PCOG LAB - ALKALOIDS

WILHELM MEISSNER

German scientist who coined the term Alkaloid

AL-GALI

the word alkaloid came from the word = substance that has been roasted from ashes / ashes of plants

AL-QALI

the word alkaloid came from the Arabic word ___ = plant from which soda / sodium carbonate was first isolated

ALKALOIDS

• are basic nitrogenous compounds contain one or more nitrogen in heterocyclic ring system having marked physiological action on humans and animals

ALKALI-LIKE

alkaloid is said to be _ because it behave like basic substance (present in heterocyclic ring / walang ring basta may nitrogen present) and acts as inorganic bases (they form salts when reacted with acids)

CRYSTALLINE SOLIDS

most alkaloids are ___, but some are liquids

NICOTINE, CONIINE, SPARTEINE

liquid alkaloids

NICOTINE

isolated from the leaves of tobacco

NICOTIANA TABACUM

scientific name of the plant where nicotine is isolated from

CONIINE

isolated from poison hemlock and dog parsley

CONIIUM MACULATUM

Plant source of coniine, known as poison hemlock.

AETHUSA CYNAPIUM

plant source of coniine, known as dog parsley

SPARTEINE

isolated from common broom / scotch broom and tarwi

CYSTISUS SCOPARIUS

plant source of sparteine; common broom

LUPINUS MUTABILIS

plant source of sparteine; tarwi

PILOCARPINE

• a non-volatile alkaloid that is used for relaxing muscle spasms and for eye conditions like glaucoma
• also used for Xerostomia

XEROSTOMIA

dry mouth; treatment: pilocarpine

HYOSCINE

a non-volatile alkaloid that is used for nausea and vomiting associated with motion sickness

SCOPOLAMINE

another name for hyoscine

PILOCARPUS JABORANDI

scientific name for Pilocarpine

BERBERINE

colored alkaloid that has a bright crystal yellow color

BERBERIS VULGARIS

scientific name of common barberry

COMMON BARBERRY

common name where the colored alkaloid berberine is isolated from

ALCOHOL

(solubility of alkaloids) both alkaloidal bases and their salts are soluble in _

ALKALOIDAL BASES

(solubility of alkaloids); generally,__are soluble in organic solvents

ALKALOIDAL SALTS

(solubility of alkaloids); ____ are soluble in water

SALTS

due to the basic characteristic of alkaloids, they react with acids to form _

MORPHINE AND CODEINE

2 well known drugs that forms salts because of its basic character

AMPHOTERICITY

chemical property of alkaloids which it can form salts with both acids and alkalis

MORPHINE

phenolic group () - phenol: weakly acid (reacted with base)

NARCIENE

carboxylic group (__) - isolated from opium - carboxylic acid: stronger acid (form salts when reacted with bases0

HEAT

alkaloids are decomposed by _

STRYCHNINE AND CAFFEINE

alkaloids are decomposed by heat, except:

SUBLIME

instead of being decomposed by heat, strychnine and caffeine

HIGHER THAN 70 DEGREES CELSIUS

temperature in which alkaloids are decomposed

SUBLIMATION

conversion from solid to gas without passing through liquid phase (phase where strychnine and caffeine undergo instead of decomposition)

SOLUTION

decomposition occurs rapidly and easily when an alkaloid is in ___ than its dry form

N-OXIDES

most tertiary amine alkaloids are easily transformed to __

IODINE IN POTESSIUM IODIDE SOLN

reagent in Wagner's test

REDDISH BROWN PRECIPITATE

positive result for Wagner's test and Dragendorff's test

MERCURIC POTASSIUM IODIDE

reagent in Mayer's test

CREAMY PRECIPITATE

positive result for Mayer's Test

POTASSIUM BISMUTH IODIDE

reagent in Dragendorff's test

TRUE ALKALOIDS

derived from amino acids and have nitrogen in a heterocylic ring

TYPICAL ALKALOIDS

true alkaloids are also called

PROTO ALKALOIDS

derived from amino acids BUT DO NOT HAVE A NITROGEN in a heterocyclic ring

PSEUDO ALKALOIDS

NOT DERIVED from amino acids but have a nitrogen in a heterocyclic ring (non amino acid precursors - difference from true alkaloids)

FALSE ALKALOIDS

Non alkaloids that give a false positive reaction with alkaloidal reagents (not derived from amino acids & do not have nitrogen in heterocyclic ring)

-INE

trivial names should end by (alkaloids nomenclature)

1 - 2.5%

number of alkaloids present in Ephedra

80% EPHEDRINE AND PSEUDOEPHEDRINE

constituents isolated from Ma Huang

EPHEDRINE

isolated from EPHEDRA SINICA that increases metabolism while suppressing appetite (weight loss agent)

COLCHICINE

isolated from Meadow saffron / Autumn crocus used for gout (management - relief only) - prevent gout attack - prevent deposition of uric acid

