Compound monograph
Ipamorelin
Ipamorelin is a synthetic pentapeptide with a C-terminal amide, characterized in its original report as a growth hormone secretagogue acting through a GHRP-like receptor rather than the GHRH receptor.
01
Identity & nomenclature
Ipamorelin is a synthetic pentapeptide with a C-terminal amide, characterized in its original report as a growth hormone secretagogue acting through a GHRP-like receptor rather than the GHRH receptor.
Identified within a series of compounds lacking the central Ala-Trp dipeptide of growth hormone-releasing peptide-1. PubChem lists NNC 26-0161 as a development identifier.
Declared aliases and development codes: NNC 26-0161.
02
Molecular properties
| Molecular formula | C38H49N9O5 |
|---|---|
| Molecular mass | 711.9 Da |
| CAS Registry Number | 170851-70-4 |
| PubChem CID | 9831659 |
| UNII | Y9M3S784Z6 |
| Three-letter sequence | Aib–His–D-2-Nal–D-Phe–Lys |
Pentapeptide Aib-His-D-2-Nal-D-Phe-Lys-NH2. Contains alpha-aminoisobutyric acid, D-2-naphthylalanine, and D-phenylalanine, so a standard one-letter representation does not apply. The sequence is stated identically in the PubChem synonym record and in the original characterization paper.
03
Structural characteristics
Pharmacological profiling using GHRP and GHRH antagonists reported that ipamorelin acts via a GHRP-like receptor. The original report describes it as the first GHRP-receptor agonist whose selectivity for growth hormone release resembled that of GHRH, noting that plasma ACTH and cortisol were not raised significantly relative to GHRH stimulation even at doses more than 200-fold above the ED50 for growth hormone release, in contrast to GHRP-6 and GHRP-2. Structure-activity work on related analogs examined lysine mimetics combined with naphthyl- or biphenylalanine substitutions in the core.
- Alpha-aminoisobutyric acid (Aib) at position 1
- D-2-naphthylalanine at position 3
- D-phenylalanine at position 4
Terminal features: C-terminal amide.
04
Molecular targets & mechanisms
05
Analytical considerations
Three of the five residues are non-proteinogenic, and the C-terminus is amidated. Identity methods must resolve the D-configuration residues and the amide, which a sequence-only assay assuming L-amino acids will not distinguish.
06
Verified bibliography
- Ipamorelin, the first selective growth hormone secretagogue.current
Raun K, Hansen BS, Johansen NL, Thøgersen H, Madsen K, Ankersen M, Andersen PH
European journal of endocrinology · 1998-11 · Journal Article
- Highly potent growth hormone secretagogues: hybrids of NN703 and ipamorelin.current
Hansen TK, Ankersen M, Raun K, Hansen BS
Bioorganic & medicinal chemistry letters · 2001-07-23 · Journal Article
- current
- Growth hormone secretagogue receptor family members and ligands.current
Smith RG, Leonard R, Bailey AR, Palyha O, Feighner S, Tan C, Mckee KK, Pong SS, Griffin P, Howard A
Endocrine · 2001-02 · Review
- Structure of an antagonist-bound ghrelin receptor reveals possible ghrelin recognition mode.current
Shiimura Y, Horita S, Hamamoto A, Asada H, Hirata K, Tanaka M, Mori K, Uemura T, Kobayashi T, Iwata S, Kojima M
Nature communications · 2020-08-19 · Journal Article
- Determination of growth hormone releasing peptides (GHRP) and their major metabolites in human urine for doping controls by means of liquid chromatography mass spectrometry.current
Thomas A, Höppner S, Geyer H, Schänzer W, Petrou M, Kwiatkowska D, Pokrywka A, Thevis M
Analytical and bioanalytical chemistry · 2011-02-06 · Journal Article
10
Methodology & citation verification
Reference identity is checked against official PubMed metadata. Local deterministic receipts bind each normalized title and canonical metadata record to its verification date. Scientific values remain absent when an authoritative source has not been verified.
Read the full methodology →