organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...

, alkanolamines are

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

s that contain both

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

() and

amino In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent ...

(, , and )

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

s on an

alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which ...

backbone. The term alkanolamine is a broad class term that is sometimes used as a subclassification. Methanolamine.svg,

methanolamine Aminomethanol is the amino alcohol with the chemical formula of H2NCH2OH. With an amino group and an alcohol group on the same carbon atom, the compound is also an hemiaminal. In aqueous solution, methanolamine exists in equilibrium with formal ...

, an intermediate in the reaction of ammonia with formaldehyde Ethanolamine.png,

Ethanolamine Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid wit ...

2-amino-2-methyl-1-propanol.svg, 2-amino-2-methyl-1-propanol is a precursor to

oxazoline Oxazoline is a five-membered heterocyclic organic compound with the formula . It is the parent of a family of compounds called oxazolines (emphasis on plural), which contain non-hydrogenic substituents on carbon and/or nitrogen. Oxazolines are the ...

s valinol.svg,

valinol Valinol is an organic compound named after, and commonly produced from, the amino acid valine. The compound is chiral and is produced almost exclusively as the S‑isomer (also designated as the L‑isomer), due to the abundant supply of S-valine. ...

is derived from the amino acid

valine 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 deprotonat ...

Sphingosine structure.svg,

Sphingosine Sphingosine (2-amino-4-trans-octadecene-1,3-diol) is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids, a class of cell membrane lipids that include sphingomyelin, an important phospholip ...

is a component of some

cell membrane The cell membrane (also known as the plasma membrane (PM) or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of all cells from the outside environment ( ...

1-Aminoalcohols

1-Aminoalcohols are better known as

hemiaminal In organic chemistry, a hemiaminal (also carbinolamine) is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: . R can be hydrogen or an alkyl group. Hemiaminals are intermedia ...

Methanolamine Aminomethanol is the amino alcohol with the chemical formula of H2NCH2OH. With an amino group and an alcohol group on the same carbon atom, the compound is also an hemiaminal. In aqueous solution, methanolamine exists in equilibrium with formal ...

is the simplest member.

2-Aminoalcohols

Key members:

ethanolamine Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid wit ...

dimethylethanolamine Dimethylethanolamine (DMAE or DMEA) is an organic compound with the formula (CH3)2NCH2CH2OH. It is bifunctional, containing both a tertiary amine and primary alcohol functional groups. It is a colorless viscous liquid. It is used in skin care prod ...

, ''N''-methylethanolamine,

Aminomethyl propanol Aminomethyl propanol is an organic compound with the formula H2NC(CH3)2CH2OH. It is colorless liquid that is classified as an alkanolamine. It is a useful buffer and a precursor to numerous other organic compounds. Synthesis Aminomethyl propano ...

Two popular drugs, often called alkanolamine

beta blocker Beta blockers, also spelled β-blockers, are a class of medications that are predominantly used to manage cardiac arrhythmia, abnormal heart rhythms, and to protect the heart from a second myocardial infarction, heart attack after a first heart ...

s, are members of this structural class:

propranolol Propranolol, sold under the brand name Inderal among others, is a medication of the beta blocker class. It is used to treat high blood pressure, a number of types of irregular heart rate, thyrotoxicosis, capillary hemangiomas, performance anx ...

pindolol Pindolol, sold under the brand name Visken among others, is a nonselective beta blocker which is used in the treatment of hypertension.Drugs.coInternational brand names for pindolol Page accessed Sept 4, 2015 It is also an antagonist of the se ...

Isoetarine Isoetharine is a selective short-acting β2 adrenoreceptor agonist. It can be called the "granddaughter of adrenalin" in the line of β2 agonists that gave quick relief for bronchospasm and asthma. Epinephrine (adrenalin) was the first of thes ...

is yet another medicinally useful derivative of ethanolamine. 2-Aminoalcohols are an important class of

s that are often generated often by the reaction of amines with

epoxide In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for ...

s. Simple alkanolamines are used as

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

s, synthetic intermediates, and high-boiling bases.

