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S8826

Sigma-Aldrich

Semax

≥98% (HPLC)

Synonym(s):

ACTH (4-7), Pro-Gly-Pro trifluoroacetate salt, L-Methionyl-L-a-glutamyl-L-histidyl-L-phenylalanyl-L-prolylglycyl-L-proline trifluoroacetate salt, Met-Glu-His-Phe-Pro-Gly-Pro

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About This Item

Empirical Formula (Hill Notation):
C37H51N9O10S · xC2HF3O2
CAS Number:
80714-61-0
Molecular Weight:
813.92 (free base basis)
MDL number:
MFCD04113563
UNSPSC Code:
51111800
PubChem Substance ID:
329824612
NACRES:
NA.32

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

H2O: >2 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

OC(=O)C(F)(F)F.CSCC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](Cc2ccccc2)C(=O)N3CCC[C@H]3C(=O)NCC(=O)N4CCC[C@H]4C(O)=O

InChI

1S/C37H51N9O10S.C2HF3O2/c1-57-16-13-24(38)32(50)42-25(11-12-31(48)49)33(51)43-26(18-23-19-39-21-41-23)34(52)44-27(17-22-7-3-2-4-8-22)36(54)46-15-5-9-28(46)35(53)40-20-30(47)45-14-6-10-29(45)37(55)56;3-2(4,5)1(6)7/h2-4,7-8,19,21,24-29H,5-6,9-18,20,38H2,1H3,(H,39,41)(H,40,53)(H,42,50)(H,43,51)(H,44,52)(H,48,49)(H,55,56);(H,6,7)/t24-,25-,26-,27-,28-,29-;/m0./s1

InChI key

UAXRUQRHZBYPHF-IGCYJKAMSA-N

General description

Semax regulates the expression and the activation of the hippocampal (brain-derived neurotrophic factor) BDNF/(tropomyosin receptor kinase B) trkB system. It enhances selective attention at the time of information reception, increases memory consolidation and stimulates learning abilities. Semax is an active element of SEMAX drugs, which is used for the treatment of brain hypoxia and ischemia. It stimulates the activity of choline acetyltransferase. Semax exhibits properties of the melanocortin (MC) receptor antagonist.

Biochem/physiol Actions

Semax (Met-Glu-His-Phe-Pro-Gly-Pro) is an analog of the adrenocorticotropin fragment (4-10). It activates the transcription of neurotrophins and has neuroprotective and nootropic activity.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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G A Romanova et al.
Patologicheskaia fiziologiia i eksperimental'naia terapiia, (3)(3), 62-67 (2012-10-18)
It was stated, that with bilateral photochemically induced thrombosis of the prefrontal cortex peptide semax and the AB-Glu by intranasal injection provoke pronounced neuroprotective and antiamnestic action. Intranasal injection semax (250 mkg/kg/daily during six postoperative days) and AB-Glu (250 mkg/kg
V V Stavchanskiĭ et al.
Molekuliarnaia biologiia, 45(6), 1026-1035 (2012-02-03)
Neurotrophins regulate key function of nervous tissue cells. Analysis of neurotrophins mRNA expression is an appropriate tool to assess therapeutic efficiency of the anti-stroke drugs. We have analyzed the effect of synthetic peptide semax and its C-terminal Pro-Gly-Pro tripeptide upon
Ex vivo screening of prospective peptide drugs: new approaches.
L A Andreeva et al.
Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections, 434, 300-303 (2010-10-22)
Vasily V Stavchansky et al.
Journal of molecular neuroscience : MN, 45(2), 177-185 (2010-07-10)
The neuropeptide preparation Semax (Met-Glu-His-Phe-Pro-Gly-Pro) has been employed successfully in clinical practice for treating patients with severe brain blood circulation disorders. In spite of numerous studies, many aspects of the therapeutic effects of this preparation remain unknown. In this context
Semax increases erythrocyte deformability in the shearing blood stream in intact rats and rats with cerebral ischemia.
O E Fadyukova et al.
Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections, 439, 208-211 (2011-09-29)
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