WATER SOLUBLE VITAMINSThe common features to most of vitamin B complex have been outlined below:-•Cannot be stored in body...
The B vitamins(water soluble vitamins) may be necessary in order to:• Support and increase the rate of metabolism.• Mainta...
Vitamin B1(thiamine )Vitamin B1; antiberi-beri vitamin; antineuritic factorwas the first water soluble vitamin discovered ...
• Structure and chemistry of vitamin B1(Thiamine)• Thiamine consists of a thiazole and pyrimidine ring that are linked thr...
• Christiaan Eijkman had decided he wanted to become a doctor. When the timecame, his family couldnt afford to send him to...
• Eijkman had seen many victims of beriberi while working for the army in theDutch East Indies.• The disease started with ...
• He thought that the skin, which had been removed from the white rice, containeda substance that made the poisonous rice ...
• People found the polished rice from the new milling machines superior in taste, and they chose it overbrown rice even if...
Fortified grain items such as cereals,bread, pasta, rice and tortillas provide themost important sources of thiamine in th...
Dosage RecommendationsThe exact amount of vitamin B needed is unknown; however, onestudy found that healthy people intake ...
• Physiological importance (Role) of vitaminB1:• The active form of vitamin B1 in the body is thiamin pyrophosphate (TPP) ...
• A deficiency in thiamine can cause enlargement of the heart, which can itself lead tocongestive heart failure, and lung ...
• 1.Polyneuritis:In birds polyneuritis results muscular paralysis which results in an inabilityto fly,walk or even stand.I...
• 4.Wernicks encephalopathy(cerebral Beriberi):• It occurs due to severe deficiency of thiamine and is manifested by perip...
Synthesis of vitamin B14-amino-5-bromomethyl-2-methylpyrimidine hydro chloride.5-(β-hydroxyethyl)-4-methyl thiazole. Bromi...
K3Fe(CN)6Oxidation(Fluorescence)Thiamine oxidizes to thiochrone in the presence of oxidizing agents like H2O2,Kmn04 (or) a...
Thiamin helps break downsugars, carbohydrates andfats in the body to provideenergy. Vitamin B1 also helpssupport a normal ...
VITAMIN B1 [THIAMINE] MEDICINAL CHEMISTRY BY P. RAVISANKAR [ SOURCE, STRUCTURES  AND CHEMISTRY OF VITAMIN B1, HYSTORY OF V...
VITAMIN B1 [THIAMINE] MEDICINAL CHEMISTRY BY P. RAVISANKAR [ SOURCE, STRUCTURES  AND CHEMISTRY OF VITAMIN B1, HYSTORY OF V...
VITAMIN B1 [THIAMINE] MEDICINAL CHEMISTRY BY P. RAVISANKAR [ SOURCE, STRUCTURES  AND CHEMISTRY OF VITAMIN B1, HYSTORY OF V...
Upcoming SlideShare
Loading in …5
×

VITAMIN B1 [THIAMINE] MEDICINAL CHEMISTRY BY P. RAVISANKAR [ SOURCE, STRUCTURES AND CHEMISTRY OF VITAMIN B1, HYSTORY OF VITAMIN B1, SOURCES OF VITAMIN B1, RDA, PHYSIOLOGICAL IMPORTANCE(ROLE) OF VITAMIN B1, SYNTHESIS OF VITAMIN B1, OXIDATION OF THIAMINE T

5,892 views

Published on

VITAMIN B1 [THIAMINE] MEDICINAL CHEMISTRY BY P. RAVISANKAR [ SOURCE, STRUCTURES AND CHEMISTRY OF VITAMIN B1, HYSTORY OF VITAMIN B1, SOURCES OF VITAMIN B1, RDA, PHYSIOLOGICAL IMPORTANCE(ROLE) OF VITAMIN B1, SYNTHESIS OF VITAMIN B1, OXIDATION OF THIAMINE TO THIOCROME, THERAPEUTIC USES ,DEFICIENCY OF VITAMIN B1.
BY P.RAVISANKAR
VIGNAN PHARMACY COLLEGE, VADLAMUDI, GUNTUR, A.P, INDIA.

