl group and a methylimino group are present, the base furnishing an O-acetate, m.p. 171°C; [α]D + 120° (c 1.25, EtOH). More recently, it has been discovered in Croton balsamifera Jacq. and Papaver orientale.

Uses

Salutaridine is one of the biosynthetic precursors of morphine (M652290), a principle alkaloid of opium.

References

Barton et al., J. Chem. Soc., 2423 (1965) Battersby, Brown., Chem. Commun., 170 (1966) Chambers, Haynes, Stuart., ibid, 449 (1966) Mass spectra: Wheeler, Kinstle, Rinehart.,J. Amer. Chem. Soc., 89,4494 (1967)

InChI:InChI=1/C19H21NO4/c1-20-7-6-19-10-16(24-3)14(21)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9-10,13,22H,6-8H2,1-3H3/t13-,19+/m1/s1

Upstream product

• 485-19-8 (R)-reticuline 
• 2611-69-0 O⁴-acetylsalutaridine 
• 104779-63-7 (S)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-4,4-dimethoxy-cyclohex-2-enylmethyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 104779-68-2 4,4-Dimethoxy-3-oxo-cyclohexanecarboxylic acid ethyl ester 
• 104779-67-1 (3-Bromomethyl-6,6-dimethoxy-cyclohex-1-enyloxy)-tert-butyl-dimethyl-silane 
• 104779-66-0 [1-(6,7-Dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-((1S,2S)-2-phenyl-2-trimethylsilanyloxy-1-trimethylsilanyloxymethyl-ethyl)-amine 
• 27669-33-6 O⁶-demethylsalutaridine 
• 75820-93-8 O⁴-acetyl-O⁶-demethylsalutaridine 
• 75820-95-0 O^4,6-diacetyl-O⁶-demethylsalutaridine 

Downstream Products

• 115-37-7 thebaine 

Relevant articles and documents

Formation of the morphine precursor salutaridine is catalyzed by a cytochrome P-450 enzyme in mammalian liver

A highly regio- and stereoselective microsomal-bound cytochrome P-450 NADPH dependent enzyme has been discovered in pig liver which is responsible for the intramolecular phenol oxidative coupling of (R)-reticuline to salutaridine, thus giving rise to the morphine skeleton in mammals.

Rat CYP2D2, not 2D1, is functionally conserved with human CYP2D6 in endogenous morphine formation

The assumption that CYP2D1 is the corresponding rat cytochrome to human CYP2D6 has been revisited using recombinant proteins in direct enzyme assays. CYP2D1 and 2D2 were incubated with known CYP2D6 substrates, the three morphine precursors thebaine, codeine and (R)-reticuline. Mass spectrometric analysis showed that rat CYP2D2, not 2D1, catalyzed the 3-O-demethylation reaction of thebaine and codeine. In addition, CYP2D2 incubated with (R)-reticuline generated four products corytuberine, pallidine, salutaridine and isoboldine while rat CYP2D1 was completely inactive. This intramolecular phenol-coupling reaction follows the same mechanism as observed for CYP2D6. Michaelis-Menten kinetic parameters revealed high catalytic efficiencies for rat CYP2D2. These findings suggest a critical evaluation of other commonly accepted, however untested, CYP2D1 substrates.

Totalsynthese von rac-Salutaridin und Sinoacutin ((-)-Salutaridin), ein neuer Weg zum Morphingeruest

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