Adrenorphin

Last updated

Adrenorphin
Adrenorphin slim.svg
Names
IUPAC name
L-Tyrosylglycylglycyl-L-phenylalanyl-L-methionyl-L-arginyl-L-arginyl-L-valinamide
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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 Yes check.svgY
    Key: XJOQRTJDYAHKPY-YVWIMRNGSA-N Yes check.svgY
  • 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 mass 984.18 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Adrenorphin, also sometimes referred to as metorphamide, is an endogenous, C-terminally amidated, opioid octapeptide (Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH2, YGGFMRRV-NH2) that is produced from proteolytic cleavage of proenkephalin A and is widely distributed throughout the mammalian brain. [1] [2] [3] [4] [5] It was named based on the fact that it was originally detected in human phaeochromocytoma tumour derived from the adrenal medulla, and was subsequently found in normal human and bovine adrenal medulla as well. [1] Adrenorphin exhibits potent opioid activity, acting as a balanced μ- and κ-opioid receptor agonist while having no effects on δ-opioid receptors. [2] It possesses analgesic and respiratory depressive properties. [6]

See also

Related Research Articles

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<span class="mw-page-title-main">Amidorphin</span> Chemical compound

Amidorphin is an endogenous, C-terminally amidated, opioid peptide generated as a cleavage product of proenkephalin A in some mammalian species; in humans and most other species, the peptide is 1 residue longer and is not amidated. Amidorphin is widely distributed in the mammalian brain, with particularly high concentrations found in the striatum, and outside of the brain in adrenal medulla and posterior pituitary. The 26-residue peptide named amidorphin is found in several species including bovine, sheep, and pig. Humans and commonly studied lab animals produce a 27-residue peptide that does not have an amidated C-terminal residue; this is due to the absence of a Gly in the precursor sequence and replacement with Ala, which is not a substrate for the amidating enzyme. The properties of the 27-residue peptide are presumably similar to those of amidorphin, although this has not been adequately tested.

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<span class="mw-page-title-main">Proenkephalin</span> Protein-coding gene in the species Homo sapiens

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<span class="mw-page-title-main">Hemorphin-4</span> Endogenous opioid peptide

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<span class="mw-page-title-main">Tonazocine</span> Chemical compound

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Deltorphin I, also known as [D-Ala2]deltorphin I or deltorphin C, is a naturally occurring, exogenous opioid heptapeptide and hence, exorphin, with the amino acid sequence Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2. While not known to be endogenous to humans or other mammals, deltorphin I, along with the other deltorphins and the dermorphins, is produced naturally in the skin of species of Phyllomedusa, a genus of frogs native to South and Central America. Deltorphin possesses very high affinity and selectivity as an agonist for the δ-opioid receptor, and on account of its unusually high blood-brain-barrier penetration rate, produces centrally-mediated analgesic effects in animals even when administered peripherally.

<span class="mw-page-title-main">Zenazocine</span> Opioid analgesic

Zenazocine is an opioid analgesic of the benzomorphan family which made it to phase II clinical trials before development was ultimately halted and it was never marketed. It acts as a partial agonist of the μ- and δ-opioid receptors, with less intrinsic activity at the former receptor and more at the latter receptor, and produces antinociceptive effects in animal studies.

References

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  2. 1 2 Weber 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.
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