Published in: Education, Health & Medicine
0 Comments
26 Likes
Statistics
Notes
  • Be the first to comment

No Downloads
Views
Total views
5,892
On SlideShare
0
From Embeds
0
Number of Embeds
21
Actions
Shares
0
Downloads
0
Comments
0
Likes
26
Embeds 0
No embeds

No notes for slide

VITAMIN B1 [THIAMINE] MEDICINAL CHEMISTRY BY P. RAVISANKAR [ SOURCE, STRUCTURES AND CHEMISTRY OF VITAMIN B1, HYSTORY OF VITAMIN B1, SOURCES OF VITAMIN B1, RDA, PHYSIOLOGICAL IMPORTANCE(ROLE) OF VITAMIN B1, SYNTHESIS OF VITAMIN B1, OXIDATION OF THIAMINE T

  1. 1. WATER SOLUBLE VITAMINSThe common features to most of vitamin B complex have been outlined below:-•Cannot be stored in body - regular supply needed.•most play an essential role in metabolism.•Most of them can be sourced from liver and yeast.•Most of them are synthesized by colonal bactera.•Excess is excreted in urine(easily to be discharged through urine) - nodanger of toxic levels.•not easy to be stored in the body,requiring diet inception.•Unstable to heat and light, leach into cooking liquids.•ClassificationVitamin B familyVitamin B1 (thiamine), Vitamin B2 (riboflavin).Vitamin B3 (niacin or niacinamide, sometimes also known as vitamin PP).Vitamin B5 (pantothenic acid).Vitamin B6 (pyridoxine, pyridoxal, or pyridoxamine, or pyridoxine hydrochloride).Vitamin B7 (biotin), Vitamin B8 (inositol),Vitamin B9 (folic acid).Vitamin B12 (various cobalamins; commonly cyanocobalamin in vitaminsupplements).Prof. RavisankarVignan Pharmacy collValdlamudiGuntur Dist.Andhra PradeshIndia.banuman35@gmail.co00919059994000Vitamin B1(Thiamine) (aneurin)
  2. 2. The B vitamins(water soluble vitamins) may be necessary in order to:• Support and increase the rate of metabolism.• Maintain healthy skin and muscle tone.• Enhance immune and nervous system function.• Promote cell growth and division, including that of the red blood cells that helpprevent anemia.• Reduce the risk of pancreatic cancer.• Vitamin B1 is needed to help convert the carbohydrates we eat into glucose• The Vitamin B Complex is essential for the healthy functioning of the nervous system• The Vitamin B Complex is essential for correct digestion, production of HCl (Hydrochloricacid) and to assist in the breakdown of fats, proteins and carbohydrates.• Healthy Skin, Hair and Nails• The Vitamin B Complex is essential for correct RNA and DNA synthesis and cellreproduction. Deficiencies of any of these B Vitamins can lead to dry,grey skin, dermatitis, wrinkles, acne, rashes, falling hair and weak,splitting nails.• Thiamin is a water-soluble B-complex vitamin. It was the first Bvitamin to be identified and one of the first organic compounds to berecognised as a vitamin in the 1930s. In fact it was through thediscovery and naming of thiamin that the word vitamin, from theLatin “vita” = life and “amine” = nitrogen-containingcompound, was coined.
  3. 3. Vitamin B1(thiamine )Vitamin B1; antiberi-beri vitamin; antineuritic factorwas the first water soluble vitamin discovered (Eijkman)﹡vitamin B1: thiamine﹡active form :Thiamine pyrophosphate(TPP):Thiamine is one member of water-soluble vitamin B-complexand is in the thermolabile fraction.In the absence of thiamine which is the cause of beriberiin man.Thus this vitamin is the antineuritic factor (hence the nameaneurin)Rice polishings and yeast have been the usual sources of thiamine.
  4. 4. • Structure and chemistry of vitamin B1(Thiamine)• Thiamine consists of a thiazole and pyrimidine ring that are linked through amethylene group.• Thiamine is the only natural compound (apart from penicillin) that contains athiazole ring.112131415161123 45PyrimidineThiazoleMethylene bridge(linkage)(Vitamin B1)CHDissociable protonReactive carbon atom3-[(4-amino-2methyl pyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl thiazolium.Physico-Chemical Properties:Thiamine is white,crystalline powder and slight,characteristic yeast-like odour.It is freely soluble in water and slightly soluble in CHCl3 and ether.It is stable in acid but unstable in aqueous solutions (pH >5) due to
