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▣ 천연물에서 분리된 개별유효성분 레코드 등록정보 |
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성 분 명 |
Thebaine((-)-form) |
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다른이름들 |
Paramorphine
Codeinone methyl enol ether
6,7,8,14-Tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan |
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함유 천연물 |
Papaver somniferum L.[양귀비(Yang-gwi-bi)](앵속각(罌粟殼)) |
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분 자 식 |
C19H21NO3 |
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화학족 분류 |
알칼로이드(alkaloid); |
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분 자 량 |
311.384 |
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녹 는 점 |
193°C MeOH |
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생리학적효과 |
Cholinesterase inhibitor. CNS stimulant. Narcotic showing higher narcotic activity but weaker analgesic activity than morphine. More toxic than morphine. Causes histamine release from tissues.. Toxicity: LD50 (mus, ipr) 20 mg/kg. Hydrochloride monohydrate;LD50 s.c. in rabbits: 14 mg/kg (Eddy). LD50(mus, scu) 117mg/kg. |
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굴 절 율 |
[α]16 D = -221° (C 0.35,MeOH) |
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UV_CHART |
(λmax, nm) (MeOH):285(3.91) |
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HNMR_CHART |
(CDCl3/CD3OD,60 MHz) δ:6.76(H1), 6.63(H2), 5.10(H7), 5.62(H8), 5.30(H5), 2.46(NMe), 3.87(MeO), 3.62(MeO) |
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CNMR_CHART |
(CDCl3,15.09 MHz) δ: 119.1, 112.9, 142.7, 144.6, 89.0, 152.3, 95.8, 111.3, 60.7, 29.5, 127.6, 133.1, 46.0, 132.3, 37.0, 46.0, 42.3, 56.2, 54.7 |
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MASS_CHART |
M+= 311, m/z= 311(100), 310, 282, 268, 255, 254, 253, 174 |
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참고문헌 |
· JD. Phillipson et al., Phytochemistry, 15, 1297, 1976(pmr)
· K. Tori et al., Tetrahedron Lett., 2853, 1975(cmr)
· AI. Gray et al., Planta Med., 41, 2, 1, 1981(uv,ms)
· S. Okuda et al., Chem. Pharm. Bull., 12, 104, 1964(pmr)
· E. Brochmann-Hanssen et al., J. Pharm. Sci., 53, 1549, 1964
· DHR. Barton et al., J. Chem. Soc., 2423, 1965
· H. Rapoport et al., J. Am. Chem. Soc., 89, 1942, 1967
· DMS. Wheeler et al., J. Am. Chem. Soc., 89, 4494, 1967
· T. Kametani et al., J. Chem. Soc.(C), 2030, 1969
· E. Brochmann-Hanssen et al., J. Org. Chem., 37, 1881, 1972
· RB. Barber et al., J. Med. Chem., 18, 1074, 1975
· DD. Weller et al., J. Med. Chem., 19, 1171, 1976
· HG. Theuns et al., J. Chem. Soc. Perkin 1, 1701, 1984
· KC. Rice, Chem. Biol. Isoquinoline Alkaloids, Int. Symp., Phytochem. Soc. Eur., Abstr. Pap., 191, 1985 |
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