A cyclic neuropeptide and metabolite of TRH
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Cyclo(L-His-L-Pro)

Item No. 31172

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,8aS)-hexahydro-3-(1H-imidazol-4-ylmethyl)-pyrrolo[1,2-a]pyrazine-1,4-dione
CAS Number
53109-32-3
Synonyms
  • Cyclo(His-Pro)
  • Cyclo(histidyl-proline)
  • Histidylproline diketopiperazine
  • Histidylproline dioxopiperazine
Molecular Formula
C11H14N4O2
Formula Weight
234.3
Purity
≥95%
Formulation (Request formulation change)
A neat oil
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 1 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
O=C(N1[C@@]2([H])CCC1)[C@H](CC3=CN=CN3)NC2=O
InChi Code
InChI=1S/C11H14N4O2/c16-10-9-2-1-3-15(9)11(17)8(14-10)4-7-5-12-6-13-7/h5-6,8-9H,1-4H2,(H,12,13)(H,14,16)/t8-,9-/m0/s1
InChi Key
NAKUGCPAQTUSBE-IUCAKERBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    10 mg

    $90

    Add

    25 mg

    $207

    Add

    50 mg

    $328

    Add

    100 mg

    $609

    Add
    Product Description

    Cyclo(L-His-L-Pro) is an endogenous cyclic neuropeptide and a metabolite of thyrotropin-releasing hormone (TRH).1 It is formed in the hypothalamus via the hydrolytic removal of pyroglutamic acid from TRH followed by non-enzymatic cyclization but is also synthesized de novo.2 It is ubiquitously expressed in the CNS, but is also found in the gastrointestinal tract and blood. Cyclo(L-His-L-Pro) (50 µM) reduces LPS-induced production of reactive oxygen species (ROS) and nitric oxide (NO), as well translocation of NF-κB in BV-2 microglia. Levels of cyclo(L-His-L-Pro) are increased in rat brain after six weeks of continuous ethanol consumption and cyclo(L-His-L-Pro) reduces ethanol-induced sleep time in rats when administered at a dose of 1 µmol/kg.1,3 Cyclo(L-His-L-Pro) induces analgesia in the hot-plate test and reduces acetic acid-induced writhing in mice, effects that can be partially reversed by the opioid antagonist naloxone.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Prasad, C. Neurobiology of cyclo(His-Pro). Ann. N. Y. Acad. Sci. 553(1), 232-251 (1989).

    2. Grottelli, S., Ferrari, I., Pietrini, G., et al. The role of cyclo(His-Pro) in neurodegeneration. Int. J. Mol. Sci. 17(8), 1332 (2016).

    3. Prasad, C., Matsui, T., and Peterkofsky, A. Antagonism of ethanol narcosis by histidyl-proline diketopiperazine. Nature 268(5616), 142-144 (1977).