(시사) 경찰이 시위대에 뿌리는 캡사이신(capsaicin)은 무엇인가?

이하 한국어자료 출처: http://ko.wikipedia.org/wiki/%EC%BA%A1%EC%82%AC%EC%9D%B4%EC%8B%A0

경찰이 시위대에 뿌리는 캡사이신(capsaicin)은 무엇인가?

캡사이신

위키백과, 우리 모두의 백과사전.

캡사이신

일반적인 성질
IUPAC 이름	8-Methyl-N-vanillyl-trans-6-nonenamide
CAS 번호	404-86-4
PubChem	1548943
ChemSpider	1265957
물리적 성질
열화학적 성질
안전성

캡사이신(capsaicin, 구조식: (CH₃)₂CHCH=CH(CH₂)₄CONHCH₂C₆H₃-4-(OH)-3-(OCH₃))은 알칼로이드의 하나이다. 고추속 식물의 유효성분 가운데 하나로, 인간을 포함한 포유류에 접촉했을 때 자극을 준다. 캡사이신과 이에 관련된 화합물을 캡사이시노이드(capsaicinoid)라고 부른다.

지용성의 무색의 결정으로 알코올에는 녹기 쉽지만 냉수에는 거의 녹지 않는다. 섭취하면 수용체 활성화 채널의 하나인TRPV1를 자극해, 실제로 온도가 상승하지는 않지만, 격렬한 발열감을 끌어 일으킨다. 이 기구는 멘톨에 의한 냉자극과 같은 반응이며, 또한 통각 신경을 자극하여 국소 자극 작용 혹은 매운 맛을 느끼게 한다. 체내에 흡수된 캡사이신은 뇌에 옮겨져 내장 감각 신경과 반응하여 부신의 아드레날린의 분비를 활발하게 촉진하며, 발한 및 강심 작용을 재촉한다.

고추의 매운 맛을 이끄는 주성분으로, 매운 맛의 국제 표준 지표인 스코빌 척도의 표준 물질이다.

관련 항목[편집]

• 스코빌 척도
• 고추
• 고추장

바깥 링크[편집]

• 캡사이신 기술적 팩스 정보 - 국립 살충 정보 센터
• EPA 캡사이신 등록 적격 결정 확인서
• 캡사이신과 그 치료적 잠재
• Molecule of the Month
• 고추와 캡사이신의 마법
• European Commission, opinion of the Scientific Committee on Food on capsaicin.
• A WikiHow article on How to Cool Chilli Pepper Burns.
• The Neurobiology of Disease wiki, from Connecticut College: Capsaicin

이하 영어자료 출처: http://en.wikipedia.org/wiki/Capsaicin

Capsaicin

From Wikipedia, the free encyclopedia

Capsaicin

Names
IUPAC name (E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Other names 8-Methyl-N-vanillyl-trans-6-nonenamide;trans-8-Methyl-N-vanillylnon-6-enamide; (E)-Capsaicin; Capsicine; Capsicin; CPS
Identifiers
ATC code	M02AB01 N01BX04
CAS Registry Number	404-86-4
ChEBI	CHEBI:3374
ChEMBL	ChEMBL294199
ChemSpider	1265957
EC number	206-969-8
InChI[show]
Jmol-3D images	Image
KEGG	C06866
PubChem	1548943
SMILES[show]
UNII	S07O44R1ZM
Properties
Molecular formula	C18H27NO3
Molar mass	305.41 g·mol−1
Appearance	crystalline white powder[1]
Odor	highly volatile and pungent
Melting point	62 °C (144 °F; 335 K)
Boiling point	210 °C (410 °F; 483 K) 0.01 Torr
Solubility in water	0.0013 g/100 mL
Solubility	soluble in alcohol, ether,benzene slightly soluble in CS2, HCl,petroleum
UV-vis (λmax)	280 nm
Structure
Crystal structure	monoclinic
Hazards
MSDS	Capsaicin, Natural MSDS
Main hazards	Toxic (T)
R-phrases	R24/25
S-phrases	S26, S36/37/39, S45
NFPA 704	1 2 0
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
verify (what is: /?)
Infobox references

Capsaicin

Heat	Above Peak (SR: 15,000,000-16,000,000)

Capsaicin (/kæpˈseɪ.ɨsɪn/; chemical name 8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is an irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related compounds are called capsaicinoids and are produced as secondary metabolites by chili peppers, probably as deterrents against certain mammals and fungi.^[2] Pure capsaicin is avolatile, hydrophobic, colorless, odorless, crystalline to waxy compound.

