M2 (Pharmacognosy) Alkaloids

nitrogenous

Organic __ compounds with varied pharmacologic

actions

basic pH, bitter taste; usually crystalline or amorphous

pH, taste, nature of alkaloids

Coniine, Nicotine, Sparteine, Arecoline (CANS)

only liquid alkaloids

white

they are generally __ solid substance

berberine, sanguinarine

__ (yellow) and __

(colorless, yields red salts).

mescaline, ephedrine, atropine, tubocurarine

> Primary amine: RNH2, __

> Secondary amine: R2NH, __

> Tertiary amine: R3N, __

> Quaternary amine: __

strychnine, lsd

alkaloids derived from L-tryptophan

morphine, papaverine

alkaloids derived from L-tyrosine

piperidine; coniine, lobeline

[STRUCTURE AND ALKALOID PRODUCT DERIVED] lysine

pyridine, pyrrolidine; nicotine

[STRUCTURE AND ALKALOID PRODUCT DERIVED] ornithine-aspartate

tropane; cocaine, atropine, hyoscyamine, scopolamine

[STRUCTURE AND ALKALOID PRODUCT DERIVED] ornithine

quinoline; quinine

[STRUCTURE AND ALKALOID PRODUCT DERIVED] tryptophane

isoquinoline; morphine

[STRUCTURE AND ALKALOID PRODUCT DERIVED] tyrosine

purine; caffeine

[STRUCTURE AND ALKALOID PRODUCT DERIVED] purine (aspartate, glycine, glutamine)

free alkaloids

alkaloidal base

insoluble, soluble

alkaloidal bases are __ in water, __ in organic solvents

salt form

form of alkaloids soluble in water

inorganic base

alkaloidal salts to alkaloidal base

inorganic acid

alkaloidal base to alkaloidal salts

derosne

discovered narcotine

serturner

discovered morphine

pelletier and caventou

discovered brucine, emetine, strychnine, piperine, quinine, caffeine, colchicine, coniine

schiff

discovered coniine

fungi

organisms with lysergic acid derivatives and sulfur-containing alkaloids

amphibians

true alkaloids are also present in

ephedra, taxus

pteridophytes

true alkaloids

almost all compounds considered to be alkaloids have their

nitrogen atoms enclosed within a ring system, and are called __

pseudoalkaloids

heterocyclic "alkaloids" that are not derived from amino acids are called __

protoalkaloids

alkaloids with no nitrogenous alkaloids are called __

physiological action

protoalkaloids are alkaloids due to their __ rather than their chemical nature

coniine, arecoline

pyridine and piperidine examples

hyoscyamine, atropine

tropane examples

quinine, cinchonine

quinolone examples

morphine, codeine

isoquinoline examples

ergotamine, physostigmine

indole examples

pilocarpine

imidazole examples

caffeine, theobromine

purine examples

hygrine, stachydrine

pyrrole and pyrrolidine examples

arogenic acid

prephenate (transamination) --> __ --> phenylalanine, pyrosine

anthranilic acid

chorismate --> __ --> serine, tryptophan

phenyl hydroxylase

the presence of __ is tested in babies (newborn

screening) since tyrosine is the precursor of dopamine, norepinephrine, melanin, etc.

phenylketonuria

if phenyl hydroxylase is lacking, there would be mental retardation, CNS/brainis affected, etc., called __

quaternary amine + carbanion; mannich-type condensation

synthesis of alkaloids

pyridine-piperidine

P alkaloids

ornithine or aspartate, lysine, ornithine or aspartate, ornithine

[P ALKALOIDS]

> Pyridine - from __

> Piperidine - from __

> Pyrrolidine - from __

> Pyrrolizidine - from __

Nicotiana tabaccum, nicotine, pyrrolidone, smoking deterrent, CNS stimulant, cholinergic neurotransmitter

[P ALKALOIDS] nicotine

> scientific name:

> constituent:

> derivative of __

> use:

areca catechu, arecoline, masticatory (betel chewing), taenicide, anthelmintic, mouth/esophageal cancer

[P ALKALOIDS] areca nut / betel nut / nga nga

> sci name

> constituent

> use: __ (betel chewing), __, __ (veterinary)

> high tannin content provides a risk for: __

lobelia inflata, lobeline, smoking deterrent, resuscitation of newborn infants, paralytic

[P ALKALOIDS] LOBELIA / INDIAN TOBACCO

> scientific name

> constituent: __ (less addictive than nicotine)

