Endomorphin-1

Endomorphin-1 (EM-1) (amino acid sequence Tyr-Pro-Trp-Phe-NH₂) is an endogenous opioid peptide and one of the two endomorphins.[1] It is a high affinity, highly selective agonist of the μ-opioid receptor, and along with endomorphin-2 (EM-2), has been proposed to be the actual endogenous ligand of the μ-receptor.[1][2][3][4] EM-1 produces analgesia in animals and is equipotent with morphine in this regard.[3] The gene encoding for EM-1 has not yet been identified,[4] and it has been suggested that endomorphins could be synthesized by an enzymatic, non-ribosomal mechanism.[5]

Endomorphin-1

Names
IUPAC name L-Tyrosyl-L-prolyl-L-tryptophyl-L-phenylalaninamide
Identifiers
CAS Number	189388-22-5
3D model (JSmol)	Interactive image
ChemSpider	4470614
IUPHAR/BPS	1623
PubChem CID	5311080e
CompTox Dashboard (EPA)	DTXSID10415505
InChI 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 InChI=1/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-SYKYGTKKBN
SMILES c1ccc(cc1)C[C@@H](C(=O)N)NC(=O)[C@H](Cc2c[nH]c3c2cccc3)NC(=O)[C@@H]4CCCN4C(=O)[C@H](Cc5ccc(cc5)O)N
Properties
Chemical formula	C34H38N6O5
Molar mass	610.703 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

• β-Endorphin

References

1. Bodnar RJ, Commons KG, Pfaff DW (3 April 2002). Central Neural States Relating Sex and Pain. JHU Press. pp. 67–. ISBN 978-0-8018-6827-6.
2. Krammer HJ, Singer MV (31 May 2000). Neurogastroenterology - From the Basics to the Clinics. Springer Science & Business Media. pp. 76–. ISBN 978-0-7923-8757-2.
3. Brain S, Moore PK (1999). Pain and Neurogenic Inflammation. Springer Science & Business Media. pp. 28–. ISBN 978-3-7643-5875-4.
4. Offermanns S, Rosenthal W (14 August 2008). Encyclopedia of Molecular Pharmacology. Springer Science & Business Media. pp. 904–. ISBN 978-3-540-38916-3.
5. Terskiy A, Wannemacher KM, Yadav PN, Tsai M, Tian B, Howells RD (November 2007). "Search of the human proteome for endomorphin-1 and endomorphin-2 precursor proteins". Life Sciences. 81 (23–24): 1593–601. doi:10.1016/j.lfs.2007.09.025. PMC 2144908. PMID 17964607.