A neuropeptide and δ- and µ-opioid receptor agonist
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Met-Enkephalin (trifluoroacetate salt)

Item No. 23284

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-tyrosylglycylglycyl-L-phenylalanyl-L-methionine, trifluoroacetate salt
Synonyms
  • [Met5]-Enkephalin
  • Methionine-Enkephalin
Molecular Formula
C27H35N5O7S • XCF3COOH
Formula Weight
573.7
Purity
≥95%
Formulation (Request formulation change)
A lyophilized powder
Solubility(Learn about Variance in Solubility)
Water: 1 mg/ml
SMILES
OC1=CC=C(C[C@H](N)C(NCC(NCC(N[C@H](C(N[C@H](C(O)=O)CCSC)=O)CC2=CC=CC=C2)=O)=O)=O)C=C1.FC(F)(C(O)=O)F
InChi Code
InChI=1S/C27H35N5O7S.C2HF3O2/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18;3-2(4,5)1(6)7/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39);(H,6,7)/t20-,21-,22-;/m0./s1
InChi Key
MFACXJYAPTVWQF-SGIIKHNDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $72

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    Product Description

    Met-Enkephalin is an endogenous neuropeptide involved in nociception and an agonist of δ- and µ-opioid receptors (Kis = 0.65 and 1.7 nM, respectively).1,2 It is selective for δ- and µ- over κ-opioid receptors (Ki = >1,000 nM).2 Met-Enkephalin is a cleavage product of proenkephalin, which is found primarily in the adrenal medulla and the CNS.3 Met-Enkephalin is found in the brain, primarily in the globus pallidus, nucleus accumbens, and substantia nigra, the brainstem, and the spinal cord as well as in the peripheral nervous system.3,4 Met-Enkephalin has antinociceptive effects in mouse models of acute pain, including tail pressure, hot plate tail-flick, and acetic acid-induced writhing tests (ED50s = 170, 140, and 88 nmol/animal, respectively).5 Levels of Met-enkephalin are increased at the site of inflammation in a complete Freund’s adjuvant mouse model of chronic inflammatory pain.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hughes, J., Smith, T.W., Kosterlitz, H.W., et al. Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature 258(5536), 577-580 (1975).

    2. Raynor, K., Kong, H., Chen, Y., et al. Pharmacological characterization of the cloned κ-, δ-, and μ-opioid receptors. Mol. Pharm. 45(2), 330-334 (1994).

    3. Roques, B.P., Noble, F., and Fournié-Zaluski, M.-C. Endrogenous opioid peptides and analgesia. Opioids in pain control: Basic and clinical aspects 22-25 (1999).

    4. Emson, P.C., Arregui, A., Clement-Jones, V., et al. Regional distribution of methionine-enkephalin and substance P-like immunoreactivity in normal human brain and in Huntington’s disease. Brain Res. 199(1), 147-160 (1980).

    5. Sakurada, T., Sakurada, S., Watanabe, S., et al. Comparison of the antinociceptive effects of intracerebroventricular injection of kyotorphin, cyclo (N-methyl-Tyr-Arg) and Met-enkephalin in mice. Neuropharmacology 23(1), 7-12 (1984).

    6. Jiang, Y.-L., He, X.-F., Shen, Y.-F., et al. Analgesic roles of peripheral intrinsic met-enkephalin and dynorphin A in long-lasting inflammatory pain induced by complete Freund’s adjuvant in rats. Exp. Ther. Med. 9(6), 2344-2348 (2015).