Oleamide
Encyclopedia
Oleamide is an amide
of the fatty acid
oleic acid
. It is an endogenous
substance: it occurs naturally in the body of animals. It accumulates in the cerebrospinal fluid
during sleep deprivation
and induces sleep in animals. It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression.
The mechanism of action
of oleamide's sleep inducing effects is an area of current research. It is likely that oleamide interacts with multiple neurotransmitter
systems. Oleamide is structurally related to the endogenous cannabinoid anandamide
, and has the ability to bind to the CB1 receptor as a full agonist. In addition, oleamide potentiates several serotonin receptors and the GABA(A) receptor, and inhibits gap junction communication.
Synthetically produced oleamide has a variety of industrial uses including as a slip agent, a lubricant
, and a corrosion inhibitor.
Oleamide was originally characterized as an endogenous bioactive substance, isolated from the cerebrospinal fluid
of sleep deprived cats. It was characterised in 1995 by Benjamin Cravatt III
and Richard Lerner
at The Scripps Research Institute
in La Jolla, CA .
Oleamide was found by researchers to be leaking out of polypropylene
plastics used in laboratory experiments, affecting experimental results. Since polypropylene is used in a wide number of food containers such as those for yogurt, the problem is being studied.
Amide
In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...
of the fatty acid
Fatty acid
In chemistry, especially biochemistry, a fatty acid is a carboxylic acid with a long unbranched aliphatic tail , which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually derived from...
oleic acid
Oleic acid
Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable fats. It has the formula CH37CH=CH7COOH. It is an odorless, colourless oil, although commercial samples may be yellowish. The trans isomer of oleic acid is called elaidic acid...
. It is an endogenous
Endogenous
Endogenous substances are those that originate from within an organism, tissue, or cell. Endogenous retroviruses are caused by ancient infections of germ cells in humans, mammals and other vertebrates...
substance: it occurs naturally in the body of animals. It accumulates in the cerebrospinal fluid
Cerebrospinal fluid
Cerebrospinal fluid , Liquor cerebrospinalis, is a clear, colorless, bodily fluid, that occupies the subarachnoid space and the ventricular system around and inside the brain and spinal cord...
during sleep deprivation
Sleep deprivation
Sleep deprivation is the condition of not having enough sleep; it can be either chronic or acute. A chronic sleep-restricted state can cause fatigue, daytime sleepiness, clumsiness and weight loss or weight gain. It adversely affects the brain and cognitive function. Few studies have compared the...
and induces sleep in animals. It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression.
The mechanism of action
Mechanism of action
In pharmacology, the term mechanism of action refers to the specific biochemical interaction through which a drug substance produces its pharmacological effect...
of oleamide's sleep inducing effects is an area of current research. It is likely that oleamide interacts with multiple neurotransmitter
Neurotransmitter
Neurotransmitters are endogenous chemicals that transmit signals from a neuron to a target cell across a synapse. Neurotransmitters are packaged into synaptic vesicles clustered beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to...
systems. Oleamide is structurally related to the endogenous cannabinoid anandamide
Anandamide
Anandamide, also known as N-arachidonoylethanolamide or AEA, is an endogenous cannabinoid neurotransmitter. The name is taken from the Sanskrit word ananda, which means "bliss, delight", and amide. It is synthesized from N-arachidonoyl phosphatidylethanolamine by multiple pathways...
, and has the ability to bind to the CB1 receptor as a full agonist. In addition, oleamide potentiates several serotonin receptors and the GABA(A) receptor, and inhibits gap junction communication.
Synthetically produced oleamide has a variety of industrial uses including as a slip agent, a lubricant
Lubricant
A lubricant is a substance introduced to reduce friction between moving surfaces. It may also have the function of transporting foreign particles and of distributing heat...
, and a corrosion inhibitor.
Oleamide was originally characterized as an endogenous bioactive substance, isolated from the cerebrospinal fluid
Cerebrospinal fluid
Cerebrospinal fluid , Liquor cerebrospinalis, is a clear, colorless, bodily fluid, that occupies the subarachnoid space and the ventricular system around and inside the brain and spinal cord...
of sleep deprived cats. It was characterised in 1995 by Benjamin Cravatt III
Benjamin Cravatt III
Benjamin Franklin Cravatt is a professor in and chair of the Department of Chemical Physiology at The Scripps Research Institute in La Jolla, California...
and Richard Lerner
Richard Lerner
Richard A. Lerner is an American research chemist. Best known for his work on catalytic antibodies, Lerner is currently President of The Scripps Research Institute , and a member of its Skaggs Institute for Chemical Biology, in La Jolla, California.-Biography:Lerner grew up in Chicago and...
at The Scripps Research Institute
The Scripps Research Institute
The Scripps Research Institute is an American medical research facility that focuses on research in the basic biomedical sciences. Headquartered in La Jolla, California, with a sister facility in Jupiter, Florida, the institute is home to 3,000 scientists, technicians, graduate students, and...
in La Jolla, CA .
Oleamide was found by researchers to be leaking out of polypropylene
Polypropylene
Polypropylene , also known as polypropene, is a thermoplastic polymer used in a wide variety of applications including packaging, textiles , stationery, plastic parts and reusable containers of various types, laboratory equipment, loudspeakers, automotive components, and polymer banknotes...
plastics used in laboratory experiments, affecting experimental results. Since polypropylene is used in a wide number of food containers such as those for yogurt, the problem is being studied.