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Adrenorphin

From Wikipedia, the free encyclopedia

Adrenorphin
Names
IUPAC name
L-Tyrosylglycylglycyl-L-phenylalanyl-L-methionyl-L-arginyl-L-arginyl-L-valinamide
Identifiers
3D model (JSmol)
ChemSpider
  • 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 checkY
    Key: XJOQRTJDYAHKPY-YVWIMRNGSA-N checkY
  • 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
  • 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
Properties
C44H69N15O9S
Molar mass984.18 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Adrenorphin, also sometimes referred to asmetorphamide, is anendogenous,C-terminallyamidated,opioidoctapeptide (Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH2, YGGFMRRV-NH2) that is produced fromproteolyticcleavage ofproenkephalin A and is widely distributed throughout themammalianbrain.[1][2][3][4][5] It was named based on the fact that it was originally detected inhumanphaeochromocytomatumour derived from theadrenal medulla, and was subsequently found in normal human andbovine adrenal medulla as well.[1] Adrenorphin exhibitspotent opioid activity, acting as a balancedμ- andκ-opioid receptoragonist while having no effects onδ-opioid receptors.[2] It possessesanalgesic andrespiratory depressive properties.[6]

See also

[edit]

References

[edit]
  1. ^abMatsuo H, Miyata A, Mizuno K (1983). "Novel C-terminally amidated opioid peptide in human phaeochromocytoma tumour".Nature.305 (5936):721–723.Bibcode:1983Natur.305..721M.doi:10.1038/305721a0.PMID 6633641.S2CID 4320171.
  2. ^abWeber E, Esch FS, Böhlen P, Paterson S, Corbett AD, McKnight AT, 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):7362–7366.Bibcode:1983PNAS...80.7362W.doi:10.1073/pnas.80.23.7362.PMC 390055.PMID 6316361.
  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):892–898.doi:10.1016/0006-291X(84)91174-4.PMID 6477570.
  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):1030–1036.doi:10.1016/S0006-291X(84)80210-7.PMID 6732783.
  5. ^Miyata A, Mizuno K, Honzawa M, Tohyama M, Matsuo H (February 1985). "Adrenorphin immunoreactivity in rat brain".Neuropeptides.5 (4–6):517–520.doi:10.1016/0143-4179(85)90068-X.PMID 2860609.S2CID 11442343.
  6. ^Xu SF, Lu WX, Zhou KR, He XP, Niu SF, Xu WM, et al. (April 1985). "The analgesic and respiratory depressant actions of metorphamide in mice and rabbits".Neuropeptides.6 (2):121–131.doi:10.1016/0143-4179(85)90103-9.PMID 4000426.S2CID 7848759.
Hormones
Opioid peptides
Dynorphins
Endomorphins
Endorphins
Enkephalins
Others
Other
neuropeptides
Kinins
Neuromedins
Orexins
Other
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
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