Isobutylamine

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
Skeletal formula of isobutylamine
Names
Preferred IUPAC name
2-Methylpropan-1-amine
Other names
(2-Methylpropyl)amine
Identifiers
3D model (JSmol)
3DMet
385626
ChEBI
ChemSpider
ECHA InfoCard 100.001.042
EC Number
  • 201-145-4
81862
KEGG
MeSH isobutylamine
RTECS number
  • NP9900000
UNII
UN number 1214
  • InChI=1S/C4H11N/c1-4(2)3-5/h4H,3,5H2,1-2H3 checkY
    Key: KDSNLYIMUZNERS-UHFFFAOYSA-N checkY
  • CC(C)CN
Properties
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
Miscible
-59.8·10−6 cm3/mol
1.397
Viscosity 500 μPa s (at 20 °C)
Thermochemistry
194 J K−1 mol−1
−133.0–−132.0 kJ mol−1
−3.0139–−3.0131 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS06: Toxic
Danger
H225, H301, H314
P210, P280, P301+P310, P305+P351+P338, P310
Flash point −9 °C (16 °F; 264 K)
Lethal dose or concentration (LD, LC):
224 mg kg−1 (oral, rat)
Related compounds
Related alkanamines
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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
  1. Isobutylamine chemicalbook.com
  2. Isobutylamine Chemblink.com
  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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