Isopentylamine

Isopentylamine
Names
	IUPAC name 3-methylbutan-1-amine
	Other names Isoamylamine; Isovaleramine; Leucamine; 3-Methylbutylamine;
Identifiers
CAS Number	107-85-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:43689;
ChEMBL	ChEMBL42003;
ChemSpider	7606;
ECHA InfoCard	100.003.206
EC Number	203-526-0;
IUPHAR/BPS	5506;
KEGG	C02640;
PubChem CID	7894;
UNII	LPO0L33SHY;
CompTox Dashboard (EPA)	DTXSID7059355 ;
	InChI InChI=1S/C5H13N/c1-5(2)3-4-6/h5H,3-4,6H2,1-2H3 Key: BMFVGAAISNGQNM-UHFFFAOYSA-N;
	SMILES CC(C)CCN;
Properties
Chemical formula	C5H13N
Molar mass	87.166 g·mol−1
Appearance	colorless
Density	0.747-0.753 g/cm3
Melting point	−60 °C (−76 °F; 213 K)
Boiling point	95–97 °C (203–207 °F; 368–370 K)
Solubility in water	soluble
Solubility	soluble in ethanol, propylene glycol, glycerin, oils
Refractive index (nD)	1.405-1.411
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H314, H315, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Isopentylamine, also known as isoamylamine, isovaleramine, or leucamine, is a naturally occurring aliphatic amine and alkylamine compound.^[2]^[3] It has been reported to produce sympathomimetic effects in preclinical research similarly to other alkylamines.^[2] The compound is a substrate for and is metabolized by the enzyme monoamine oxidase (MAO) similarly to phenethylamine.^[2] It is produced by certain bacteria and plants, for instance via decarboxylation of the amino acid leucine.^[2] Isopentylamine functions as an insecticide in plants.^[4] Gut bacteria-derived isopentylamine is enriched in older mice and humans and has been found to promote age-related cognitive dysfunction via microglial cell death in mice.^[5]

References

1 2 "Isoamylamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-10-08.
1 2 3 4 Peers EM, Lyles GA, Callingham BA (April 1980). "The deamination of isoamylamine by monamine oxidase in mitochondrial preparations from rat liver and heart: a comparison with phenylethylamine". Biochem Pharmacol. 29 (8): 1097–1102. doi:10.1016/0006-2952(80)90402-5. PMID 7387726.
↑ Api AM, Belsito D, Biserta S, Botelho D, Bruze M, Burton GA, Buschmann J, Cancellieri MA, Dagli ML, Date M, Dekant W, Deodhar C, Fryer AD, Gadhia S, Jones L, Joshi K, Lapczynski A, Lavelle M, Liebler DC, Na M, O'Brien D, Patel A, Penning TM, Ritacco G, Rodriguez-Ropero F, Romine J, Sadekar N, Salvito D, Schultz TW, Siddiqi F, Sipes IG, Sullivan G, Thakkar Y, Tokura Y, Tsang S (April 2020). "RIFM fragrance ingredient safety assessment, isopentylamine, CAS Registry Number 107-85-7". Food Chem Toxicol. 138 Suppl 1 111197. doi:10.1016/j.fct.2020.111197. PMID 32081730.
↑ Aboshi T, Iitsuka C, Galis I, Teraishi M, Kamo M, Nishimura A, Ishihara A, Mori N, Murayama T (January 2021). "Isopentylamine is a novel defence compound induced by insect feeding in rice". Plant Cell Environ. 44 (1): 247–256. Bibcode:2021PCEnv..44..247A. doi:10.1111/pce.13902. PMID 33034373.
↑ Teng Y, Mu J, Xu F, Zhang X, Sriwastva MK, Liu QM, Li X, Lei C, Sundaram K, Hu X, Zhang L, Park JW, Hwang JY, Rouchka EC, Zhang X, Yan J, Merchant ML, Zhang HG (July 2022). "Gut bacterial isoamylamine promotes age-related cognitive dysfunction by promoting microglial cell death". Cell Host Microbe. 30 (7): 944–960.e8. doi:10.1016/j.chom.2022.05.005. PMC 9283381. PMID 35654045.

[PubChem-1] 1 2 "Isoamylamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-10-08.

[PeersLylesCallingham1980-2] 1 2 3 4 Peers EM, Lyles GA, Callingham BA (April 1980). "The deamination of isoamylamine by monamine oxidase in mitochondrial preparations from rat liver and heart: a comparison with phenylethylamine". Biochem Pharmacol. 29 (8): 1097–1102. doi:10.1016/0006-2952(80)90402-5. PMID 7387726.

[ApiBelsitoBiserta2020-3] Api AM, Belsito D, Biserta S, Botelho D, Bruze M, Burton GA, Buschmann J, Cancellieri MA, Dagli ML, Date M, Dekant W, Deodhar C, Fryer AD, Gadhia S, Jones L, Joshi K, Lapczynski A, Lavelle M, Liebler DC, Na M, O'Brien D, Patel A, Penning TM, Ritacco G, Rodriguez-Ropero F, Romine J, Sadekar N, Salvito D, Schultz TW, Siddiqi F, Sipes IG, Sullivan G, Thakkar Y, Tokura Y, Tsang S (April 2020). "RIFM fragrance ingredient safety assessment, isopentylamine, CAS Registry Number 107-85-7". Food Chem Toxicol. 138 Suppl 1 111197. doi:10.1016/j.fct.2020.111197. PMID 32081730.

[AboshiIitsukaGalis2021-4] Aboshi T, Iitsuka C, Galis I, Teraishi M, Kamo M, Nishimura A, Ishihara A, Mori N, Murayama T (January 2021). "Isopentylamine is a novel defence compound induced by insect feeding in rice". Plant Cell Environ. 44 (1): 247–256. Bibcode:2021PCEnv..44..247A. doi:10.1111/pce.13902. PMID 33034373.

[TengMuXu2022-5] Teng Y, Mu J, Xu F, Zhang X, Sriwastva MK, Liu QM, Li X, Lei C, Sundaram K, Hu X, Zhang L, Park JW, Hwang JY, Rouchka EC, Zhang X, Yan J, Merchant ML, Zhang HG (July 2022). "Gut bacterial isoamylamine promotes age-related cognitive dysfunction by promoting microglial cell death". Cell Host Microbe. 30 (7): 944–960.e8. doi:10.1016/j.chom.2022.05.005. PMC 9283381. PMID 35654045.

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See also

References