Indolepropionamide

Indolepropionamide
Names
	Preferred IUPAC name 3-(1H-Indol-3-yl)propanamide
	Other names 3-Indolepropionamide; Indole-3-propanamide
Identifiers
CAS Number	5814-93-7;
3D model (JSmol)	Interactive image;
ChemSpider	312353;
PubChem CID	351791;
UNII	6RD94WRM73 ;
CompTox Dashboard (EPA)	DTXSID40326054 ;
	InChI InChI=1S/C11H12N2O/c12-11(14)6-5-8-7-13-10-4-2-1-3-9(8)10/h1-4,7,13H,5-6H2,(H2,12,14) Key: OTVHXWFANORBAK-UHFFFAOYSA-N;
	SMILES c1ccc2c(c1)c(c[nH]2)CCC(=O)N;
Properties
Chemical formula	C11H12N2O
Molar mass	188.230 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Indolepropionamide (IPAM) is a chemical compound with the molecular formula C₁₁H₁₂N₂O. In vivo (rats), IPAM markedly reduced the proton potential collapse induced by the mitochondrial toxins to nearly baseline levels in both young and old rats and demonstrated free-radical scavenging properties. IPAM was shown to increase complex I and complex IV activity in the mitochondrial electron transport chain, however complex II and complex III were left unchanged. Decreased activity of complexes I and IV results in an inhibition of electron transport that is associated with higher production of ROS. IPAM can also act as a recyclable electron and proton carrier, facilitating reversible endogenous radical and redox reactions, and thereby enabling the formation of a proton gradient that drives mitochondrial ATP synthesis. Thus, IPAM acts as a stabilizer of energy metabolism in mitochondria, thereby reducing the production of reactive oxygen species.^[1]

IPAM-treated rotifers (Philodina acuticornis) had a lifespan extended by approximately 300%, the number of offsprings increased by 3.4 times and body length increased by 1.47 times, in comparison with IPAM-untreated rotifers. Researchers noted, that such a lifespan extension in this particular rotifer species is the highest that was ever observed to date in any study. Indolepropionamide shows potential as an anti-aging molecule, a mitochondrial metabolism modifier and may have a therapeutic value in age-related neurodegenerative, and mitochondrial diseases.^[1]

In rodents, IPAM was detected as endogenously occurring and its levels can be slightly increased after administration of L-tryptophan (but not IPA or melatonin). IPAM has high bioavailability as it can efficiently cross the blood-brain barrier and remain at high concentrations in rat brains for several hours. In rats, IPAM was administered at a dosage of 0.5mg/kg.^[1]

References

^ ^a ^b ^c Poeggeler, Burkhard; Sambamurti, Kumar; Siedlak, Sandra L.; Perry, George; Smith, Mark A.; Pappolla, Miguel A. (2010). "A Novel Endogenous Indole Protects Rodent Mitochondria and Extends Rotifer Lifespan". PLOS ONE. 5 (4): e10206. Bibcode:2010PLoSO...510206P. doi:10.1371/journal.pone.0010206. PMC 2858081. PMID 20421998. Text was copied from this source, which is available under a Creative Commons Attribution 4.0 International License.

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[AutoIA-1-1] Poeggeler, Burkhard; Sambamurti, Kumar; Siedlak, Sandra L.; Perry, George; Smith, Mark A.; Pappolla, Miguel A. (2010). "A Novel Endogenous Indole Protects Rodent Mitochondria and Extends Rotifer Lifespan". PLOS ONE. 5 (4): e10206. Bibcode:2010PLoSO...510206P. doi:10.1371/journal.pone.0010206. PMC 2858081. PMID 20421998. Text was copied from this source, which is available under a Creative Commons Attribution 4.0 International License.

[1]

See also

References