Contents

  [hide] 

• 1 History
• 2 Capsaicinoids
• 3 Natural function
• 4 Uses
  • 4.1 Food
  • 4.2 Medical
  • 4.3 Non-lethal force
  • 4.4 Pest deterrent
  • 4.5 Equestrian sports
• 5 Mechanism of action
• 6 Toxicity
  • 6.1 Acute health effects
  • 6.2 Treatment after exposure
  • 6.3 Effects of dietary consumption
  • 6.4 Effects on weight loss and regain
• 7 See also
• 8 References
  • 8.1 Footnotes
  • 8.2 General references
• 9 Further reading
• 10 External links

History[edit]

The compound was first extracted in impure form in 1816 by Christian Friedrich Bucholz (1770–1818).^[3] He called it "capsicin", after the genus Capsicum from which it was extracted. John Clough Thresh (1850–1932), who had isolated capsaicin in almost pure form,^[4][5] gave it the name "capsaicin" in 1876.^[6] Karl Micko isolated capsaicin in its pure form in 1898.^[7] Capsaicin's chemical composition was first determined by E. K. Nelson in 1919, who also partially elucidated capsaicin's chemical structure.^[8] Capsaicin was first synthesized in 1930 by E. Spath and S. F. Darling.^[9] In 1961, similar substances were isolated from chili peppers by the Japanese chemists S. Kosuge and Y. Inagaki, who named them capsaicinoids.^[10][11]

In 1873 German pharmacologist Rudolf Buchheim^[12] (1820–1879) and in 1878 the Hungarian doctor Endre Hőgyes^[13] stated that "capsicol" (partially purified capsaicin^[14]) caused the burning feeling when in contact with mucous membranes and increased secretion of gastric acid.

Capsaicinoids[edit]

Capsaicin is the main capsaicinoid in chili peppers, followed by dihydrocapsaicin. These two compounds are also about twice as potent to the taste and nerves as the minor capsaicinoids nordihydrocapsaicin, homodihydrocapsaicin, and homocapsaicin. Dilute solutions of pure capsaicinoids produced different types of pungency; however, these differences were not noted using more concentrated solutions.

Capsaicin is believed to be synthesized in the interlocular septum of chili peppers by addition of a branched-chain fatty acid tovanillylamine; specifically, capsaicin is made from vanillylamine and 8-methyl-6-nonenoyl CoA.^[15][16] Biosynthesis depends on the gene AT3, which resides at the pun1 locus, and which encodes a putative acyltransferase.^[17]

Besides the six natural capsaicinoids, one synthetic member of the capsaicinoid family exists. Vanillylamide of n-nonanoic acid(VNA, also PAVA) is used as a reference substance for determining the relative pungency of capsaicinoids.

Capsaicinoid name	Abbrev.	Typical relative amount	Scoville heat units	Chemical structure
Capsaicin	C	69%	16,000,000
Dihydrocapsaicin	DHC	22%	15,000,000
Nordihydrocapsaicin	NDHC	7%	9,100,000
Homodihydrocapsaicin	HDHC	1%	8,600,000
Homocapsaicin	HC	1%	8,600,000
Nonivamide	PAVA		9,200,000

Natural function[edit]

Capsaicin is present in large quantities in the placental tissue (which holds the seeds), the internal membranes and, to a lesser extent, the other fleshy parts of the fruits of plants in the genus Capsicum. The seeds themselves do not produce any capsaicin, although the highest concentration of capsaicin can be found in the white pith of the inner wall, where the seeds are attached.^[18]

