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MedKoo Cat#: 526905 | Name: TRH free acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

TRH free acid, also known as Deamido-TRH; Pglu-his-pro; Pyroglutamyl-histidyl-proline; TRH-deamido, is an analogs of thyrotropin-releasing hormone with activity to potentiate the spinal monosynaptic reflex in vitro.

Chemical Structure

TRH free acid
TRH free acid
CAS#24769-58-2

Theoretical Analysis

MedKoo Cat#: 526905

Name: TRH free acid

CAS#: 24769-58-2

Chemical Formula: C16H21N5O5

Exact Mass: 363.1543

Molecular Weight: 363.37

Elemental Analysis: C, 52.89; H, 5.83; N, 19.27; O, 22.01

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
TRH free acid; Deamido-TRH; Pglu-his-pro; Pyroglutamyl-histidyl-proline; TRH-deamido. Thyrotropin-releasing hormone, deamido-.
IUPAC/Chemical Name
((S)-5-oxopyrrolidine-2-carbonyl)-L-histidyl-L-proline
InChi Key
InChi Code
SMILES Code
O=C(O)[C@H]1N(C([C@H](CC2=CNC=N2)NC([C@H](CC3)NC3=O)=O)=O)CCC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 363.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kagabu Y, Mishiba T, Okino T, Yanagisawa T. Effects of thyrotropin-releasing hormone and its metabolites, Cyclo(His-Pro) and TRH-OH, on growth hormone and prolactin synthesis in primary cultured pituitary cells of the common carp, Cyprinus carpio. Gen Comp Endocrinol. 1998 Sep;111(3):395-403. PubMed PMID: 9707485. 2: Deshpande SB, Warnick JE. Analogs of thyrotropin-releasing hormone in potentiating the spinal monosynaptic reflex in vitro. Eur J Pharmacol. 1994 Dec 27;271(2-3):439-44. PubMed PMID: 7705444. 3: Salers P. Enhancement by streptozotocin-induced diabetes of pancreatic prolyl endopeptidase activity in neonatal rats. Regul Pept. 1994 Feb 24;50(2):101-11. PubMed PMID: 8190911. 4: Strbák V, Giraud P, Resetková E, Ouafik LH, Dutour A, Oliver C, Povazanová K, Randuskovà A. Thyroliberin (TRH) and TRH free acid (TRH-OH) present in milk do not originate from local synthesis in mammary gland. Endocr Regul. 1991 Jun;25(1-2):134-8. PubMed PMID: 1958827. 5: López-Barneo J, Castellano A, Toledo-Aral J. Thyrotropin-releasing-hormone (TRH) and its physiological metabolite TRH-OH inhibit Na+ channel activity in mammalian septal neurons. Proc Natl Acad Sci U S A. 1990 Oct;87(20):8150-4. PubMed PMID: 2172974; PubMed Central PMCID: PMC54910. 6: Møss J, Bundgaard H. Kinetics and pattern of degradation of thyrotropin-releasing hormone (TRH) in human plasma. Pharm Res. 1990 Jul;7(7):751-5. PubMed PMID: 2118634. 7: Merchenthaler I, Csernus V, Csontos C, Petrusz P, Mess B. New data on the immunocytochemical localization of thyrotropin-releasing hormone in the rat central nervous system. Am J Anat. 1988 Apr;181(4):359-76. PubMed PMID: 3133939. 8: Reny-Palasse V, Rips R. Antinociceptive activity of TRH metabolites in the mouse. Pain. 1987 Aug;30(2):259-69. PubMed PMID: 3118323. 9: Okuda C, Mizobe T, Miyazaki M. The involvement of central cholinergic mechanisms in cardiovascular responses to intracerebroventricular and intravenous administration of thyrotropin-releasing hormone. Life Sci. 1987 Mar 30;40(13):1293-9. PubMed PMID: 3104710. 10: Alexandrová M, Strbák V, Herman ZS, Stachura Z, Kruszyński M. Biological activity of TRH thionalogue and its diastereoisomers. Endocrinol Exp. 1987 Mar;21(1):43-9. PubMed PMID: 3106009. 11: Roussel JP, Tapia-Arancibia L, Astier H, Klingler W. In vitro and in vivo TSH releasing activity of two new analogues of TRH. Acta Endocrinol (Copenh). 1987 Feb;114(2):314-20. PubMed PMID: 3103364. 12: Koskinen LO. Effect of low intravenous doses of TRH, acid-TRH and cyclo(His-Pro) on cerebral and peripheral blood flows. Br J Pharmacol. 1986 Mar;87(3):509-19. PubMed PMID: 3099875; PubMed Central PMCID: PMC1916574. 13: Ouafik L, Dutour A, Giraud P, Boudouresque F, Castanas E, Oliver C. [Demonstration of a TRH precursor in the pancreas of the newborn rat]. Ann Endocrinol (Paris). 1986;47(1):43-4. French. PubMed PMID: 3094424. 14: Kruszyński M, Kupryszewski G, Ragnarsson U, Alexandrova M, Strbak V, Tonon MC, Vaudry H. TRH analogue with C-terminal thioamide group. Synthesis, receptor binding, TSH-releasing activity and alpha-MSH-releasing activity. Experientia. 1985 Dec 15;41(12):1576-7. PubMed PMID: 3000815. 15: Angyal R, Strbák V, Alexandrová M, Kruszyński M. TRH analogue with C-terminal thioamide group: rapid degradation by plasma and its biological effects. Endocrinol Exp. 1985 Dec;19(4):213-9. PubMed PMID: 3002750. 16: Dutour A, Ouafik L, Castanas E, Boudouresque F, Oliver C. TRH and TRH-OH in the pancreas of adult and newborn rats. Life Sci. 1985 Jul 15;37(2):177-83. PubMed PMID: 3925268. 17: Scanes CG, Harvey S, Bolaffi JL. TRH stimulation of in vivo GH release in the domestic fowl. Influence of TRH metabolites and effect of age on in vitro degradation of TRH. Neuroendocrinology. 1985 Jan;40(1):33-8. PubMed PMID: 3918278. 18: Safran M, Wu CF, Matys R, Alex S, Emerson CH. The pharmacokinetics of thyrotropin-releasing hormone (TRH) and deamido-TRH in the rat. Endocrinology. 1984 Sep;115(3):1031-7. PubMed PMID: 6430680. 19: Grimm-Jørgensen Y, Connolly SM, Visser TJ. Effect of thyrotropin-releasing hormone and its metabolites on the secretion of sulfated polysaccharides by foot integument of a pond snail. Gen Comp Endocrinol. 1984 Sep;55(3):410-7. PubMed PMID: 6147294. 20: Hedner J, Hedner T, Wessberg P, Lundberg D, Jonason J. Effects of TRH and TRH analogues on the central regulation of breathing in the rat. Acta Physiol Scand. 1983 Mar;117(3):427-37. PubMed PMID: 6410685.