An octapeptide agonist of μ-opioid receptors
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Adrenorphin (human, mouse, rat, bovine) (trifluoroacetate salt)

Item No. 35826

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-tyrosylglycylglycyl-L-phenylalanyl-L-methionyl-L-arginyl-L-arginyl-L-valinamide, trifluoroacetate salt
Synonyms
  • Met5-Enkephalin-Arg6-Arg7-Val8-NH2
  • Metorphamide
  • Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH2
Molecular Formula
C44H69N15O9 • XCF3COOH
Formula Weight
952.1
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
CC(C)[C@@H](C(N)=O)NC([C@H](CCCNC(N)=N)NC([C@H](CCCNC(N)=N)NC([C@H](CCSC)NC([C@@H](NC(CNC(CNC([C@@H](N)CC1=CC=C(C=C1)O)=O)=O)=O)CC2=CC=CC=C2)=O)=O)=O)=O.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C44H69N15O9S.C2HF3O2/c1-25(2)36(37(46)63)59-41(67)31(12-8-19-52-44(49)50)57-39(65)30(11-7-18-51-43(47)48)56-40(66)32(17-20-69-3)58-42(68)33(22-26-9-5-4-6-10-26)55-35(62)24-53-34(61)23-54-38(64)29(45)21-27-13-15-28(60)16-14-27;3-2(4,5)1(6)7/h4-6,9-10,13-16,25,29-33,36,60H,7-8,11-12,17-24,45H2,1-3H3,(H2,46,63)(H,53,61)(H,54,64)(H,55,62)(H,56,66)(H,57,65)(H,58,68)(H,59,67)(H4,47,48,51)(H4,49,50,52);(H,6,7)/t29-,30-,31-,32-,33-,36-;/m0./s1
InChi Key
QAXMQVLLILLPAV-MWIHCNFISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $29

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    5 mg

    $120

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    10 mg

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    25 mg

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    Product Description

    Adrenorphin is an octapeptide agonist of μ-opioid receptors that is involved in nociception.1,2 It is a C-terminally amidated cleavage product corresponding to amino acids 210-218 of human proenkephalin A. It was originally found in a human pheochromocytoma but has also been found in the rat adrenal medulla and the rat olfactory bulb, hypothalamus, and striatum, among other brain regions.1,3,4 Adrenorphin selectively binds to μ-opioid receptors over κ- and δ-opioid receptors (Kis = 0.12, 0.248, and 2.65 nM, respectively, in a radioligand binding assay).1 Intracerebroventricular administration of adrenorphin (6.1 nmol/animal) increases the latency to paw licking in the hot plate test in mice, indicating analgesic activity, an effect that can be reduced by the non-selective opioid receptor antagonist naloxone.2 It also induces respiratory depression in mice and rabbits (ED50s = 6 and 71.1 nmol/animal, respectively).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Weber, E., Esch, F.S., Bohlen, P., et al. Metorphamide: Isolation, structure, and biologic activity of an amidated opioid octapeptide from bovine brain. Proc. Natl. Acad. Sci. USA 80(23), 7362-7366 (1983).

    2. Xu, S.F., Lu, W.X., Zhou, K.R., et al. The analgesic and respiratory depressant actions of metorphamide in mice and rabbits. Neuropeptides 6(2), 121-131 (1985).

    3. Miyata, A., Mizuno, K., Honzawa, M., et al. Adrenorphin immunoreactivity in rat brain. Neuropeptides 5(4-6), 517-520 (1985).

    4. Zamir, N., Weber, E., Palkovits, M., et al. Distribution of immunoreactive metorphamide (adrenorphin) in discrete regions of the rat brain: Comparison with Met-enkephalin-Arg6-Gly7-Leu8. Brain Res. 361(1-2), 193-199 (1985).