3-DIMETHYXANTHINES

main purine alkaloid: caffeine - upon metabolism = ___

3,7-DIMETHYLXANTHINE

IUPAC name of theobromine

THEOBROMA OIL

used as a suppository base and as chocolates

THEOBROMINE

• isolated from cocoa
• works as vasodilator and bronchodilator, diuretic, stimulate smooth muscle (last 2 effects = used as lesser extend that theophylline)

CAFFEINE

main alkaloid found in tea

1,3-DIMETHYLXANTHINE

IUPAC name of theophylline

1,3,7-DIMETHYLXANTHINE

IUPAC name of caffeine

KOLACATECHIN

when nut of cola is dried = ___ (divided to caffeine and theobromine - characteristic brown color)

COCAINE (coca leaves) & CAFFEINE (kola nut)

2 main ingredients of Cola nitida

LOBELINE

• isolated from Wild tobacco
• antidepressant, emetic, respiratory stimulant, aid to smoking cessation, treatment of methamphetamine abuse

LOBELANIDINE, LOBELANINE

• constituents from Wild tobacco
• less potent and less studied; also known as emetic agent

PIPERINE

the alkaloid responsible for the pungency of black pepper

GONORRHEA

transmitting disease by bacteria that is treated by Piper nigrum

TROPANE ALKALOIDS

fusion of pyrrolidine and piperidine ring with common methylated nitrogen (Solanaceae and Erythroxylaceae)

TROPANE RING

tropane alkaloids contain _

NICOTINE

• major alkaloids found in tobacco (95%)
• constituent makes smoking addictive
• good use for the plant itself: natural insecticides (leaves - not want to eat tobacco - herbivored)

NORNICOTINE

demethylated form of nicotine (lack N-methyl group which is found in nicotine) - less potent

ANATABINE

• constituent from tobacco
• anti-inflammatory; currently studied for Alzheimer's disease

NORNICOTINE & ANATABINE

most abundant minor alkaloids found in Nicotiana tabacum

ANABASINE

insecticide isolated from Tobacco

RIPE FRUIT AND GREEN LEAVES OF BELLADONNA

highest concentration of atropine and scopolamine

ATROPINE

• isolated from Belladonna
• used for relaxing muscle spasms; can also be used for regulating heart rate (bradycardia - less than 60 bpm - slow HR)
• dilating the pupils (eye exam / eye surgery)
• poisoning by chloroform and opium

SCOPOLAMINE

• isolated from Atropa belladonna
• hyoscine
• used for nausea and vomiting associated with motion sickness
• nausea and vomiting post - operative

FETID NIGHTSHADE / STINKY NIGHTSHADE

synoynyms for Henbane

COCAINE

• isolated from Erythroxylum coca
• potent stimulant because it inhibits the reuptake of neurotransmitters norepinephrine, dopamine, serotonin
• increase alertness, euphoria, high energy

CINNAMOYL COCAINE

• constituent of Coca
• contains cinnamic acid ester instead of benzoyl group

TROPOCAINE

local anesthetic isolated from Coca

QUININE

first antimalarial; used for night muscle spasms isolated from Cinchona officinalis

QUINIDINE

anti-arrhythmic isolated from Jesuit's bark

CONCHININE AND CINCHONIDINE

antimalarial also isolated from Peruvian bark

OPIUM

• (1804) - morphine was isolated: gold standard - cause addiction (injection)
• codeine was isolated from - used for moderate pain; cough suppressant (oral)

PAPAVERINE

isolated from Opium that relaxes smooth muscle (muscle spasms)

NARCOTINE

cough suppressant isolated from Papaver somniferum

STEROIDAL ALKALOIDS

• arise by inclusion of a basic nitrogen at some point in the steroid molecule
• could act as a precursor for synthesis of various other steroids

WITHANINE

isolated from Ashwagandha (main constituent: 38%)

CONESSINE

constituent from Holarhenna antidysenterica; antimalarial

RESERPINE

• from Rauwolfia serpentina
• antihypertensive; antipsychotic agent (same as ajmalicine)

VINCRISTINE, VINBLASTINE

anti-cancer constituent from Catharanthus roseus

STRYCHNINE

• isolated from Crow fig
• heart, respiratory, body stimulant (toxic)

BRUCINE

• isolated from poison fruit
• traditional chinese medicine 9analgesic, anti-inflammatory, vomiting)

ERGONOVINE

constituent of ergot; oxytoxic, enhances labor, reduces bleeding

ERGOTAMINE

constituent of ergot; for migraine

LYSERGIC ACID

constituent of ergot; psychosomatic (pain associated with brain) -- addiction

LYSERGIC ACID DIETHYLAMIDE (LSD, LYSERGIDE)

addiction associated with one of the constituent of ergot of rye