1-碘吗啡

1-碘吗啡
	IUPAC名; (4R,4aR,7S,7aR,12bS)-11-Iodo-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline-7,9-diol
识别
CAS号	64739-76-0
PubChem	10993301
ChemSpider	9168496
SMILES	O[C@H]1\C=C/[C@H]4[C@H]2Cc5c3c(O[C@@H]1[C@]34CCN2C)c(O)cc5I;
InChI	1/C17H18INO3/c1-19-5-4-17-9-2-3-12(20)16(17)22-15-13(21)7-10(18)8(14(15)17)6-11(9)19/h2-3,7,9,11-12,16,20-21H,4-6H2,1H3/t9-,11+,12-,16-,17-/m0/s1;
InChIKey	YFXOJQFZAJTGHD-GLWLLPOHBC
性质
化学式	C17H18INO3
摩尔质量	411.23 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

1-碘吗啡（英语：1-Iodomorphine）是由吗啡碳骨架1位卤化而成的半合成麻醉性镇痛药。^[1]^[2]^[3]1890年至1930年期间，德国、奥地利/奥匈帝国、英国和美国首先合成了卤化吗啡衍生物。1945年以后，这种药物的使用有所增加，用于下述研究。它是一种研究性化学物质，通常在需要时在实验室中制备。

与类似的2-碘吗啡以及二氢吗啡、二氢可待因、海洛因的碘化类似物以及该系列的氟化、氯化和溴化类似物一起，这种变化可能不会显着影响药物的活性^{[來源請求]}，但1- 和2-碘吗啡用于药理学、神经学、代谢和内分泌研究，因为它允许用碘-131或碘-129标记吗啡。^[4]此类研究对于发现人类、哺乳动物、鸟类和一些爬行动物、两栖动物、鱼类、昆虫和节肢动物的中枢神经系统、周围神经系统和其他组织中的阿片受体非常重要。

参考资料

^ Liebman, A. A.; Malarek, D. H.; Blount, J. F.; Nelson, N. R.; Delaney, C. M. Preparation and crystal structure of 6-acetyl-1-iodocodeine. The Journal of Organic Chemistry. 1978, 43 (4): 737–739. doi:10.1021/jo00398a049.
^ Seltzman, H. H.; Roche, M. J.; Laudeman, C. P.; Wyrick, C. D.; Carroll, F. I. Protection of the allylic alcohol double bond from catalytic reduction in the preparation of [1-3H]morphine and [1-3H]codeine. Journal of Labelled Compounds and Radiopharmaceuticals. 1998, 41 (9): 811–821. doi:10.1002/(SICI)1099-1344(1998090)41:9<811::AID-JLCR132>3.0.CO;2-3.
^ Wentland, M. P.; Duan, W.; Cohen, D. J.; Bidlack, J. M. Selective Protection and Functionalization of Morphine: Synthesis and Opioid Receptor Binding Properties of 3-Amino-3-desoxymorphine Derivatives. Journal of Medicinal Chemistry. 2000, 43 (19): 3558–3565. PMID 11000010. doi:10.1021/jm000119i.
^ Tafani, J. A.; Lazorthes, Y.; Danet, B.; Verdie, J. C.; Esquerre, J. P.; Simon, J.; Guiraud, R. Human brain and spinal cord scan after intracerebroventricular administration of iodine-123 morphine. International Journal of Radiation Applications and Instrumentation. Part B, Nuclear Medicine and Biology. 1989, 16 (5): 505–509. PMID 2807956. doi:10.1016/0883-2897(89)90064-0.

[1] Liebman, A. A.; Malarek, D. H.; Blount, J. F.; Nelson, N. R.; Delaney, C. M. Preparation and crystal structure of 6-acetyl-1-iodocodeine. The Journal of Organic Chemistry. 1978, 43 (4): 737–739. doi:10.1021/jo00398a049.

[2] Seltzman, H. H.; Roche, M. J.; Laudeman, C. P.; Wyrick, C. D.; Carroll, F. I. Protection of the allylic alcohol double bond from catalytic reduction in the preparation of [1-3H]morphine and [1-3H]codeine. Journal of Labelled Compounds and Radiopharmaceuticals. 1998, 41 (9): 811–821. doi:10.1002/(SICI)1099-1344(1998090)41:9<811::AID-JLCR132>3.0.CO;2-3.

[3] Wentland, M. P.; Duan, W.; Cohen, D. J.; Bidlack, J. M. Selective Protection and Functionalization of Morphine: Synthesis and Opioid Receptor Binding Properties of 3-Amino-3-desoxymorphine Derivatives. Journal of Medicinal Chemistry. 2000, 43 (19): 3558–3565. PMID 11000010. doi:10.1021/jm000119i.

[4] Tafani, J. A.; Lazorthes, Y.; Danet, B.; Verdie, J. C.; Esquerre, J. P.; Simon, J.; Guiraud, R. Human brain and spinal cord scan after intracerebroventricular administration of iodine-123 morphine. International Journal of Radiation Applications and Instrumentation. Part B, Nuclear Medicine and Biology. 1989, 16 (5): 505–509. PMID 2807956. doi:10.1016/0883-2897(89)90064-0.

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参考资料

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