TRH free acid

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

MedKoo CAT#: 526905

CAS#: 24769-58-2

Description: 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

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TRH free acid
CAS# 24769-58-2
Instruction

Theoretical Analysis

MedKoo Cat#: 526905
Name: TRH free acid
CAS#: 24769-58-2
Chemical Formula: C16H21N5O5
Exact Mass: 363.15
Molecular Weight: 363.374
Elemental Analysis: C, 52.89; H, 5.83; N, 19.27; O, 22.01

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.