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Endomorphin

Endomorphin-1
Names
IUPAC name
(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
Other names
Tyr-Pro-Trp-Phe-NH2; L-Tyrosyl-L-prolyl-L-tryptophyl-L-phenylalaninamide
Identifiers
3D model (JSmol)
Abbreviations YPWF
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C34H38N6O5/c35-26(17-22-12-14-24(41)15-13-22)34(45)40-16-6-11-30(40)33(44)39-29(19-23-20-37-27-10-5-4-9-25(23)27)32(43)38-28(31(36)42)18-21-7-2-1-3-8-21/h1-5,7-10,12-15,20,26,28-30,37,41H,6,11,16-19,35H2,(H2,36,42)(H,38,43)(H,39,44)/t26-,28-,29-,30-/m0/s1
    Key: ZEXLJFNSKAHNFH-SYKYGTKKSA-N
  • C1C[C@H](N(C1)C(=O)[C@H](CC2=CC=C(C=C2)O)N)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@@H](CC5=CC=CC=C5)C(=O)N
Properties
C34H38N6O5
Molar mass 610.715 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Endomorphin-2
Names
IUPAC name
(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide
Other names
Tyr-Pro-Phe-Phe-NH2; L-Tyrosyl-L-prolyl-L-phenylalanyl-L-phenylalaninamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C32H37N5O5/c33-25(18-23-13-15-24(38)16-14-23)32(42)37-17-7-12-28(37)31(41)36-27(20-22-10-5-2-6-11-22)30(40)35-26(29(34)39)19-21-8-3-1-4-9-21/h1-6,8-11,13-16,25-28,38H,7,12,17-20,33H2,(H2,34,39)(H,35,40)(H,36,41)/t25-,26-,27-,28-/m0/s1
    Key: XIJHWXXXIMEHKW-LJWNLINESA-N
  • C1C[C@H](N(C1)C(=O)[C@H](CC2=CC=C(C=C2)O)N)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)N
Properties
C32H37N5O5
Molar mass 571.678 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Endomorphins are considered to be natural opioid neuropeptides central to pain relief.[1] The two known endomorphins, endomorphin-1 and endomorphin-2, are tetrapeptides, consisting of Tyr-Pro-Trp-Phe and Tyr-Pro-Phe-Phe amino acid sequences respectively.[2] These sequences fold into tertiary structures with high specificity and affinity for the μ-opioid receptor, binding it exclusively and strongly. Bound μ-opioid receptors typically induce inhibitory effects on neuronal activity.[3] Endomorphin-like immunoreactivity exists within the central and peripheral nervous systems, where endomorphin-1 appears to be concentrated in the brain and upper brainstem, and endomorphin-2 in the spinal cord and lower brainstem.[2] Because endomorphins activate the μ-opioid receptor, which is the target receptor of morphine and its derivatives, endomorphins possess significant potential as analgesics with reduced side effects and risk of addiction.[4]

  1. ^ Koob, George F. (2014). Drugs, Addiction, and the Brain. Academic Press. pp. 133–171. ISBN 978-0-12-386937-1.
  2. ^ a b Bodnar, Richard J (2018). "Endogenous Opiates and Behavior: 2016". Peptides. 101: 167–212. doi:10.1016/j.peptides.2018.01.011. PMID 29366859. S2CID 3542686.
  3. ^ Horvath, Gyöngyi (2000). "Endomorphin-1 and endomorphin-2: Pharmacology of the selective endogenous μ-opioid receptor agonists". Pharmacology & Therapeutics. 88 (3): 437–63. doi:10.1016/S0163-7258(00)00100-5. PMID 11337033.
  4. ^ Gu, Zheng-Hui; Wang, Bo; Kou, Zhen-Zhen; Bai, Yang; Chen, Tao; Dong, Yu-Lin; Li, Hui; Li, Yun-Qing (2017). "Endomorphins: Promising Endogenous Opioid Peptides for the Development of Novel Analgesics". Neurosignals. 25 (1): 98–116. doi:10.1159/000484909. PMID 29132133.

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