Isobutylamine

Last updated
Isobutylamine
Isobutylamine.svg
Isobutylamine-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-145-4
81862
KEGG
MeSH isobutylamine
PubChem CID
RTECS number
  • NP9900000
UNII
UN number 1214
  • InChI=1S/C4H11N/c1-4(2)3-5/h4H,3,5H2,1-2H3 Yes check.svgY
    Key: KDSNLYIMUZNERS-UHFFFAOYSA-N Yes check.svgY
  • CC(C)CN
Properties
C4H11N
Molar mass 73.139 g·mol−1
AppearanceColorless 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:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Related Research Articles

Valine (symbol Val or V) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO form under biological conditions), and a side chain isopropyl group, making it a non-polar aliphatic amino acid. Valine is essential in humans, meaning the body cannot synthesize it; it must be obtained from dietary sources which are foods that contain proteins, such as meats, dairy products, soy products, beans and legumes. It is encoded by all codons starting with GU (GUU, GUC, GUA, and GUG).

<span class="mw-page-title-main">Pheromone</span> Secreted or excreted chemical factor that triggers a social response in members of the same species

A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavior of the receiving individuals. There are alarm pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology. Pheromones are used by many organisms, from basic unicellular prokaryotes to complex multicellular eukaryotes. Their use among insects has been particularly well documented. In addition, some vertebrates, plants and ciliates communicate by using pheromones. The ecological functions and evolution of pheromones are a major topic of research in the field of chemical ecology.

Amination is the process by which an amine group is introduced into an organic molecule. This type of reaction is important because organonitrogen compounds are pervasive.

<span class="mw-page-title-main">Branched-chain amino acid</span> Amino acid with a branched carbon chain

A branched-chain amino acid (BCAA) is an amino acid having an aliphatic side-chain with a branch. Among the proteinogenic amino acids, there are three BCAAs: leucine, isoleucine, and valine. Non-proteinogenic BCAAs include 2-aminoisobutyric acid and alloisoleucine.

<span class="mw-page-title-main">Ammonia borane</span> Chemical compound

Ammonia borane, also called borazane, is the chemical compound with the formula H3NBH3. The colourless or white solid is the simplest molecular boron-nitrogen-hydride compound. It has attracted attention as a source of hydrogen fuel, but is otherwise primarily of academic interest.

Trace amine-associated receptors (TAARs), sometimes referred to as trace amine receptors, are a class of G protein-coupled receptors that were discovered in 2001. TAAR1, the first of six functional human TAARs, has gained considerable interest in academic and proprietary pharmaceutical research due to its role as the endogenous receptor for the trace amines phenethylamine, tyramine, and tryptamine – metabolic derivatives of the amino acids phenylalanine, tyrosine and tryptophan, respectively – ephedrine, as well as the synthetic psychostimulants, amphetamine, methamphetamine and methylenedioxymethamphetamine. In 2004, it was shown that mammalian TAAR1 is also a receptor for thyronamines, decarboxylated and deiodinated relatives of thyroid hormones. TAAR2–TAAR9 function as olfactory receptors for volatile amine odorants in vertebrates.

The carbylamine reaction is the synthesis of an isocyanide by the reaction of a primary amine, chloroform, and base. The conversion involves the intermediacy of dichlorocarbene.

<span class="mw-page-title-main">Phenyl-2-nitropropene</span> Chemical compound

1-Phenyl-2-nitropropene, or simply phenyl-2-nitropropene, or P2NP, as it is commonly referred to, is a chemical compound from the aromatic group of compounds, with the formula C9H9NO2. It is a light-yellow crystalline solid with a distinct smell. Phenyl-2-nitropropene is used in the pharmaceutical industry to manufacture the drug Adderall, an amphetamine mixture used to treat ADHD and narcolepsy. P2NP and other similar nitrostyrenes are also employed in the clandestine manufacture of drugs of the amphetamine class, and are listed as drug precursors in many countries.