Preparation

Ethylene oxide Ethylene oxide is an organic compound with the chemical formula, formula . It is a cyclic ether and the simplest epoxide: a three-membered Ring (chemistry), ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless a ...

and related epoxides add to amines: : Hydrogenation or hydride reduction of

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha am ...

s gives the corresponding 2-aminoalcohols. Examples include

prolinol Prolinol is a chiral amino-alcohol that is used as a chiral building block in organic synthesis. It exists as two enantiomers: the D and L forms. Preparation Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydri ...

(from

proline Proline (symbol Pro or P) is an organic acid classed as a proteinogenic amino acid (used in the biosynthesis of proteins), although it does not contain the amino group but is rather a secondary amine. The secondary amine nitrogen is in the prot ...

(from

tyrosinol Tyrosinol is an organic compound with the formula . A colorless or white solid, it is produced by the reduction of the amino acid tyrosine with borane dimethylsulfide. The compound, which is chiral, is an example of a 1,2-ethanolamine. Related c ...

(from

tyrosine -Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid with a polar side group. The word "tyrosine" is from the Gr ...

1,3-, 1,4-, and 1,5-amino alcohols

Heptaminol Heptaminol is an amino alcohol which is classified as a cardiac stimulant (positive inotropic action). It also increases coronary blood flow along with mild peripheral vasoconstriction. It is sometimes used in the treatment of low blood pressure, ...

, a cardiac stimulant *

Propanolamine In organic chemistry, propanolamine can describe any of the following Parent structure, parent compounds: *2-Amino-1-propanol, the hydrogenated derivative of alanine. *3-Amino-1-propanol, straight-chain and not widely used. *3-Amino-2-propanol (1- ...

Natural products

Most

protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, respo ...

s and

peptide Peptides (, ) are short chains of amino acids linked by peptide bonds. Long chains of amino acids are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides. A ...

s contain both alcohols and amino groups. Two amino acids are alkanolamines, formally speaking:

serine Serine (symbol Ser or S) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated − form under biological conditions), a carboxyl group (which is in the deprotonated − form un ...

and

hydroxyproline (2''S'',4''R'')-4-Hydroxyproline, or L-hydroxyproline ( C5 H9 O3 N), is an amino acid, abbreviated as Hyp or O, ''e.g.'', in Protein Data Bank. Structure and discovery In 1902, Hermann Emil Fischer isolated hydroxyproline from hydrolyzed gelatin. ...

. *

Veratridine Veratridine is a steroidal alkaloid found in plants of the lily family, specifically the genera ''Veratrum'' and ''Schoenocaulon''. Upon absorption through the skin or mucous membranes, it acts as a neurotoxin by binding to and preventing the inac ...

and

veratrine Veratridine is a steroidal alkaloid found in plants of the lily family, specifically the genera ''Veratrum'' and ''Schoenocaulon''. Upon absorption through the skin or mucous membranes, it acts as a neurotoxin by binding to and preventing the ina ...

Tropane alkaloid Tropane alkaloids are a class of bicyclic .2.1alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkal ...

s such as

atropine Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given i ...

hormone A hormone (from the Greek participle , "setting in motion") is a class of signaling molecules in multicellular organisms that are sent to distant organs by complex biological processes to regulate physiology and behavior. Hormones are required ...

s and

neurotransmitter A neurotransmitter is a signaling molecule secreted by a neuron to affect another cell across a synapse. The cell receiving the signal, any main body part or target cell, may be another neuron, but could also be a gland or muscle cell. Neuro ...

epinephrine Adrenaline, also known as epinephrine, is a hormone and medication which is involved in regulating visceral functions (e.g., respiration). It appears as a white microcrystalline granule. Adrenaline is normally produced by the adrenal glands and ...

(adrenaline) and

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic chemical in the catecholamine family that functions in the brain and body as both a hormone and neurotransmitter. The name "noradrenaline" (from Latin '' ad'', ...

(noradrenaline)

References

External links

* {{Authority control Alcohols Amines