An endogenous neuropeptide and μ-opioid receptor agonist
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Endomorphin 1 (trifluoroacetate salt)

Item No. 23280

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-tyrosyl-L-prolyl-L-tryptophyl-L-phenylalaninamide, trifluoroacetate salt
Synonyms
  • Tyr-Pro-Trp-Phe-NH2
Molecular Formula
C34H38N6O5 • XCF3COOH
Formula Weight
610.7
Purity
≥95%
Formulation (Request formulation change)
A lyophilized powder
Solubility(Learn about Variance in Solubility)
Formic Acid: 1 mg/ml
SMILES
O=C([C@H]1N(C([C@@H](N)CC2=CC=C(O)C=C2)=O)CCC1)N[C@H](C(N[C@@H](CC3=CC=CC=C3)C(N)=O)=O)CC4=CNC5=C4C=CC=C5.FC(F)(C(O)=O)F
InChi Code
InChI=1S/C34H38N6O5.C2HF3O2/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;3-2(4,5)1(6)7/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);(H,6,7)/t26-,28-,29-,30-;/m0./s1
InChi Key
HHLSEYUJSLAGOQ-YAOJAVRNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $96

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    Product Description

    Endomorphin 1 is an endogenous neuropeptide and μ-opioid receptor agonist (Ki = 0.36 nM) that has analgesic, positive reinforcing, and gastrointestinal properties.1,2 It is found in the brain and, to a lesser extent, in the spinal cord.3 It is selective for μ- over δ- and κ-opioid receptors (Ki = 1,506 and 5,428 nM, respectively).1 Endomorphin 1 also binds to mouse brain membranes and rat recombinant μ-opioid receptors expressed in CHO cells (Kis = 0.94 and 0.66 nM, respectively).2 It inhibits cAMP accumulation induced by forskolin in CHO cells expressing rat recombinant μ-opioid receptors and in SH-SY5Y human neuroblastoma cells (IC50s = 9.33 and 19.1 nM, respectively).4 In mice, endomorphin 1 increases analgesia in a radiant heat tail-flick assay following intracerebroventricular or intrathecal administration (ED50s = 4.75 and 0.726 μg, respectively) and induces conditioned place preference when administered intracerebroventricularly at a dose of 10 μg.2,5 Endomorphin 1 (12 μg, i.c.v.) also decreases gastrointestinal transit time in mice.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zadina, J.E., Hackler, L., Ge, L.J., et al. A potent and selective endogenous agonist for the µ-opiate receptor. Nature 386(6624), 499-502 (1997).

    2. Goldberg, I.E., Rossi, G.C., Letchworth, S.R., et al. Pharmacological characterization of endomorphin-1 and endomorphin-2 in mouse brain. J. Pharmacol. Exp. Ther. 286(2), 1007-1013 (1998).

    3. Martin-Schild, S., Gerall, A.A., Kastin, A.J., et al. Differential distribution of endomorphin 1- and endomorphin 2-like immunoreactivities in the CNS of the rodent. J. Comp. Neurol. 405(4), 450-471 (1999).

    4. Harrison, C., McNulty, S., Smart, D., et al. The effects of endomorphin-1 and endomorphin-2 in CHO cells expressing recombinant μ-opioid receptors and SH-SY5Y cells. Br. J. Pharmacol. 128(2), 472-478 (1999).

    5. Wu, H.-e., MacDougall, R.S., Clithero, A.D., et al. Opposite conditioned place preference responses to endomorphin-1 and endomorphin-2 in the mouse. Neurosci. Lett. 365(3), 157-161 (2004).