Catecholamine

OH
OH
epinephrine (adrenaline)

dihydroxybenzene group.
Catecholamines are derived from the amino acid
tyrosine.[2] Catecholamines are water-soluble and are
50%-bound to plasma proteins when they circulate in the
bloodstream.

Catechol

In the human body, the most abundant catecholamines

are epinephrine (adrenaline), norepinephrine (noradrenaline) and dopamine, all of which are produced from
phenylalanine and tyrosine. Release of the hormones
epinephrine and norepinephrine from the adrenal medulla
of the adrenal glands is part of the ght-or-ight response.[3]
Tyrosine is created from phenylalanine by hydroxylation
by the enzyme phenylalanine hydroxylase.
Tyrosine is also ingested directly from dietary protein.
Catecholamine-secreting cells use several reactions to
convert tyrosine serially to L-DOPA and then to
dopamine. Depending on the cell type, dopamine may
be further converted to norepinephrine or even further
converted to epinephrine.[4]

dopamine

Various stimulant drugs are catecholamine analogues.

1 Structure
Catecholamines have the distinct structure of a benzene
ring with two hydroxyl groups, an intermediate ethyl
chain, and a terminal amine group. Phenylethanolamines
norepinephrine (noradrenaline)
such as norepinephrine have a hydroxyl group on the ethyl
A catecholamine (CA) is a monoamine, an organic com- chain.
pound that has a catechol (benzene with two hydroxyl side
groups) and a side-chain amine.[1]

2 Production and degradation

Catechol is a chemical, but a catechol may also be used

as the name of a substituent, where it represents a 1,21

2.1

2 PRODUCTION AND DEGRADATION

Location

Catecholamines are produced mainly by the chroman

cells of the adrenal medulla and the postganglionic bers
of the sympathetic nervous system. Dopamine, which
acts as a neurotransmitter in the central nervous system,
is largely produced in neuronal cell bodies in two areas
of the brainstem: the substantia nigra and the ventral
tegmental area. The similarly melanin-pigmented cell
bodies of the locus ceruleus produce norepinephrine.

2.2

Synthesis

Dopamine is the rst catecholamine synthesized from

DOPA. In turn, norepinephrine and epinephrine are derived from further metabolic modication of dopamine.
The enzyme dopamine hydroxylase requires copper as a
cofactor (not shown) and DOPA decarboxylase requires
PLP (not shown). The rate limiting step in catecholamine
biosynthesis is hydroxylation of tyrosine.
Human biosynthesis pathway for trace amines and
catecholamines[5]

L-Phenylalanine
L-Tyrosine
L-Dopa
Epinephrine
Phenethylamine
p-Tyramine
Dopamine
Norepinephrine
N-Methylphenethylamine
N-Methyltyramine
p-Octopamine
Synephrine
3-Methoxytyramine
AADC
AADC
AADC
PNMT
PNMT
PNMT

3.2

Eects

PNMT
AAAH
AAAH
COMT
DBH
DBH
L-Phenylalanine is converted into L-tyrosine by the

enzyme Aromatic amino acid hydroxylase (AAAH),

with molecular oxygen (O2 ) and tetrahydrobiopterin
as cofactors. L-Tyrosine is converted into L-DOPA by
the enzyme AAAH with tetrahydrobiopterin, O2 , and
ferrous iron (Fe2+ ) as cofactors. L-DOPA is converted
into dopamine by the enzyme aromatic L-amino acid
decarboxylase (AADC), with pyridoxal phosphate as
the cofactor. Dopamine itself is also used as precursor
in the synthesis of the neurotransmitters norepinephrine
and epinephrine. Dopamine is converted into norepinephrine by the enzyme dopamine -hydroxylase
(DBH), with O2 and L-ascorbic acid as cofactors. Norepinephrine is converted into epinephrine by the enzyme
phenylethanolamine N-methyltransferase (PNMT) with
S-adenosyl-L-methionine as the cofactor.

3
in the brainstem, in particular those nuclei aecting the
sympathetic nervous system. In emergency medicine, this
occurrence is widely known as catecholamine dump.
Extremely high levels of catecholamine can also be
caused by neuroendocrine tumors in the adrenal medulla,
a treatable condition known as pheochromocytoma.
High levels of catecholamines can also be caused by
monoamine oxidase A (MAO-A) deciency. As MAOA is one of the enzymes responsible for degradation
of these neurotransmitters, its deciency increases the
bioavailability of these neurotransmitters considerably. It
occurs in the absence of pheochromocytoma, neuroendocrine tumors, and carcinoid syndrome, but it looks similar to carcinoid syndrome such as facial ushing and
aggression.[8][9]

3.2 Eects

Catecholamines cause general physiological changes that

prepare the body for physical activity (ght-or-ight response). Some typical eects are increases in heart rate,
blood pressure, blood glucose levels, and a general reaction of the sympathetic nervous system. Some drugs, like
Catecholamine synthesis is inhibited by alpha-methyl-p- tolcapone (a central COMT-inhibitor), raise the levels of
all the catecholamines.
tyrosine (AMPT), which inhibits tyrosine hydroxylase.

