アドレノルフィン

アドレノルフィン
	IUPAC名 L-tyrosylglycylglycyl-L-phenylalanyl-L-methionyl-N~5~-(diaminomethylidene)-L-ornithyl-N~5~-(diaminomethylidene)-D-ornithyl-L-valinamide
識別情報
CAS登録番号	88377-68-8
PubChem	122176
ChemSpider	108968
	SMILES O=C(N)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)Cc2ccccc2)CCSC)CCC/N=C(\N)N)CCC/N=C(\N)N)C(C)C;
	InChI InChI=1S/C44H69N15O9S/c1-25(2)36(37(46)63)59-41(67)31(12-8-19-52-44(49)50)57-39(65)30(11-7-18-51-43(47)48)56-40(66)32(17-20-69-3)58-42(68)33(22-26-9-5-4-6-10-26)55-35(62)24-53-34(61)23-54-38(64)29(45)21-27-13-15-28(60)16-14-27/h4-6,9-10,13-16,25,29-33,36,60H,7-8,11-12,17-24,45H2,1-3H3,(H2,46,63)(H,53,61)(H,54,64)(H,55,62)(H,56,66)(H,57,65)(H,58,68)(H,59,67)(H4,47,48,51)(H4,49,50,52)/t29-,30-,31+,32-,33-,36-/m0/s1 Key: XJOQRTJDYAHKPY-YVWIMRNGSA-N ; InChI=1S/C44H69N15O9S/c1-25(2)36(37(46)63)59-41(67)31(12-8-19-52-44(49)50)57-39(65)30(11-7-18-51-43(47)48)56-40(66)32(17-20-69-3)58-42(68)33(22-26-9-5-4-6-10-26)55-35(62)24-53-34(61)23-54-38(64)29(45)21-27-13-15-28(60)16-14-27/h4-6,9-10,13-16,25,29-33,36,60H,7-8,11-12,17-24,45H2,1-3H3,(H2,46,63)(H,53,61)(H,54,64)(H,55,62)(H,56,66)(H,57,65)(H,58,68)(H,59,67)(H4,47,48,51)(H4,49,50,52)/t29-,30-,31+,32-,33-,36-/m0/s1 Key: XJOQRTJDYAHKPY-YVWIMRNGBT; InChI=1/C44H69N15O9S/c1-25(2)36(37(46)63)59-41(67)31(12-8-19-52-44(49)50)57-39(65)30(11-7-18-51-43(47)48)56-40(66)32(17-20-69-3)58-42(68)33(22-26-9-5-4-6-10-26)55-35(62)24-53-34(61)23-54-38(64)29(45)21-27-13-15-28(60)16-14-27/h4-6,9-10,13-16,25,29-33,36,60H,7-8,11-12,17-24,45H2,1-3H3,(H2,46,63)(H,53,61)(H,54,64)(H,55,62)(H,56,66)(H,57,65)(H,58,68)(H,59,67)(H4,47,48,51)(H4,49,50,52)/t29-,30-,31+,32-,33-,36-/m0/s1 Key: XJOQRTJDYAHKPY-YVWIMRNGBT;
特性
化学式	C44H69N15O9S
モル質量	984.18 g/mol
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

アドレノルフィン(Adrenorphin)は、内生の、C末端アミド化オピオイドオクタペプチド(Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH₂)である。プロエンケファリンのタンパク質分解により生成し、哺乳類の脳に広く分布している^[1]^[2]^[3]^[4]^[5]。ヒトやウシの通常の脳にも存在するが、最初にヒトの副腎髄質(Adrenal medulla)の褐色細胞腫から検出されたということから名付けられた^[1]。アドレノルフィンは、μ-オピオイド受容体とκ-オピオイド受容体には作用するが、δ-オピオイド受容体には作用しない、強いオピオイド活性を示す^[2]。呼吸抑制や鎮痛の効果を持つ^[6]。

出典

^ ^a ^b Matsuo H, Miyata A, Mizuno K (1983). “Novel C-terminally amidated opioid peptide in human phaeochromocytoma tumour”. Nature 305 (5936): 721–3. doi:10.1038/305721a0. PMID 6633641.
^ ^a ^b Weber E, Esch FS, Böhlen P et al. (December 1983). “Metorphamide: isolation, structure, and biologic activity of an amidated opioid octapeptide from bovine brain”. Proceedings of the National Academy of Sciences of the United States of America 80 (23): 7362–6. doi:10.1073/pnas.80.23.7362. PMC 390055. PMID 6316361.
^ Sonders M, Barchas JD, Weber E (August 1984). “Regional distribution of metorphamide in rat and guinea pig brain”. Biochemical and Biophysical Research Communications 122 (3): 892–8. doi:10.1016/0006-291X(84)91174-4. PMID 6477570.
^ Miyata A, Mizuno K, Minamino N, Matsuo H (May 1984). “Regional distribution of adrenorphin in rat brain: comparative study with PH-8P”. Biochemical and Biophysical Research Communications 120 (3): 1030–6. doi:10.1016/S0006-291X(84)80210-7. PMID 6732783.
^ Miyata A, Mizuno K, Honzawa M, Tohyama M, Matsuo H (February 1985). “Adrenorphin immunoreactivity in rat brain”. Neuropeptides 5 (4–6): 517–20. doi:10.1016/0143-4179(85)90068-X. PMID 2860609.
^ Xu SF, Lu WX, Zhou KR et al. (April 1985). “The analgesic and respiratory depressant actions of metorphamide in mice and rabbits”. Neuropeptides 6 (2): 121–31. doi:10.1016/0143-4179(85)90103-9. PMID 4000426.

[pmid6633641-1] Matsuo H, Miyata A, Mizuno K (1983). “Novel C-terminally amidated opioid peptide in human phaeochromocytoma tumour”. Nature 305 (5936): 721–3. doi:10.1038/305721a0. PMID 6633641.

[pmid6316361-2] Weber E, Esch FS, Böhlen P et al. (December 1983). “Metorphamide: isolation, structure, and biologic activity of an amidated opioid octapeptide from bovine brain”. Proceedings of the National Academy of Sciences of the United States of America 80 (23): 7362–6. doi:10.1073/pnas.80.23.7362. PMC 390055. PMID 6316361.

[pmid6477570-3] Sonders M, Barchas JD, Weber E (August 1984). “Regional distribution of metorphamide in rat and guinea pig brain”. Biochemical and Biophysical Research Communications 122 (3): 892–8. doi:10.1016/0006-291X(84)91174-4. PMID 6477570.

[pmid6732783-4] Miyata A, Mizuno K, Minamino N, Matsuo H (May 1984). “Regional distribution of adrenorphin in rat brain: comparative study with PH-8P”. Biochemical and Biophysical Research Communications 120 (3): 1030–6. doi:10.1016/S0006-291X(84)80210-7. PMID 6732783.

[pmid2860609-5] Miyata A, Mizuno K, Honzawa M, Tohyama M, Matsuo H (February 1985). “Adrenorphin immunoreactivity in rat brain”. Neuropeptides 5 (4–6): 517–20. doi:10.1016/0143-4179(85)90068-X. PMID 2860609.

[pmid4000426-6] Xu SF, Lu WX, Zhou KR et al. (April 1985). “The analgesic and respiratory depressant actions of metorphamide in mice and rabbits”. Neuropeptides 6 (2): 121–31. doi:10.1016/0143-4179(85)90103-9. PMID 4000426.

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関連項目

出典