The seeds of Capsicum plants are dispersed predominantly by birds: in birds, the TRPV1 channel does not respond to capsaicin or related chemicals (avian vs mammalian TRPV1 show functional diversity and selective sensitivity). This is advantageous to the plant, as chili pepper seeds consumed by birds pass through the digestive tract and can germinate later, whereas mammals have molar teeth which destroy such seeds and prevent them from germinating. Thus, natural selection may have led to increasing capsaicin production because it makes the plant less likely to be eaten by animals that do not help it reproduce.^[19] There is also evidence that capsaicin may have evolved as an anti-fungal agent:^[20] the fungal pathogen Fusarium, which is known to infect wild chilies and thereby reduce seed viability, is deterred by capsaicin, which thus limits this form of predispersal seed mortality.

In 2006, it was discovered that the venom of a certain tarantula species activates the same pathway of pain as is activated by capsaicin; this was the first demonstrated case of such a shared pathway in both plant and animal anti-mammal defense.^[21]

Uses[edit]

Food[edit]

Because of the burning sensation caused by capsaicin when it comes in contact with mucous membranes, it is commonly used in food products to provide added spice or "heat" (piquancy).^[22] In high concentrations, capsaicin will also cause a burning effect on other sensitive areas, such as skin or eyes.^[23] The degree of heat found within a food is often measured on the Scoville scale.^[22] In some cases, because people enjoy the heat,^[22] there has long been a demand for capsaicin-spiced products like hot sauce orsalsa.^[22]

It is common for people to experience pleasurable and even euphoriant effects from ingesting capsaicin.^[22] Folklore among self-described "chiliheads" attributes this to pain-stimulated release of endorphins, a different mechanism from the local receptor overload that makes capsaicin effective as a topical analgesic.^[23]

Medical[edit]

Capsaicin is used as an analgesic in topical ointments, nasal sprays (Sinol-M), and dermal patches to relieve pain, typically in concentrations between 0.025% and 0.25%. It may be applied in cream form for the temporary relief of minor aches and pains of muscles and joints associated with arthritis, backache, strains and sprains, often in compounds with other rubefacients.^[24] It is also used to reduce the symptoms of peripheral neuropathy such as post-herpetic neuralgia caused by shingles.^[25] In direct application the treatment area is typically numbed first with a topical anesthetic; capsaicin is then applied by a therapist wearing rubber gloves and a face mask. The capsaicin remains on the skin until the patient starts to feel the "heat", at which point it is promptly removed. Capsaicin is also available in large bandages (plasters) that can be applied to the back.

Capsaicin creams are used to treat psoriasis as an effective way to reduce itching and inflammation.^[26][27]

The mechanism by which capsaicin's analgesic and/or anti-inflammatory effects occurs is purportedly by mimicking a burning sensation; overwhelming the nerves by the calcium influx, and thereby rendering the nerves unable to report pain for an extended period of time. With chronic exposure to capsaicin, neurons are depleted ofneurotransmitters, leading to reduction in sensation of pain and blockade of neurogenic inflammation. If capsaicin is removed, the neurons recover.^{[28][29][citation needed]}

Capsaicin selectively binds to a protein known as TRPV1 that resides on the membranes of pain and heat-sensing neurons.^[30][31] TRPV1 is a heat-activated calcium channel that opens between 37 and 45 °C (98.6 and 113 °F, respectively). When capsaicin binds to TRPV1, it causes the channel to open below 37 °C (normal human body temperature), which is why capsaicin is linked to the sensation of heat. Prolonged activation of these neurons by capsaicin depletes presynaptic substance P, one of the body's neurotransmitters for pain and heat. Neurons that do not contain TRPV1 are unaffected.

