Isobutylamine

Isobutylamine
Names
	Preferred IUPAC name 2-Methylpropan-1-amine
	Other names (2-Methylpropyl)amine
Identifiers
CAS Number	78-81-9 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	385626
ChEBI	CHEBI:15997 ;
ChemSpider	6310 ;
ECHA InfoCard	100.001.042
EC Number	201-145-4;
Gmelin Reference	81862
KEGG	C02787 ;
MeSH	isobutylamine
PubChem CID	6558;
RTECS number	NP9900000;
UNII	1H60H4LOHZ ;
UN number	1214
CompTox Dashboard (EPA)	DTXSID9025459 ;
	InChI InChI=1S/C4H11N/c1-4(2)3-5/h4H,3,5H2,1-2H3 Key: KDSNLYIMUZNERS-UHFFFAOYSA-N ;
	SMILES CC(C)CN;
Properties
Chemical formula	C4H11N
Molar mass	73.139 g·mol−1
Appearance	Colorless liquid
Odor	Fishy, ammoniacal
Density	736 mg mL−1
Melting point	−86.6 °C; −124.0 °F; 186.5 K
Boiling point	67 to 69 °C; 152 to 156 °F; 340 to 342 K
Solubility in water	Miscible
Magnetic susceptibility (χ)	-59.8·10−6 cm3/mol
Refractive index (nD)	1.397
Viscosity	500 μPa s (at 20 °C)
Thermochemistry
Heat capacity (C)	194 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	−133.0–−132.0 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−3.0139–−3.0131 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H301, H314
Precautionary statements	P210, P280, P301+P310, P305+P351+P338, P310
Flash point	−9 °C (16 °F; 264 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	224 mg kg−1 (oral, rat)
Related compounds
Related alkanamines	Ethylamine; Ethylenediamine; Propylamine; Isopropylamine; 1,2-Diaminopropane; 1,3-Diaminopropane; tert-Butylamine; n-Butylamine; sec-Butylamine; Putrescine;
Related compounds	2-Methyl-2-nitrosopropane; N-Methylisobutylamine;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Isobutylamine is an organic chemical compound (specifically, an amine) with the formula (CH₃)₂CHCH₂NH₂, and occurs as a colorless liquid.^[1]^[2] Isobutylamine is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and tert-butylamine. It is the decarboxylated form of the amino acid valine, and the product of the metabolism thereof by the enzyme valine decarboxylase.

Isobutylamine is an odorant binding to TAAR3 in mice and can trigger sexual behaviour in male mice dependent on the cluster of TAAR2 through TAAR9.^[3]

References

^ Isobutylamine chemicalbook.com
^ Isobutylamine Chemblink.com
^ Harmeier A, Meyer CA, Staempfli A, Casagrande F, Petrinovic MM, Zhang YP, Künnecke B, Iglesias A, Höner OP, Hoener MC (2018). "How Female Mice Attract Males: A Urinary Volatile Amine Activates a Trace Amine-Associated Receptor That Induces Male Sexual Interest". Frontiers in Pharmacology. 9: 924. doi:10.3389/fphar.2018.00924. PMC 6104183. PMID 30158871.

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[1] Isobutylamine chemicalbook.com

[2] Isobutylamine Chemblink.com

[pmid30158871-3] Harmeier A, Meyer CA, Staempfli A, Casagrande F, Petrinovic MM, Zhang YP, Künnecke B, Iglesias A, Höner OP, Hoener MC (2018). "How Female Mice Attract Males: A Urinary Volatile Amine Activates a Trace Amine-Associated Receptor That Induces Male Sexual Interest". Frontiers in Pharmacology. 9: 924. doi:10.3389/fphar.2018.00924. PMC 6104183. PMID 30158871.

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