Thyrotropin-releasing hormone
Athanor · official
C16H22N6O4 · 362.38 g/mol
IUPAC name: (2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
Also called TRH, protirelin, thyroliberin, pyroGlu-His-Pro-NH2
WarningHarmful if inhaledNames and identifiers
- IUPAC name
- (2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
- Synonyms
- TRH, protirelin, thyroliberin
+ 39 more
pyroGlu-His-Pro-NH2, Thyroliberin, Lopremone, Synthetic TRH, Rifathyroin, Thypinone, Thyrotropin-releasing factor, TSH-releasing factor, Protireline, Thyrotropic-releasing factor, 5-Oxo-L-prolyl-L-histidyl-L-prolinamide, ABBOTT-38579, Protirelinum, THYREL TRH, Synthetic tsh-releasing factor, Relefact TRH, Abbott 38579, Protirelin, synthetic, Protirelina, DTXSID0023533, 5-oxo-pro-his-pro-nh2, L-Pyroglutamyl-L-histidyl-L-prolineamide, Protireline [INN-French], Protirelinum [INN-Latin], FDA 1725, L-Prolinamide, 5-oxo-L-prolyl-L-histidyl-, Protirelina [INN-Spanish], CCRIS 2593, (2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide, Ro 8-6270/9, Relefact TRH (TN), Protirelin [USAN:INN:BAN:JAN], PROTIRELIN [INN], PROTIRELIN [JAN], EINECS 246-143-4, PROTIRELIN [USAN], PROTIRELIN [VANDF], 5Y5F15120W, NSC-760113
- Molecular formula
- C16H22N6O4
- Empirical formula
- C8H11N3O2
- Molecular weight
- 362.38 g/mol
- Exact mass
- 362.17025
- CAS number
- 24305-27-9
- PubChem CID
- 638678
- Canonical SMILES
- C1CC(N(C1)C(=O)C(CC2=CN=CN2)NC(=O)C3CCC(=O)N3)C(=O)N
- Isomeric SMILES
- C1C[C@H](N(C1)C(=O)[C@H](CC2=CN=CN2)NC(=O)[C@@H]3CCC(=O)N3)C(=O)N
- InChI
- InChI=1S/C16H22N6O4/c17-14(24)12-2-1-5-22(12)16(26)11(6-9-7-18-8-19-9)21-15(25)10-3-4-13(23)20-10/h7-8,10-12H,1-6H2,(H2,17,24)(H,18,19)(H,20,23)(H,21,25)/t10-,11-,12-/m0/s1
- InChIKey
- XNSAINXGIQZQOO-SRVKXCTJSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 26
- Rings
- 3
- Aromatic rings
- 1
- Fraction sp³ carbons (Fsp3)
- 0.56
- H-bond donors
- 4
- H-bond acceptors
- 5
- Rotatable bonds
- 6
- TPSA (Ų)
- 150.3 computed here · PubChem 150
- Formal charge
- 0
- XLogP3
- -2.5 PubChem
- Complexity
- 597 PubChem
- Stereocenters
- 3 definedCIP: C5: S · C10: S · C23: S
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C53.03%
- H6.12%
- N23.19%
- O17.66%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- -1.81 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -0.69 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.67 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 362.39
- log P ≤ 5 (Crippen): -1.81
- H-bond donors ≤ 5: 4
- H-bond acceptors ≤ 10: 5
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
Warning
Most widely reported: 18 company reports to ECHA. Source [1].
- Harmful or irritant
- H332Harmful if inhaled (94.4% of reports)
Precautionary statements: P261, P271, P304+P340, P317
Safety data sheets on the supplier’s page: InvivoChem, AppChem, LGC Standards.
Always read the supplier’s safety data sheet before working with it.
Spectra
- NMRNMRShiftDB
- GC-MSNIST Mass Spectrometry Data Center
- MS-MSHuman Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive)
- LC-MSMassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · POSITIVE)
- Other MSMassBank of North America (MoNA) (qTof · negative) · MassBank of North America (MoNA) (qTof · positive)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [2]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
- [3]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- [4]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [5]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [6]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.