One study with human subjects indicates that capsaicin may be used to help regulate blood sugar levels by affecting carbohydrate breakdown after a meal.^[32]

Rodent studies have shown that capsicum may have some effectiveness against cancer. However, the American Cancer Society warns "available scientific research does not support claims for the effectiveness of capsicum or whole pepper supplements in preventing or curing cancer at this time".^[33] Other uses not supported by evidence are: "addiction, malaria, yellow fever, heart disease, stroke, weight loss, poor appetite, and sexual potency".^[33]

Capsaicin is the key ingredient in the experimental drug Adlea, which is in (as of 2007) 'Phase 2 Trials' as a long-acting analgesic to treat post-surgical and osteoarthritic pain for weeks to months after a single injection to the site of pain.^[34] Moreover, the drug purportedly reduces pain caused by osteoarthritis,^[35] joint and/or muscle pain fromfibromyalgia and from other causes.

Non-lethal force[edit]

Capsaicin is also the active ingredient in riot control and personal defense pepper spray chemical agents. When the spray comes in contact with skin, especially eyes ormucous membranes, it is very painful, and breathing small particles of it as it disperses can cause breathing difficulty, which serves to discourage assailants. Refer to theScoville scale for a comparison of pepper spray to other sources of capsaicin.

Pest deterrent[edit]

Capsaicin is also used to deter pests, specifically mammalian pests. Targets of capsaicin repellants include voles, deer, rabbits, squirrels, insects, and attacking dogs.^[36] Ground or crushed dried chili pods may be used in birdseed to deter rodents,^[37] taking advantage of the insensitivity of birds to capsaicin. The Elephant Pepper Development Trustclaims the use of chili peppers to improve crop security for rural African communities^{[citation needed]}. Notably, an article published in the Journal of Environmental Science and Health in 2006 states that "Although hot chili pepper extract is commonly used as a component of household and garden insect-repellent formulas, it is not clear that the capsaicinoid elements of the extract are responsible for its repellency."^[38]

The first pesticide product using solely capsaicin as the active ingredient was registered with the U.S. Department of Agriculture in 1962.^[36] There are multiple manufacturers of a capsaicin-based gel product claiming to be a feral-pigeon (Columba livia) deterrent from specific roosting and loafing areas. Some of these products have an EPA label and NSF approval^{[citation needed]}.

Equestrian sports[edit]

Capsaicin is a banned substance in equestrian sports because of its hypersensitizing and pain-relieving properties. At the show jumping events of the 2008 Summer Olympics, four horses tested positive for the substance, which resulted in disqualification.^[39]

Mechanism of action[edit]

The burning and painful sensations associated with capsaicin result from its chemical interaction with sensory neurons. Capsaicin, as a member of the vanilloid family, binds to a receptor called the vanilloid receptor subtype 1 (TRPV1).^[40] First cloned in 1997, TRPV1 is an ion channel-type receptor.^[41] TRPV1, which can also be stimulated with heat, protons and physical abrasion, permits cations to pass through the cell membrane when activated. The resulting depolarization of the neuron stimulates it to signal the brain. By binding to the TRPV1 receptor, the capsaicin molecule produces similar sensations to those of excessive heat or abrasive damage, explaining why the spiciness of capsaicin is described as a burning sensation.

Early research showed capsaicin to evoke a strikingly long-onset current in comparison to other chemical agonists, suggesting the involvement of a significant rate-limiting factor.^[42] Subsequent to this, the TRPV1 ion channel has been shown to be a member of the superfamily of TRP ion channels, and as such is now referred to as TRPV1. There are a number of different TRP ion channels that have been shown to be sensitive to different ranges of temperature and probably are responsible for our range of temperature sensation. Thus, capsaicin does not actually cause a chemical burn, or indeed any direct tissue damage at all, when chili peppers are the source of exposure. The inflammation resulting from exposure to capsaicin is believed to be the result of the body's reaction to nerve excitement. For example, the mode of action of capsaicin in inducing bronchoconstriction is thought to involve stimulation of C fibers^[43] culminating in the release of neuropeptides. In essence, the body inflames tissues as if it has undergone a burn or abrasion and the resulting inflammation can cause tissue damage in cases of extreme exposure, as is the case for many substances that cause the body to trigger an inflammatory response.

