TRIMU 5

TRIMU-5 is a selective agonist of the μ2-opioid receptor and antagonist of the μ1-opioid receptor.[1][2] It produces analgesia in animals that differs from that of conventional μ-opioid receptor agonists but that can still be blocked by μ-opioid receptor antagonists.[1] TRIMU-5 can also block the analgesic effects of μ-opioid receptor agonists like morphine.[1] In addition to analgesia, TRIMU-5 inhibits gastrointestinal transit, a known effect of μ2-opioid receptor activation.[1]

TRIMU 5
Names
IUPAC name
L-tyrosyl-N-{[(3-methylbutyl)amino]acetyl}-D-alaninamide
Preferred IUPAC name
(2R)-2-Amino-3-(4-hydroxyphenyl)-N-[(2R)-1-{2-[(3-methylbutyl)amino]acetamido}-1-oxopropan-2-yl]propanamide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C19H30N4O4/c1-12(2)8-9-21-11-17(25)23-18(26)13(3)22-19(27)16(20)10-14-4-6-15(24)7-5-14/h4-7,12-13,16,21,24H,8-11,20H2,1-3H3,(H,22,27)(H,23,25,26)/t13-,16?/m1/s1 Y
    Key: QOGVSHVPIMZZRN-JBZHPUCOSA-N Y
  • InChI=1/C19H30N4O4/c1-12(2)8-9-21-11-17(25)23-18(26)13(3)22-19(27)16(20)10-14-4-6-15(24)7-5-14/h4-7,12-13,16,21,24H,8-11,20H2,1-3H3,(H,22,27)(H,23,25,26)/t13-,16?/m1/s1
    Key: QOGVSHVPIMZZRN-JBZHPUCOBN
SMILES
  • Oc1ccc(C[C@@H](N)C(=O)N[C@H](C)C(=O)NC(=O)CNCCC(C)C)cc1
Properties
Chemical formula
 C19H30N4O4
Molar mass 378.466
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

References
  1. Tive LA, Pick CG, Paul D, Roques BP, Gacel GA, Pasternak GW (June 1992). "Analgesic potency of TRIMU-5: a mixed mu 2 opioid receptor agonist/mu 1 opioid receptor antagonist". Eur J Pharmacol. 216 (2): 249–55. doi:10.1016/0014-2999(92)90367-d. PMID 1327812.
  2. Eisenberg RM (1994). "TRIMU-5, a mu 2-opioid receptor agonist, stimulates the hypothalamo-pituitary-adrenal axis". Pharmacol. Biochem. Behav. 47 (4): 943–6. doi:10.1016/0091-3057(94)90300-X. PMID 8029266. S2CID 54354971.


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