WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H597822
CAS#: 62305-86-6
Description: Orotirelin is an analogue of Thyrotropin-releasing hormone with possible therapeutic application in sleep disorders. It increases dopamine release from rat brain.
Hodoodo Cat#: H597822
Name: Orotirelin
CAS#: 62305-86-6
Chemical Formula: C16H19N7O5
Exact Mass: 389.14
Molecular Weight: 389.370
Elemental Analysis: C, 49.36; H, 4.92; N, 25.18; O, 20.54
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Synonym: Orotirelin; CG 3509; Orotireline;
IUPAC/Chemical Name: N-((S)-1-((S)-2-carbamoylpyrrolidin-1-yl)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamide
InChi Key: XZOCIZHAHWDUPU-QWRGUYRKSA-N
InChi Code: InChI=1S/C16H19N7O5/c17-13(25)11-2-1-3-23(11)15(27)10(4-8-6-18-7-19-8)20-14(26)9-5-12(24)22-16(28)21-9/h5-7,10-11H,1-4H2,(H2,17,25)(H,18,19)(H,20,26)(H2,21,22,24,28)/t10-,11-/m0/s1
SMILES Code: O=C(N)[C@H]1N(C([C@H](CC2=CNC=N2)NC(C(NC3=O)=CC(N3)=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: >3 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: 2934.99.03.00
More Info:
| Biological target: | |
| In vitro activity: | |
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The following data is based on the product molecular weight 389.37 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.
| 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: |
1: Faden AI, Jacobs TP. Effect of TRH analogs on neurologic recovery after experimental spinal trauma. Neurology. 1985 Sep;35(9):1331-4. PubMed PMID: 3927187.
2: Bennett GW, Edwards RM, Lighton C, Marsden CA. Thyrotrophin releasing hormone--5-hydroxytryptamine interactions in the brain studied using chronic immunization and chemical lesioning techniques. J Recept Res. 1987;7(1-4):555-79. PubMed PMID: 3040985.
3: Shrewsbury-Gee J, Lye RH, Latham A, Slater P. The effects of TRH analogues on cerebral ischaemia produced by middle cerebral artery occlusion in the rat. Exp Brain Res. 1988;70(2):342-50. PubMed PMID: 3133237.
4: Amir S, Pollock R, Lagiorgia M. Intra-hypothalamic injection of thyrotropin-releasing hormone suppresses brown fat thermogenesis in the anaesthetized rat. Brain Res. 1989 Jan 30;478(2):361-4. PubMed PMID: 2493964.
5: Pranzatelli MR, Dailey A, Markush S. The regulation of TRH and serotonin receptors: chronic TRH and analog administration in the rat. J Recept Res. 1988;8(5):667-81. PubMed PMID: 2839679.
6: Griffiths EC, Rothwell NJ, Stock MJ. Thermogenic effects of thyrotrophin-releasing hormone and its analogues in the rat. Experientia. 1988 Jan 15;44(1):40-2. PubMed PMID: 3127235.
7: Sharp T, Tulloch IF, Bennett GW, Marsden CA, Metcalf G, Dettmar PW. Analeptic effects of centrally injected TRH and analogues of TRH in the pentobarbitone-anaesthetized rat. Neuropharmacology. 1984 Mar;23(3):339-48. PubMed PMID: 6145113.
8: Heal DJ, Stoodley N, Elliott JM, Marsden CA, Bennett GW, Youdim MB. Behavioural and biochemical evidence for the release of noradrenaline in mouse brain by TRH and some of its biologically stable analogues. Neuropharmacology. 1987 Apr;26(4):313-22. PubMed PMID: 2884590.
9: Marsden CA, Bennett GW, Fone KC, Johnson JV. Functional interactions between TRH and 5-hydroxytryptamine (5-HT) and proctolin in rat brain and spinal cord. Ann N Y Acad Sci. 1989;553:121-34. PubMed PMID: 2566294.
10: Fone KC, Bennett GW, Marsden CA. Involvement of catecholaminergic neurones and alpha-adrenoceptors in the wet-dog shake and forepaw licking behaviour produced by the intrathecal injection of an analogue of thyrotrophin-releasing hormone (CG 3509). Neuropharmacology. 1987 Aug;26(8):1147-55. PubMed PMID: 2889164.
11: Thielen T, Stober T, Schimrigk K. Therapeutic trial of intrathecal thyrotropin-releasing hormone (TRH) and a TRH-analogue in amyotrophic lateral sclerosis (ALS). Adv Exp Med Biol. 1987;209:305-8. PubMed PMID: 3107352.
12: Fone KC, Johnson JV, Marsden CA, Bennett GW. Comparative behavioural and biochemical effects of repeated intrathecal administration of thyrotrophin-releasing hormone (TRH) or two analogues of TRH in adult rats. Neuropharmacology. 1989 Aug;28(8):867-75. PubMed PMID: 2476681.
13: Lighton C, Bennett GW, Marsden CA. Chronic immunization of endogenous thyrotrophin-releasing hormone (TRH) in brain alters the behavioural response to pentobarbital and a TRH analogue. Brain Res. 1986 Jul 23;378(2):385-9. PubMed PMID: 3089541.
14: Fone KC, Johnson JV, Bennett GW, Marsden CA. Involvement of 5-HT2 receptors in the behaviours produced by intrathecal administration of selected 5-HT agonists and the TRH analogue (CG 3509) to rats. Br J Pharmacol. 1989 Mar;96(3):599-608. PubMed PMID: 2470455; PubMed Central PMCID: PMC1854385.
15: Sharp T, Bennett GW, Marsden CA. Thyrotrophin-releasing hormone analogues increase dopamine release from slices of rat brain. J Neurochem. 1982 Dec;39(6):1763-6. PubMed PMID: 6815305.
16: Sharp T, Bennett GW, Marsden CA, Tulloch IF. A comparison of the locomotor effects induced by centrally injected TRH and TRH analogues. Regul Pept. 1984 Nov;9(4):305-15. PubMed PMID: 6441196.
17: Amir S. Aging blocks the thermoregulatory action of thyrotropin-releasing hormone in anaesthetized rats. Brain Res. 1988 Feb 2;440(1):181-4. PubMed PMID: 3129125.
18: Sharp T, Brazell MP, Bennett GW, Marsden CA. The TRH analogue CG3509 increases in vivo catechol/ascorbate oxidation in the N. accumbens but not in the striatum of the rat. Neuropharmacology. 1984 Jun;23(6):617-23. PubMed PMID: 6431310.
19: Bristow LJ, Bennett GW. Effect of chronic intra-accumbens administration of the TRH analogue CG3509 on histamine-induced behaviour in the rat. Br J Pharmacol. 1989 Jul;97(3):745-52. PubMed PMID: 2503226; PubMed Central PMCID: PMC1854565.
20: Johnson JV, Fone KC, Havler ME, Tulloch IF, Bennett GW, Marsden CA. A comparison of the motor behaviours produced by the intrathecal administration of thyrotrophin-releasing hormone and thyrotrophin-releasing hormone analogues in the conscious rat. Neuroscience. 1989;29(2):463-70. PubMed PMID: 2498761.