  5. 5. • Christiaan Eijkman had decided he wanted to become a doctor. When the timecame, his family couldnt afford to send him to medical school.• The Dutch colonial ( Indonesia was a Dutch colony) army had use for manydoctors and they paid for his education in exchange.• Christiaan got his medical training, and then went to the colonies to work as an army• surgeonA short time after his arrival he got malaria, and after two years, it becameimpossible for him to work. He was sent back home to recover. Back in Europe andagain he went to Berlin in Germany to study the latest groundbreaking medicalresearchChristiaan Eijkman wasborn on August 11, 1858 inthe Dutch town of Nijkerk.He was the seventh child ofthe headmaster at the localschool.Robert Koch was Eijkmans teacher inBerlin in 1885. Twenty years later, Koch wasto receive the Nobel Prize in Physiology orMedicine for his research
  6. 6. • Eijkman had seen many victims of beriberi while working for the army in theDutch East Indies.• The disease started with signs of weakness, fatigue, irritability, restlessness,loss of appetite and vague abdominal discomfort.• As it progressed, patients developed burning sensations, tingling in the extremities,and changes in the sensation such as numbness. Many of the sufferers died of heartfailure.• Eijkmans Trials; Monkeys, Chickens.• The man who fed the chickens told Eijkman that he had given them cooked white riceduring the period they got sick. It was leftover rice from the next-door hospital. Later,a new cook there didnt want to give him left over rice and he had gone back tofeeding them with unpolished uncooked rice. It was after this that the chickenshad recovered.• When Eijkman understood that the disease had something to do with the diet, hedecided to make trials. He did something like this...• After five weeks, it was clear to Eijkman that the diet did indeed cause the disease.He gave all the chickens unpolished uncooked rice, and the four sick chickensgot well again.
  7. 7. • He thought that the skin, which had been removed from the white rice, containeda substance that made the poisonous rice innocuous. Eijkman called this theanti-beriberi factor.• Brown rice has its outer husk removed.White rice is polished further to removethe thin skin and the germ.• Since the germ is ground off from the white rice grains, they have a slightlypointed appearance.• In 1895, after nine years of research with animals, Eijkman wanted to find out ifhumans could avoid getting beriberi by eating unpolished rice.Because it is water soluble, B1 is not stored in thebody and must be supplied daily. Chickpeas, beans,lentils, brown rice, lean pork and peas are all goodsources of vitamin B1
  8. 8. • People found the polished rice from the new milling machines superior in taste, and they chose it overbrown rice even if it was more expensive.• Christiaan Eijkman was awarded the Nobel Prize in Physiology or Medicine in1929. Due to bad health, he couldnt come to Sweden to receive the Prize. Hedied a year later.One may wonder why Eijkman was awarded the Prize for the discoved vitaminB1 even if he himself didnt discover it.Eijkman was actually awarded the Prize because he was the first to point out asubstance in the rice skin - a substance not to be known as the anti-beriberifactor as Eijkman called it, but what later was to be known as vitamin B1.He was also awarded the Prize for his new way of investigating and his methods tocontrol diseases caused by vitamin deficiency. His trials had become famous.
  9. 9. Fortified grain items such as cereals,bread, pasta, rice and tortillas provide themost important sources of thiamine in thehuman diet. Additionally, lean meats,fish, sunflower seeds, peas andlegumes are extremely rich in thiamine.Dairy products, fruits, and vegetables aretypically not ideal sources of vitamin B1sources of vitaminB1(thiamine)milk,egg yolks,pork,liver,heart,kidneys,yeast contamin thiamine asthiamine pyrophosphate ,broccoli,beanssweet corn,brown rice.polished cereals and folur containalmost no thiamine,Thermolabile vitamin-- Gets destroyed byheat in both alkaline and neutral media. Discarding the water in which the food wascooked also reduces the thiamine content in the cooked food.
  10. 10. Dosage RecommendationsThe exact amount of vitamin B needed is unknown; however, onestudy found that healthy people intake over 9 mg daily. Multivitaminsupplements contain 20-25 mg, which is more than needed by mostpeople.(developing chaild in to adult)
  11. 11. • Physiological importance (Role) of vitaminB1:• The active form of vitamin B1 in the body is thiamin pyrophosphate (TPP) whichalong with lipoic acid acts as a prosthetic group for carboxylases.• Thiamine pyrophosphate is formed by the esterification of alcoholic group ofthiamine with phosphate.TPP transferase catalyzes the transfer of pyrophosphategroup from ATP to thiamine.• Citric acid cycle and synthesis of acetylcholine thus affecting the neurotransmittertransmission. Transketolation reaction and decarboxylation of α-ketoglutaric acid tosuccinic acid.NNCH3CH2NH2SCHN+CH3CH2 CH2 O POHOO POOHOHEsterificationATP AMPTPP transferaseNH2Thiamine pyrophosphate
