Adrenorphin

- Overview
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    Background
    
    Adrenorphin (metorphamide) is a potent inhibitor of nicotine-induced adrenaline and noradrenaline release with IC50 value of 10 μM [1].
    Adrenorphin (metorphamide) is an endogenous, C-terminally amidated, opioid octapeptide (Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH2) that is produced from proteolytic cleavage of proenkephalin A and is widely distributed throughout the mammalian brain [2].
    Adrenorphin (metorphamide) is selective nicotine-induced adrenaline and noradrenaline release inhibitor and has higher than 100-fold more potent than the reported nicotine-induced adrenaline and noradrenaline release inhibitor Met5-enkephalin. When tested with bovine adrenal chromaffin cells, Adrenorphin (metorphamide) showed inhibition on 5 μM nicotine-induced ATP release by almost 50% at 5μM and the inhibition was not in a dose-dependent manner [1]. In bioassays and binding assays, Metorphamide exhibited high μ-binding activity, as well as κ-binding activity with nearly half percent toμ-binding activity, while showed no activity on δ-binding [2].
    
    [1]. Marley, P.D., K.I. Mitchelhill, and B.G. Livett, Metorphamide, a novel endogenous adrenal opioid peptide, inhibits nicotine-induced secretion from bovine adrenal chromaffin cells. Brain Res, 1986. 363(1): p. 10-7.
    [2]. Weber, E., et al., Metorphamide: isolation, structure, and biologic activity of an amidated opioid octapeptide from bovine brain. Proc Natl Acad Sci U S A, 1983. 80(23): p. 7362-6.
- Properties
  - Categories
    
    Endogenous μ/κ opioid agonist, potent and selective
    
    Alternative Name
    
    H2N-Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-amide; Adrenorphin
    
    CAS Number
    
    88377-68-8
    
    Molecular Formula
    
    C44H69N15O9S
    
    Molecular Weight
    
    984.18
    
    Appearance
    
    A solid
    
    Purity
    
    97.00%
    
    Solubility
    
    insoluble in EtOH; ≥48.7 mg/mL in H2O; ≥98.4 mg/mL in DMSO
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    CC(C)C(C(=O)N)NC(=O)C(CCCN=C(N)N)NC(=O)C(CCCN=C(N)N)NC(=O)C(CCSC)NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)N
    
    * For Research Use Only