> use: __ (ingredient in tablets and lozenges), __

> in toxic doses: __

conium maculatum, apiaceae, coniine, mouse like odor, draught, death, Socrates

[P ALKALOIDS] POISON HEMLOCK

> scientific name

> family

> constituent

> with KOH, it develops strong, __, due to the liberation of coniine

> used by greeks for preparing __, which criminals were put to __

> scientist killed with this thru lethal injection

duboisia myoporoides, atropine, hyscyamine, scopolamine

[P ALKALOIDS] DUBOISIA

> scientific name

> chief source of __

> other constituents present: __, __

duboisia hopwoodii, nicotine, nornicotine, tobacco

[P ALKALOIDS] PITURI/AUSTRALIAN TOBACCO

> scientific name

> constituents

> used like __

pyrrolizidine alkaloids

hepatotoxic alkaloids

carcinogenic, mutagenic

other risks of pyrrolizidine alkaloids

comfrey, coltsfoot

[PYRROLIZIDINE ALKALOIDS] ecologic role in some species of butterflies

comfrey

[PYRROLIZIDINE ALKALOIDS] was used to treat HTN w/o extensive studies, causing people to have hepatic necrosis and problems

antitumor

[PYRROLIZIDINE ALKALOIDS] indicine - use

glycosidase inhibitory activity

[PYRROLIZIDINE ALKALOIDS] australine - use

alkylating pyrrole esters

[PYRROLIZIDINE ALKALOIDS] hepatotoxic properties are believed to arise by

breakdown to __

bicyclo [3.2.1]

tropane is a __ structure

ornithine, putrescine, and acetate

[TROPANES] suggested precursor

methionine

[TROPANES] N-methyl group

phenylalanine

[TROPANES] tropic acid

atropa belladonna, hyoscyamine, atropine, racemic mixture, hyoscyamine, anticholinergic, antimuscarinic, organophosphate poisoning, pupil dilation (mydriasis)

[TROPANES] BELLADONNA / DEADLY NIGHTSHADE

> scientific name

> constituent

> atropine is a __ mixture of __

> uses: __ (mydriatic, antidiarrheal, spasmolytic/antispasmodic); __ (sympa effect)

> antidote to __

> sap of belladonna is used for __ to look beautiful

datura stramonium, hyoscyamine, scopolamine, anticholinergic, asthma

[TROPANES] STRAMONIUM / JIMSON WEED / JAMESTOWN WEED

> sci name

> constituent

> use: __, vapor from burnt weed relieves __

hyosyamus niger, hyoscyamine, scopolamine, anticholinergic

[TROPANES] HYOSCYAMUS / HENBANE

> sci name

> constituent

> use

hyoscyamus muticus, hyoscyamine

[TROPANES] EGYPTIAN HENBANE

> sci name

> constituent

datura metel, datura fastuosa, scopolamine, hyocscine, twilight sleep, antimuscarinic, motion sickness, pre-anesthetic sedative depressant, CNS depressant, calming delirium, anticholinergic

[TROPANES] TALUMPUNAY / THORNAPPLE

> sci name

> constituent: rich source of __

> another name for scopolamine

> scopolamine + morphine = __

> uses: __, __ (transscop or transderm scop), __

> feature that makes this not ideal/addicting: __, __, __

- wtihania somnifera

- tropine, pseudotropine, hygrine

- sedative

[TROPANES] WITHANIA / ASHWAGANDA

> sci name

> constituents

> use

- mandragora officinarum

- madragorine, hyoscyamine, scopolamine

- stimulant

[TROPANES] MANDRAGORA / EUROPEAN MANDRAKE

> sci name

> constituents

> use of mandragorine

tropic acid

[TROPANES] aromatic portion of hyoscyamine and scopolamine

scopoline

[TROPANES] tropane portion of scopolamine

tropine

[TROPANES] tropane portion of atropine and hyoscyamine

epoxide

[TROPANES] different structure in scopolamine

asthma., motion sickness, control secretions pre-op, eye examinations, physiologic antidote

[TROPANES] uses of belladonna alkaloids

amino alcohol esters

[TROPANES] belladonna alkaloids are __

- erythroxylum coca, e. truxillense

- divine plant of the incas

- cocaine

- local anesthetics, vasoconstrictor

- psychomotor, euphoric, abuse

- dopamine

- brompton's cocktail, severe pain in terminal cancer

- morphine

- coca chewing

[TROPANES] COCA

> sci name

> also called as the: "__"