  12. 12. • A deficiency in thiamine can cause enlargement of the heart, which can itself lead tocongestive heart failure, and lung congestion. A severe deficiency in Vitamin B1 can leadto nerve damage, brain damage and even death. Mental symptoms associated with aserious lack of Vitamin B include fatigue, psychosis, and confusion.These are a few serious diseases specifically associated with a deficiency of Vitamin B1,including the notorious beriberi disease. There are also two specific types of braindamage associated with severely low levels of Vitamin B1. One, Korsakoff syndrome,results in confusion and short term memory loss. Another, Wernicke’s Disease(impairedsensoryperception) has symptoms that include vision disturbances and irregularities, anunsteady walk, and mental confusion.Symptoms include pain,numbness and tingling in theextremities, muscle weaknessand a lack of physicalcoordination, particularly in thelarger muscle masses that makeup the leg musclesedema,(swelling of bodilytissues)irregular heart beat.amnesia,confabulation.Heart failure and death mayoccur in advanced cases.
  13. 13. • 1.Polyneuritis:In birds polyneuritis results muscular paralysis which results in an inabilityto fly,walk or even stand.Increased influx of pyruvic acid in the brain due to impaired functioning of theBlood brain barrier.2. Beriberi caused due to deficiency of Vitamin B1 --- individuals who consumepolished or refined rice gets beri beri.Alcoholics -- genarally retards the absorption of the vitamin.symptoms: weakness irritable nature,depression,drowsiness ,loss ofsleep,appetite ,nausea,abdominal discomfort.Eventual symptos: peripheral neuritis,cramping of leg muscles ,psychologicaldistrubances,CHF.Depending upon the symptoms beriberi it classified in to 4 types.1.Dry Beriberi: peripherial neuritis,muscular atrophy,numbness,burning sensationof legs.wasting of muscles,paralysis in children ,tachycardia.2.Wet beriberi: vomiting,waxyskin,albuminuria and casts in urine.3. Acute pernicious beriberi: leasions in cardiac tissue,peripheral nerves and skincardiomegaly,edematous legs , finally death results due to cardiac failure.
  14. 14. • 4.Wernicks encephalopathy(cerebral Beriberi):• It occurs due to severe deficiency of thiamine and is manifested by peripheralneuropathy,mental confusion paralysis of eye muscles,unsteady gait etc.• The cardiovascular and gastrointestinal symptoms can be ameliorated or ratherreversed with the administration of thiamine.The reversal of neurological damage becomes very bleak incase of severe orprolonged deficiency of the thiamine.Adverse effects:Using thiamine 5mg day for 4-5 weeks leads to headache,isomnia,irritability,increased heartrate,weakness, Injections of thiamine lead to anaphylacticreactions.Dry Beri-beriWet Beri-beri.
  15. 15. Synthesis of vitamin B14-amino-5-bromomethyl-2-methylpyrimidine hydro chloride.5-(β-hydroxyethyl)-4-methyl thiazole. Bromide saltThiamine hydrochloride.
  16. 16. K3Fe(CN)6Oxidation(Fluorescence)Thiamine oxidizes to thiochrone in the presence of oxidizing agents like H2O2,Kmn04 (or) alkaline potassium ferricyanide (or) on exposure to atomsphere.Thiochrome emits a blue fluorescence.Excite thiochrome at 365 nm and measure the absorbance at 435 nmBlue fluorescenceThe oxidation of thiamine to thiochrome
  17. 17. Thiamin helps break downsugars, carbohydrates andfats in the body to provideenergy. Vitamin B1 also helpssupport a normal appetite,maintains a healthynervous system as well asaiding the proper function ofthe heart and other muscles.Vitamin B1 has been usedfor conditions including:Anemia (offers probablehealth benefit)Alzheimer’s DiseaseCanker SoresHepatitisLower back painused in the prophylaxis or treatment of diseaseslike alcoholic neuritis.cardiovascular diseases and GIT symptoms.treatment of Beri-beri.If breast-fed infant is suffering from beriberi ---Mother should be given ----50mg daily dose.infants --- 10 mg.Therapeutic usesRequired to make energy.Prevents the disease beri-beri i.e. nerve damage,paralysis, heart failure.Vitamin B1, also called thiamin, isimportant to blood circulation,metabolism, and brain function.Because of its antioxidant powers.

×