Toxicity[edit]

Acute health effects[edit]

Capsaicin is a highly irritant material requiring proper protective goggles, respirators, and proper hazardous material-handling procedures. Capsaicin takes effect upon skin contact (irritant, sensitizer), eye contact (irritant), ingestion, and inhalation (lung irritant, lung sensitizer). The LD₅₀ in mice is 47.2 mg/kg.^[44][45]

Painful exposures to capsaicin-containing peppers are among the most common plant-related exposures presented to poison centers.^{[citation needed]} They cause burning or stinging pain to the skin and, if ingested in large amounts by adults or small amounts by children, can produce nausea, vomiting, abdominal pain, and burning diarrhea. Eye exposure produces intense tearing, pain, conjunctivitis, and blepharospasm.^[46]

When used for weight loss in capsules, there has been a report of heart attack; this was thought to be due to excess sympathetic output.^[47]

Treatment after exposure[edit]

The primary treatment is removal from exposure. Contaminated clothing should be removed and placed in airtight bags to prevent secondary exposure.

For external exposure, bathing the mucous membrane surfaces that have contacted capsaicin with oily compounds such as vegetable oil, paraffin oil, petroleum jelly (Vaseline),creams, or polyethylene glycol is the most effective way to attenuate the associated discomfort;^{[citation needed]} since oil and capsaicin are both hydrophobic hydrocarbons the capsaicin that has not already been absorbed into tissues will be picked up into solution and easily removed. Capsaicin can also be washed off the skin using soap, shampoo, or other detergents. Plain water is ineffective at removing capsaicin,^[44] as are bleach, sodium metabisulfite and topical antacid suspensions.^{[citation needed]} Capsaicin is soluble in alcohol, which can be used to clean contaminated items.^[44]

When capsaicin is ingested, cold milk is an effective way to relieve the burning sensation (due to caseins having a detergent effect on capsaicin^[48]); and room-temperature sugar solution (10%) at 20 °C (68 °F) is almost as effective.^[49] The burning sensation will slowly fade away over several hours if no actions are taken.

Burning and pain symptoms can also be relieved by cooling, such as from ice, cold water, cold bottles, cold surfaces, or a flow of air from wind or a fan.^{[citation needed]} In severe cases, eye burn might be treated symptomatically with topical ophthalmic anesthetics, and mucous membrane burn with lidocaine gel. The gel from the aloe plant has also been shown to be very effective.^{[citation needed]} Capsaicin-induced asthma might be treated with nebulized bronchodilators^{[citation needed]} or oral antihistamines orcorticosteroids.^[46]

Effects of dietary consumption[edit]

Ingestion of spicy food or ground jalapeño peppers does not cause mucosal erosions or other abnormalities.^[50] Some mucosal microbleeding has been found after eating red and black peppers, but there was no significant difference between aspirin (used as a control) and peppers.^[51] The question of whether chili ingestion increases or decreases risk of stomach cancer is mixed: a study of Mexican patients found self-reported capsaicin intake levels associated with increased stomach cancer rates (and this is independent of infection with Helicobacter pylori^[52]) while a study of Italians suggests eating hot peppers regularly was protective against stomach cancer.^[53] Carcinogenic, co-carcinogenic, and anticarcinogenic effects of capsaicin have been reported in animal studies.^[54][55]

Effects on weight loss and regain[edit]

There is no evidence showing that weight loss is directly correlated with ingesting capsaicin, but there is a positive correlation between ingesting capsaicin and a decrease in weight regain. The effects of capsaicin are said to cause "a shift in substrate oxidation from carbohydrate to fat oxidation".^[56] This leads to a decrease in appetite as well as a decrease in food intake.^[56] Even though ingestion of capsaicin causes thermogenesis, the increase in body temperature does not affect weight loss. However, both oral and gastrointestinal exposure to capsaicin increases satiety and reduces energy as well as fat intake.^[57] Oral exposure proves to yield stronger reduction suggesting that capsaicin has sensory effects. Short-term studies suggest that capsaicin aids in the decrease of weight regain. However, long-term studies are limited because of the pungency of capsaicin.^[58] Another recent study has suggested that the ingestion of capsaicinoids can increase energy expenditure and fat oxidation through the activation of brown adipose tissue (BAT) in humans from the effects of the capsaicin.^[59]