Isobutylamine

Summary

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
  • 78-81-9 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B00498
385626
ChEBI
  • CHEBI:15997 checkY
ChemSpider
  • 6310 checkY
ECHA InfoCard 100.001.042 Edit this at Wikidata
EC Number
  • 201-145-4
81862
KEGG
  • C02787 checkY
MeSH isobutylamine
  • 6558
RTECS number
  • NP9900000
UNII
  • 1H60H4LOHZ checkY
UN number 1214
  • DTXSID9025459 Edit this at Wikidata
  • 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).
☒N verify (what is checkY☒N ?)
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 edit

  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.