Phe-Met-Arg-Phe amide trifluoroacetate

For research use only. Not for therapeutic Use.

  • CAT Number: I013094
  • CAS Number: 159237-99-7
  • Molecular Formula: C33H44F6N8O8S
  • Molecular Weight: 826.81
  • Purity: ≥95%
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Phe-Met-Arg-Phe amide trifluoroacetate is an activator of K+ current, with ED50 of 23 nM in the peptidergic caudodorsal neurons.
In the molluscan central nervous system, Phe-Met-Arg-Phe amide (FMRFa) acts on K+ channels in sensory, motor-, and neuroendocrine neurones. Phe-Met-Arg-Phe amide activates a novel K+ current that is characterized by a combined voltage- and receptor-dependent gating mechanism, with both factors being necessary for opening of the channels[1]. Phe-Met-Arg-Phe amide (1 μM) significantly inhibits glucose stimulated (300 mg/dL) insulin release (p<0.005) and somatostatin release (p<0.01) from the isolated perfused pancreas. Phe-Met-Arg-Phe amide (FMRF-NH2) (1 and 10 μM) is without effect on glucagon secretion, either in low glucose (50 mg/dL), high glucose (300 mg/dL), or during arginine stimulation (5 mM)[2].
Phe-Met-Arg-Phe amide (FMRFamide) stimulates growth hormone secretion in conscious OVX rats. The presence of Phe-Met-Arg-Phe amide-like immunoreactivity in neuronal elements in the hypothalamus suggested a role for this in the hypothalamic control of the anterior pituitary function. The injection of 200 ng (313.8 picomoles) of FMRFamide (in 2 uL) produces a significantly increased plasma GH 15 min after injection. The GH-increasing effect of 400-800 ng (627-1255 picomoles) of FMRFamide is already developed after 5 min and lasted up to 30 min[3].


Catalog Number I013094
CAS Number 159237-99-7
Synonyms

(2S)-N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-2-[[(2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-(diaminomethylideneamino)pentanamide;2,2,2-trifluoroacetic acid

Molecular Formula C33H44F6N8O8S
Purity ≥95%
InChI InChI=1S/C29H42N8O4S.2C2HF3O2/c1-42-16-14-23(35-26(39)21(30)17-19-9-4-2-5-10-19)28(41)36-22(13-8-15-34-29(32)33)27(40)37-24(25(31)38)18-20-11-6-3-7-12-20;2*3-2(4,5)1(6)7/h2-7,9-12,21-24H,8,13-18,30H2,1H3,(H2,31,38)(H,35,39)(H,36,41)(H,37,40)(H4,32,33,34);2*(H,6,7)/t21-,22-,23-,24-;;/m0../s1
InChIKey XVODPBULIXCTET-PAHQJZCISA-N
SMILES CSCCC(C(=O)NC(CCCN=C(N)N)C(=O)NC(CC1=CC=CC=C1)C(=O)N)NC(=O)C(CC2=CC=CC=C2)N.C(=O)(C(F)(F)F)O.C(=O)(C(F)(F)F)O
Reference

[1]. Kits KS, et al. Phe-Met-Arg-Phe-amide activates a novel voltage-dependent K+ current through a lipoxygenasepathway in molluscan neurones. J Gen Physiol. 1997 Nov;110(5):611-28.
 [Content Brief]

[2]. Sorenson RL, et al. Phe-met-arg-phe-amide (FMRF-NH2) inhibits insulin and somatostatin secretion and anti-FMRF-NH2 sera detects pancreatic polypeptide cells in the rat islet. Peptides. 1984 Jul-Aug;5(4):777-82.
 [Content Brief]

[3]. Ottlecz A, et al. Phe-Met-Arg-Phe-amide (FMRFamide) stimulated growth hormone secretion in conscious OVX rats. Neuropeptides. 1987 Feb-Mar;9(2):161-7.
 [Content Brief]

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