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Anatabine (uh-nat-uh-been,-bin) is one of the minor
alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...
s found in plants in the family
Solanaceae Solanaceae (), commonly known as the nightshades, is a family of flowering plants in the order Solanales. It contains approximately 2,700 species, several of which are used as agricultural crops, medicinal plants, and ornamental plants. Many me ...
, which includes the tobacco plant and
tomato The tomato (, ), ''Solanum lycopersicum'', is a plant whose fruit is an edible Berry (botany), berry that is eaten as a vegetable. The tomato is a member of the nightshade family that includes tobacco, potato, and chili peppers. It originate ...
. Commercial tobacco plants typically produce alkaloids at levels between 2% and 4% of total dry weight, with
nicotine Nicotine is a natural product, naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreational drug use, recreationally as a stimulant and anxiolytic. As ...
accounting for about 90% of the total alkaloid content, and the related compounds anatabine,
nornicotine Nornicotine is an alkaloid found in various plants including ''Nicotiana'', the tobacco plant. It is chemically similar to nicotine, but does not contain a methyl group. It is a precursor to the carcinogen N-Nitrosonornicotine, ''N''-nitrosonorni ...
, and
anabasine Anabasine is a pyridine and piperidine alkaloid found in the tree tobacco ('' Nicotiana glauca'') plant, as well as in tree tobacco's close relative the common tobacco plant ('' Nicotiana tabacum''). It is a structural isomer of, and chemically ...
making up nearly all the rest. These compounds are thought to be biologically active, and part of plants' natural defense system against insects. Anatabine has
anti-inflammatory Anti-inflammatory is the property of a substance or treatment that reduces inflammation, fever or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs reduce pain by inhibiting mechan ...
activity partly through inhibition of
STAT3 Signal transducer and activator of transcription 3 (STAT3) is a transcription factor which in humans is encoded by the ''STAT3'' gene. It is a member of the STAT protein family. Function STAT3 is a member of the STAT protein family. In respon ...
phosphorylation in vitro and in vivo.


Pharmacology

On a
biochemical Biochemistry, or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology, ...
level, it appears to be active against certain
nicotinic acetylcholine receptors Nicotinic acetylcholine receptors, or nAChRs, are receptor polypeptides that respond to the neurotransmitter acetylcholine. Nicotinic receptors also respond to drugs such as the agonist nicotine. They are found in the central and peripheral ner ...
.


Commercial development

Star Scientific developed and sold the compound as a
dietary supplement A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...
primarily through GNC up until mid 2014. Subsequently, Rock Creek Pharmaceuticals (formerly a subsidiary of Star Scientific), headquartered in Florida, began developing anatabine as a
drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...
. The dietary supplements were known as Anatabloc and CigRx; the company has also marketed cosmetics with the Anatabloc brand. Rock Creek had been working on synthetic methods to scale up production of anatabine and has funded pre-clinical and clinical research in several indications. In 2013 the FDA warned Star Scientific for unlawfully promoting CigRx and Anatabloc before anatabine was proved to be safe. Subsequently, new management and a mostly new board under the banner of Rock Creek Pharmaceuticals withdrew the dietary supplement because of the FDA's concerns. In 2013, Star Scientific became embroiled in political scandal, when news broke that the governor of Virginia,
Bob McDonnell Robert Francis McDonnell (born June 15, 1954) is an American politician, attorney, businessman, academic administrator, and former military officer who served as the 71st governor of Virginia from 2010 to 2014. He is a member of the Republica ...
, and his wife had received significant loans and gifts from Jonnie Williams Sr, the CEO of the company. They were found to have helped the company in several ways like arranging meetings with top officials and giving special favors from the state government. Williams resigned in 2014 and the company changed its name and restructured its board and management at the end of 2013 due to the scandal. However, the accumulated legal costs from the defense of Jonnie Williams in the McDonnell scandal overwhelmed the company’s finances and it filed for bankruptcy in 2016. As a consequence, the development and clinical trials of anatabine were halted indefinitely.


Research

Anatabine has been studied in animal models and in cells to see if it might be useful for treating
nicotine addiction Nicotine is a naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and '' Duboisia hopwoodii'') and is widely used recreationally as a stimulant and anxiolytic. As a pharmaceutical drug, it is used fo ...
and
inflammation Inflammation (from ) is part of the biological response of body tissues to harmful stimuli, such as pathogens, damaged cells, or irritants. The five cardinal signs are heat, pain, redness, swelling, and loss of function (Latin ''calor'', '' ...
, and has been studied in models of diseases characterized by inflammation, such as
Alzheimer's disease Alzheimer's disease (AD) is a neurodegenerative disease and the cause of 60–70% of cases of dementia. The most common early symptom is difficulty in remembering recent events. As the disease advances, symptoms can include problems wit ...
,
thyroiditis Thyroiditis is the inflammation of the thyroid gland. The thyroid gland is located on the front of the neck below the laryngeal prominence, and makes hormones that control metabolism. Thyroiditis is a group of disorders that all cause thyroi ...
, and
multiple sclerosis Multiple sclerosis (MS) is an autoimmune disease resulting in damage to myelinthe insulating covers of nerve cellsin the brain and spinal cord. As a demyelinating disease, MS disrupts the nervous system's ability to Action potential, transmit ...
. Note: content is supported by discussion section which provides a brief review of research to date. Anatabine cream was helpful in managing mild to moderate
rosacea Rosacea is a long-term skin condition that typically affects the face. It results in redness, pimples, swelling, and small and superficial dilated blood vessels. Often, the nose, cheeks, forehead, and chin are most involved. A red, en ...
. An internet based survey showed 82% users reported a benefit from anatabine supplementation for one or more joint pain conditions.


See also

* Anatalline *
Anabaseine Anabaseine (3,4,5,6-tetrahydro-2,3′-bipyridine) is an alkaloid toxin produced by ''Nemertines'' worms and ''Aphaenogaster'' ants. It is structurally similar to nicotine and anabasine. Similarly, it has been shown to act as an agonist on most ni ...
* Myosmine


References

{{Reflist, 2 Pyridine alkaloids Alkaloids found in Solanaceae 3-Pyridyl compounds