2.3

Degradation

Catecholamines have a half-life of a few minutes when

circulating in the blood. They can be degraded either by
methylation by catechol-O-methyltransferases (COMT)
or by deamination by monoamine oxidases (MAO).
MAOIs bind to MAO, thereby preventing it from breaking down catecholamines and other monoamines.

3
3.1

Function
Modality

Two catecholamines, norepinephrine and dopamine, act

as neuromodulators in the central nervous system and as
hormones in the blood circulation. The catecholamine
norepinephrine is a neuromodulator of the peripheral
sympathetic nervous system but is also present in the
blood (mostly through spillover from the synapses of
the sympathetic system).

3.3 Function in plants

They have been found in 44 plant families, but no essential metabolic function has
been established for them. They are precursors of benzo[c]phenanthridine alkaloids,
which are the active principal ingredients of
many medicinal plant extracts. CAs have been
implicated to have a possible protective role
against insect predators, injuries, and nitrogen
detoxication. They have been shown to promote plant tissue growth, somatic embryogenesis from in vitro cultures, and owering. CAs
inhibit indole-3-acetic acid oxidation and enhance ethylene biosynthesis. They have also
been shown to enhance synergistically various
eects of gibberellins.[10]

4 See also
Catechol-O-methyl transferase

High catecholamine levels in blood are associated with

stress, which can be induced from psychological reactions
or environmental stressors such as elevated sound levels,
intense light, or low blood sugar levels.

Catecholaminergic polymorphic ventricular tachycardia

Extremely high levels of catecholamines (also known as

catecholamine toxicity) can occur in central nervous system trauma due to stimulation and/or damage of nuclei

Hormone

History of catecholamine research

Julius Axelrod

6
Peptide hormone
Phenethylamines
Steroid hormone
Sympathomimetics
Vanillylmandelic acid

References

[1] Fitzgerald, P. A. (2011). Chapter 11. Adrenal Medulla

and Paraganglia. In Gardner, D. G.; Shoback, D.
Greenspans Basic & Clinical Endocrinology (9th ed.).
New York: McGraw-Hill. Retrieved October 26, 2011.
[2] Purves, D.; Augustine, G. J.; Fitzpatrick, D.; Hall, W.
C.; LaMantia, A. S.; McNamara, J. O.; White, L. E., ed.
(2008). Neuroscience (4th ed.). Sinauer Associates. pp.
1378. ISBN 978-0-87893-697-7.
[3] Catecholamines. Health Library. San Diego: University
of California.
[4] Joh, T. H.; Hwang, O. (1987). Dopamine BetaHydroxylase: Biochemistry and Molecular Biology. Annals of the New York Academy of Sciences 493: 342
350. doi:10.1111/j.1749-6632.1987.tb27217.x. PMID
3473965.
[5]

[6][7]

[6] Broadley KJ (March 2010). The vascular eects of

trace amines and amphetamines. Pharmacol. Ther. 125
(3): 363375. doi:10.1016/j.pharmthera.2009.11.005.
PMID 19948186.
[7] Lindemann L, Hoener MC (May 2005). A renaissance in trace amines inspired by a novel GPCR family. Trends Pharmacol. Sci. 26 (5): 274281.
doi:10.1016/j.tips.2005.03.007. PMID 15860375.
[8] Manor, I.; Tyano, S.; Mel, E.; Eisenberg, J.; BachnerMelman, R.; Kotler, M.; Ebstein, R. P. (2002). FamilyBased and Association Studies of Monoamine Oxidase
A and Attention Decit Hyperactivity Disorder (ADHD):
Preferential Transmission of the Long Promoter-Region
Repeat and its Association with Impaired Performance
on a Continuous Performance Test (TOVA)". Molecular
Psychiatry 7 (6): 626632. doi:10.1038/sj.mp.4001037.
PMID 12140786.
[9] Brunner, H. G. (1996). MAOA Deciency and Abnormal Behaviour: Perspectives on an Association. Ciba
Foundation Symposium 194: 155164; discussion 164
167. PMID 8862875.
[10] Kuklin, A. I.; Conger, B. V. (1995). Catecholamines in
Plants. Journal of Plant Growth Regulation 14 (2): 91
97. doi:10.1007/BF00203119.

EXTERNAL LINKS

6 External links
Catecholamines at the US National Library of
Medicine Medical Subject Headings (MeSH)

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