> prototype of __, innate __ effect

> use: __ stimulant, __, with strong __ potential

> blocks reuptake of __

> ingredient in __ (cocaine + morphine), to control __

> cocaine potentiates analgesic effect of __

> __ is part of native culture in colombia, peru, argentina

b-carboline

[QUINOLINE ALKALOIDS] results of mannich reactions: involving a-carbon of the indole nucleus from tryptophan affords a __ derivative

indolenine

[QUINOLINE ALKALOIDS] results of mannich reactions: reaction with b-position gives __

psychomimetic

[QUINOLINE ALKALOIDS] results of mannich reactions: properties of b-carbolines

extensive liver damage

[QUINOLINE ALKALOIDS] results of mannich reactions: ADR of quinolizidines

- cinchona succirubra

- cinchona calisaya

- quinine, quinidine

- antimalarial, antiarrythmic

- cinchonism; loss of hearing, ringing in ears, impaired sight

- emerald green

[QUINOLINE ALKALOIDS] CINCHONA/PERUVIAN BARK

> sci name (red cinchona)

> sci name (yellow cincohona)

> constituents

> use of constituents

> overdose and its effects

> result under thalleoquine reaction

- cuprea bark, dita

- quinidine

- ditamine, antimalarial

[QUINOLINE ALKALOIDS] CINCHONA/PERUVIAN BARK

> related drugs: __ (remijia pedunculata), __ (alstonia scholaris)

> cuprea bark is the commercial source for __

> dita/australian quinine bark contains __, its use is __

- heme to hemozoin

- cardiac arrythmias, Afib

[QUINOLINE ALKALOIDS] CINCHONA/PERUVIAN BARK

> quinine prevents conversion of __

> quinidine as prophylaxis for __, and tx of __

- campototheca acuminata

- nyssaceae

- camptothecin (CPT)

- topoisomerase inhibitors

- irinotecan, topotecan

- tx of several types of cancer (colon, lung)

[QUINOLINE ALKALOIDS] HAPPY TREE

> sci name

> fam name

> constituents

> act as __ especially in malignant cells

> captothecin derivatives

> use of camptothecin derivatives

benzylisoquinoline

consists most of the said isoquinolines

tetrahydroisoquinoline

special class of isoquinolines

dopamine, tyrosine

isoquinoline alkaloids are derived from __, which originated from __

ipecac

[ISOQUINOLINE ALKALOIDS] forms methylenedioxy group

thebaine, heroin

[ISOQUINOLINE ALKALOIDS] dimethylmorphine

- cephalis ipecacuanha

- cephaeline, emetine, psychotrine

- local emetic, poison antidote kits

- dover's powder, diaphoretic

- emetine HCl

- protein synthesis

[ISOQUINOLINE ALKALOIDS] IPECAC

> sci name

> constituents

> use: __ (irritant in GI), __

> 10% opium + ipecac; its use

> antiprotozoan, antiamebic preparation given IM and SC

> MOA of emetine is to block __

10% opium + ipecac

dover's powder content

- hydrastis canadensis

- hydrastine, berberine, canadine

- astringent

[ISOQUINOLINE ALKALOIDS] GOLDENSEAL / HYDRASTIS

> sci name

> constituent

> use: __ in inflammation of mucous membranes

- sanguinaria canadensis

- papaveraceae

- sanguinarine, chelerythrine, protopine

- red salts

- stain faces, emetic, stimulant

[ISOQUINOLINE ALKALOIDS] BLOOD ROOT / SANGUINARIA

> sci name

> family name

> constituents

> sanguinarine forms __ salts

> use

- strychnos castelnaei

- longaniaceae

- tubocurarine

- nondepolarizing skeletal muscle relaxant

- block nerve impulses

- head drop test in rabbits

[ISOQUINOLINE ALKALOIDS] SOUTH AMERICAN ARROWHEAD POISON / TUBOCURARINE / CURARE

> sci name

> family

> constituent

> use: __ without deep anesthesia

> MOA: __ to skeletal muscles --> paralyzing effect

> least amount of drug capable of producing relaxation experiment

- papver somniferum

- stone of immortality

- morphine

- serturner

- CNS stimulant then depressant, narcotic analgesic, hypnotic

[ISOQUINOLINE ALKALOIDS] OPIUM

> sci name

> also known as: "__"

> constituent

> who first isolated morphine?

> use

morphine, codeine, noscapine, papverine, thebaine

[ISOQUINOLINE ALKALOIDS] content of indian opium

Prepared Opium BP/EP

[ISOQUINOLINE ALKALOIDS] contains 10% morphine and minimum 1% codeine; thebaine limited to 3.0%

paregoric/camphorated opium tincture, laudanum/opium tincture/deodorized opium tincture, poppy seed/maw seed

[ISOQUINOLINE ALKALOIDS] related drugs to opium: __, __, __

antiperistaltic, antiperistaltic, used in baking

[ISOQUINOLINE ALKALOIDS]

use of

> paregoric/camphorated opium tincture,

> laudanum/opium tincture/deodorized opium tincture,

> poppy seed/maw seed

morphine

[ISOQUINOLINE ALKALOIDS] [opium alkaloids] most important opium alkaloid