Adrenorfin

Adrenorfin
	L-tyrosylglycylglycyl-L-phenylalanyl-L-methionyl-N~5~-(diaminomethylidene)-L-ornithyl-N~5~-(diaminomethylidene)-D-ornithyl-L-valinamide
Identifikacija
CAS registarski broj	88377-68-8
PubChem	122176
ChemSpider	108968
Jmol-3D slike	Slika 1
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 ; Kod: 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; Kod: 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; Kod: XJOQRTJDYAHKPY-YVWIMRNGBT
Svojstva
Molekulska formula	C44H69N15O9S
Molarna masa	984,18 g/mol
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Adrenorfin (metorfamid) je endogeni, C-terminalno amidisani, opioidni oktapeptid (Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH₂). On nastaje proteolitičim presecanjem proenkefalina A. Adrenorfin je široko rasprostranjen u mozgu sisara.^[4]^[5]^[6]^[7]^[8]

Dobio je ime po činjenici da je originalno nađen u humanom feohromocitomnom tumoru izvedenom iz srži nadbubrežne žlezde. Naknadno je utvrđeno da je isto tako prisutan u normalnoj humanoj i goveđoj adrenalnoj meduli.^[4] Adrenorfin ima potentno opioidno dejstvo. On deluje kao balansirani agonist μ- i κ-opioidnog receptora, a nema efekta na δ-opioidne receptore.^[5] On ispoljava analgetičke i respiratorno depresantske efekte.^[9]

Povezano

Opioidni peptidi

Literatura

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ ^4,0 ^4,1 Matsuo H, Miyata A, Mizuno K (1983). „Novel C-terminally amidated opioid peptide in human phaeochromocytoma tumour”. Nature 305 (5936): 721–3. PMID 6633641.
↑ ^5,0 ^5,1 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. 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. 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. PMID 4000426.

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[pmid6633641-4] 4,0 ^4,1 Matsuo H, Miyata A, Mizuno K (1983). „Novel C-terminally amidated opioid peptide in human phaeochromocytoma tumour”. Nature 305 (5936): 721–3. PMID 6633641.

[pmid6316361-5] 5,0 ^5,1 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. PMC 390055. PMID 6316361.

[pmid6477570-6] 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.

[pmid6732783-7] 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.

[pmid2860609-8] Miyata A, Mizuno K, Honzawa M, Tohyama M, Matsuo H (February 1985). „Adrenorphin immunoreactivity in rat brain”. Neuropeptides 5 (4-6): 517–20. PMID 2860609.

[pmid4000426-9] 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. PMID 4000426.

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