<i>n</i>-Butylamine Chemical compound

n-Butylamine is an organic compound (specifically, an amine) with the formula CH3(CH2)3NH2. This colourless liquid is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine, and isobutylamine. It is a liquid having the fishy, ammonia-like odor common to amines. The liquid acquires a yellow color upon storage in air. It is soluble in all organic solvents. Its vapours are heavier than air and it produces toxic oxides of nitrogen during combustion.

<i>tert</i>-Butylamine Chemical compound

tert-Butylamine (also erbumine and other names) is an organic chemical compound with the formula (CH3)3CNH2. It is a colorless liquid with a typical amine-like odor. tert-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and isobutylamine.

<i>sec</i>-Butylamine Chemical compound

sec-Butylamine is an organic chemical compound (specifically, an amine) with the formula CH3CH2CH(NH2)CH3. It is a colorless liquid. sec-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, tert-butylamine, and isobutylamine. sec-Butylamine is chiral and therefore can exist in either of two enantiomeric forms.

The molecular formula C4H11N may refer to:

<span class="mw-page-title-main">TAAR2</span> Protein-coding gene in the species Homo sapiens

Trace amine-associated receptor 2 (TAAR2), formerly known as G protein-coupled receptor 58 (GPR58), is a protein that in humans is encoded by the TAAR2 gene. TAAR2 is coexpressed with Gα proteins; however, as of February 2017, its signal transduction mechanisms have not been determined.

<span class="mw-page-title-main">TAAR3</span> Human pseudogene

Putative trace amine-associated receptor 3 (TAAR3) is a human pseudogene with the gene symbol TAAR3P. In other species such as mice, TAAR3 is a functional protein-coding gene that encodes a trace amine-associated receptor protein.

<span class="mw-page-title-main">TAAR6</span> Protein and coding gene in humans

Trace amine associated receptor 6, also known as TAAR6, is a protein which in humans is encoded by the TAAR6 gene.

Triisopropylamine is an organic chemical compound consisting of three isopropyl groups bound to a central nitrogen atom. As a hindered tertiary amine, it can be used as a non-nucleophilic base and as a stabilizer for polymers; however, its applications are limited by its relatively high cost and difficult synthesis.

<span class="mw-page-title-main">Mammalian reproduction</span> Most mammals are viviparous, giving birth to live young

Most mammals are viviparous, giving birth to live young. However, the five species of monotreme, the platypuses and the echidnas, lay eggs. The monotremes have a sex determination system different from that of most other mammals. In particular, the sex chromosomes of a platypus are more like those of a chicken than those of a therian mammal.

Borane <i>tert</i>-butylamine Chemical compound

Borane tert-butylamine is an amine borane complex derived from tert-butylamine and borane. It is a colorless solid.

<span class="mw-page-title-main">Copulation (zoology)</span> Animal sexual reproductive act in which a male introduces sperm into the females body

In zoology, copulation is animal sexual behavior in which a male introduces sperm into the female's body, especially directly into her reproductive tract. This is an aspect of mating. Many animals that live in water use external fertilization, whereas internal fertilization may have developed from a need to maintain gametes in a liquid medium in the Late Ordovician epoch. Internal fertilization with many vertebrates occurs via cloacal copulation, known as cloacal kiss, while most mammals copulate vaginally, and many basal vertebrates reproduce sexually with external fertilization.

The Hoover-Drickamer effect occurs when adult female mice are exposed to the urine of pregnant and lactating adult female mice, resulting in a longer than typical oestrus period. The effect was first noted by J. E. Hoover and L. C. Drickamer in their 1979 study wherein they randomly assigned adult female mice to one of four treatment conditions: a control group where the subjects were exposed to water, a group that was exposed to the urine of pregnant mice, a group that was exposed to the urine of lactating mice and a group that was exposed to the urine of a singly caged female mouse.

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.