| Stereochemistry | ABSOLUTE |
| Molecular Formula | C14H19N2O2.Cl |
| Molecular Weight | 282.766 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].C[N+](C)(C)[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
InChI
InChIKey=NZXZRRFENSICAK-ZOWNYOTGSA-N
InChI=1S/C14H18N2O2.ClH/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12;/h4-7,9,13,15H,8H2,1-3H3;1H/t13-;/m0./s1
Hypaphorine is the alkaloid isolated from the seeds of Brazilian medicinal plant Erythrina spp. This compound was investigated for sleep-promoting effects in mice, and the results showed that it significantly increased non-rapid eye movement (NREM) sleep time during the first hour after its administration. Hypaphorine prevented the differentiation of 3T3-L1 preadipocytes into adipocytes by down-regulating hormone-stimulated protein expression of peroxisome proliferator activated receptor γ (PPARγ) and CCAAT/enhancer binding protein (C/EBPα), and their downstream targets, sterol regulatory element binding protein 1 c (SREBP1c) and fatty acid synthase (FAS). Hypaphorine may exert anti-inflammatory actions through the regulation of TLR4 and PPAR-γ dependent on PI3K/Akt/mTOR signal pathways. It is considered as a therapeutic agent that can potentially relieve or ameliorate endothelial inflammation-associated diseases. Hypaphorine was also a key component of Vaccaria segetalis. Vaccaria hypaphorine might be considered as a potential therapeutic agent for treating osteoclast-based bone loss.
CNS Activity
Originator
Approval Year
PubMed
Sample Use Guides
Mice: 10 and 30 mg/kg (1 d before LPS injection and then every other 7 d.
Route of Administration:
Oral
SUBSTANCE RECORD
