Thebaine
Title: Thebaine
CAS Registry Number: 115-37-7
CAS Name: (5a)-6,7,8,14-Tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan
Additional Names: paramorphine
Molecular Formula: C19H21NO3
Molecular Weight: 311.37
Percent Composition: C 73.29%, H 6.80%, N 4.50%, O 15.42%
Literature References: From opium, which contains from 0.3-1.5% depending on its origin. Discussion of structure and bibliography: Small, Lutz, "Chemistry of the Opium Alkaloids" in U.S. Public Health Reports Suppl. No. 103 (Washington, 1932); Small, Browning, J. Org. Chem. 3, 618 (1938); Cherbuliez, Araqui, Helv. Chim. Acta 26, 2251 (1943); Ghosh, Robinson, J. Chem. Soc. 1944, 506; K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954) p 184 sqq. Config: Kalvoda et al., Helv. Chim. Acta 38, 1847 (1955). Syntheses: Rapoport et al., J. Am. Chem. Soc. 89, 1942 (1967); Schwartz, Mami, ibid. 97, 1239 (1975); Barber, Rapoport, J. Med. Chem. 18, 1074 (1975). Absorption spectrum: Csokán, Z. Anal. Chem. 124, 344 (1942). Toxicity data: Eddy, J. Pharmacol. Exp. Ther. 66, 182 (1939).
Properties: Orthorhombic, rectangular plates by sublimation at 170-180° under atmospheric pressure and a 1 mm distance. mp 193° (rapid heating). [a]D15 -219° (p = 2 in alc); [a]D23 -230° (p = 5 in chloroform). pK at 15° = 6.05. pH of satd water soln 7.6. One gram dissolves in 1460 ml water at 15° [Kolthoff, Biochem. Z. 162, 336 (1925)], in about 15 ml hot alcohol or 13 ml chloroform, about 200 ml ether, 25 ml benzene, 12 ml pyridine; not very sol in petr ether.
Melting point: mp 193° (rapid heating)
pKa: pK at 15° = 6.05
Optical Rotation: [a]D15 -219° (p = 2 in alc); [a]D23 -230° (p = 5 in chloroform)
 
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C19H21NO3.HCl.H2O
Molecular Weight: 365.85
Percent Composition: C 62.38%, H 6.61%, N 3.83%, O 17.49%, Cl 9.69%
Properties: Orthorhombic prisms from alcohol, [a]D23 -164° (p = 2). Sol in about 12 parts water, in alcohol; pH of 0.05 molar soln 4.95. LD50 s.c. in rabbits: 14 mg/kg (Eddy).
Optical Rotation: [a]D23 -164° (p = 2)
Toxicity data: LD50 s.c. in rabbits: 14 mg/kg (Eddy)
 
Derivative Type: Oxalate hexahydrate
Molecular Formula: 2C19H21NO3.C2H2O4.6H2O
Molecular Weight: 820.88
Percent Composition: C 58.53%, H 6.88%, N 3.41%, O 31.18%
Properties: Prisms, sol in about 10 parts water, in alcohol. Almost insol in ether.
 
Derivative Type: Binoxalate monohydrate
Molecular Formula: C19H21NO3.C2H2O4.H2O
Molecular Weight: 419.43
Percent Composition: C 60.14%, H 6.01%, N 3.34%, O 30.52%
Properties: Prisms, sol in 45 parts water.
 
Derivative Type: Bitartrate monohydrate
Molecular Formula: C19H21NO3.C4H6O6.H2O
Molecular Weight: 479.48
Percent Composition: C 57.61%, H 6.10%, N 2.92%, O 33.37%
Properties: Prisms, sol in 130 parts water, quite sol in hot water, hot alcohol.
 
Derivative Type: Salicylate
Molecular Formula: C19H21NO3.C7H6O3
Molecular Weight: 449.50
Percent Composition: C 69.47%, H 6.05%, N 3.12%, O 21.36%
Properties: Crystals, sol in 750 parts water.
 
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.

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