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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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D M Manchenko et al.
Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova, 96(10), 1014-1023 (2011-01-29)
Heptapeptide Semax (MEHFPGP) is the fragment of ACTH(4-10) analogue with prolonged neurotropic activity. The aim of the present work was to study the Semax effects on learning capability and pain sensitivity in white rats following intraperitoneal and intranasal administration in
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
A A Bakhmet et al.
Bulletin of experimental biology and medicine, 153(5), 661-663 (2012-11-01)
We studied the effect of antistress peptide Semax, an ACTH4-10 analogue, on the cellular composition of spleen lymphoid structures in Wistar rats with different stress tolerance in the course of post-stress recovery (days 1, 3, 14, and 30). Preliminary administration
Semax prevents functional impairments of avoidance response in rats.
A N Inozemtsev et al.
Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections, 448, 1-3 (2013-03-13)
K V Shevchenko et al.
Bioorganicheskaia khimiia, 37(4), 475-482 (2011-11-22)
Proteolysis of semax (Met-Glu-His-Phe-Pro-Gly-Pro, Sem) and its analogues ([Ala1]Sem, [Gly1]Sem, [Thr1]Sem, [Trp1]Sem) that are differ from semax in substitution of N-terminal Met residue were studied. It is shown that such replacement changes the rate of peptides degradation by N-aminopeptidases (EC
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