EXP-561

EXP-561
識別
CAS號	10206-89-0
PubChem	27696
性質
化學式	C14H19N
摩爾質量	201.31 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

EXP-561，即4-苯基雙環[2.2.2]辛-1-胺，是一種有機化合物，化學式為C₁₄H₁₉N。它可以被3-氯過氧苯甲酸氧化為1-硝基-4-苯基雙環[2.2.2]辛烷。^[1]在碳酸鉀的存在下，它可以和1-溴-2-甲氧基乙烷在乙腈中加熱反應，得到N-(2-甲氧基乙基)-4-苯基雙環[2.2.2]辛-1-胺。^[2]

1960年代，它被杜邦公司發展^[3] 並被提名為一種抗抑鬱藥，不過失敗了^[4]，也沒有上市過。^[5]^[6]^[7]^[8]

參考文獻

^ William Adcock, Gaik B. Kok. Polar substituent effects on fluorine-19 chemical shifts of aryl and vinyl fluorides: a fluorine-19 nuclear magnetic resonance study of some 1,1-difluoro-2-(4-substituted-bicyclo[2.2.2]oct-1-yl)ethenes. The Journal of Organic Chemistry. 1985-04, 50 (7): 1079–1087 [2021-05-18]. ISSN 0022-3263. doi:10.1021/jo00207a033 （英語）.
^ Kick, Ellen K.; Smallheer, Joanne M.; Shaw, Scott A.; Vokits, Benjamin P.; Dilger, Andrew K.; Clark, Charles G.; Valente, Meriah Neissel; Jusuf, Sutjano; Wurtz, Nicholas R. Triazolopyridines as inhibitors of myeloperoxidase and/or eosinophil peroxidase and their preparation. 2017. WO 2017161145 A1.
^ US Patent 3308160 - PHENYLBICYCLO[Z.Z.Z]OCTANE-L-AMINES AND SALTS THEREOF
^ INTERNATIONAL REVIEW NEUROBIOLOGY, Volume 12 Page 160
^ Maj J, Skuza G, Sowińska H, Nowak G. Pharmacological properties of EXP 561, a potential antidepressant drug. Journal of Neural Transmission. 1987, 70 (1–2): 81–97. PMID 2822850. S2CID 23469131. doi:10.1007/BF01252511.
^ Lehmann HE, Ban TA, Debow SL. A clinical-pharmacological study with EXP 561. Current Therapeutic Research, Clinical and Experimental. June 1967, 9 (6): 306–8. PMID 4963065.
^ Gershon S, Hekimian LJ, Floyd A. Non-correlation of preclinical-clinical evaluation of a prosposed anti-depressant 4-phenyl-bicyclo(2,2,2)octan-1-amine hydrochloride monohydrate (EXP 561). Arzneimittel-Forschung. February 1968, 18 (2): 243–5. PMID 5695389.
^ Ross SB, Kelder D. Inhibition of 3H-dopamine accumulation in reserpinized and normal rat striatum. Acta Pharmacologica et Toxicologica. May 1979, 44 (5): 329–35. PMID 474143. doi:10.1111/j.1600-0773.1979.tb02339.x.

[1] William Adcock, Gaik B. Kok. Polar substituent effects on fluorine-19 chemical shifts of aryl and vinyl fluorides: a fluorine-19 nuclear magnetic resonance study of some 1,1-difluoro-2-(4-substituted-bicyclo[2.2.2]oct-1-yl)ethenes. The Journal of Organic Chemistry. 1985-04, 50 (7): 1079–1087 [2021-05-18]. ISSN 0022-3263. doi:10.1021/jo00207a033 （英語）.

[2] Kick, Ellen K.; Smallheer, Joanne M.; Shaw, Scott A.; Vokits, Benjamin P.; Dilger, Andrew K.; Clark, Charles G.; Valente, Meriah Neissel; Jusuf, Sutjano; Wurtz, Nicholas R. Triazolopyridines as inhibitors of myeloperoxidase and/or eosinophil peroxidase and their preparation. 2017. WO 2017161145 A1.

[3] US Patent 3308160 - PHENYLBICYCLO[Z.Z.Z]OCTANE-L-AMINES AND SALTS THEREOF

[4] INTERNATIONAL REVIEW NEUROBIOLOGY, Volume 12 Page 160

[pmid2822850-5] Maj J, Skuza G, Sowińska H, Nowak G. Pharmacological properties of EXP 561, a potential antidepressant drug. Journal of Neural Transmission. 1987, 70 (1–2): 81–97. PMID 2822850. S2CID 23469131. doi:10.1007/BF01252511.

[pmid4963065-6] Lehmann HE, Ban TA, Debow SL. A clinical-pharmacological study with EXP 561. Current Therapeutic Research, Clinical and Experimental. June 1967, 9 (6): 306–8. PMID 4963065.

[pmid5695389-7] Gershon S, Hekimian LJ, Floyd A. Non-correlation of preclinical-clinical evaluation of a prosposed anti-depressant 4-phenyl-bicyclo(2,2,2)octan-1-amine hydrochloride monohydrate (EXP 561). Arzneimittel-Forschung. February 1968, 18 (2): 243–5. PMID 5695389.

[pmid474143-8] Ross SB, Kelder D. Inhibition of 3H-dopamine accumulation in reserpinized and normal rat striatum. Acta Pharmacologica et Toxicologica. May 1979, 44 (5): 329–35. PMID 474143. doi:10.1111/j.1600-0773.1979.tb02339.x.

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