[PCOG] Alkaloids

alkaloids

organic nitrogenous compounds; bitter, crystalline or amorphous

coniine, arecoline, nicotine, sparteine

the only liquid alkaloids

alkaloidal base

alkaloids that are insoluble in water, soluble in organic solvents

alkaloidal salts

alkaloids that are freely soluble in water

Potassium mercuric iodide

Mayer's reagent

Iodine in potassium iodide

Wagner's reagent

Mercuric iodide

Valser's reagent

Potassium bismuth iodide

Dragendroff's reagent

Cadmium in potassium iodide

Marme's reagent

Phosphomolybdic acid

Sonnenchein's reagent

Phosphotungstic acid

Scheibler's reagent

Marquis

specific alkaloidal test for codeine (Marquis rgt = blue)

Hasemann

specific alkaloidal test for codeine (Ferric chloride rgt = blood red)

Vitali

specific alkaloidal test for atropine (Nitric acid rgt = gray ppt)

Guilielmo

specific alkaloidal test for atropine (sulfuric acid rgt = red w/ flower odor)

Gerard's

specific alkaloidal test for atropine (ethanol, mercuric chloride rgt = yellow)

Thalleioquin

specific alkaloidal test for quinine (Acetic acid, chlorine water,ammonia = fine blue fluorescence, then green ppt with ammonia)

Mandelin

specific alkaloidal test for strychnine (Mandelin rgt = violet)

Murexide

specific alkaloidal test for caffeine (Potassium chlorate and HCl = purple; pink on paper chrom)

non-heterocyclic alkaloids

lacks one or more properties of alkaloids in that they are feeble bases; contain nitrogen in a side chain; alkaloids due to their physiological action rather than their chemical nature

true alkaloids

nitrogenous heterocycle; derived from amino acid

pseudoalkaloids

nitrogenous heterocycle; not derived from amino acid

protoalkaloids

not a nitrogenous heterocyle; derived from amino acid

pyridine & piperidine

coniine, arecoline

tropane

hyoscyamine, atropine

quinoline

quinine, cinchonine

isoquinoline

morphine, codeine

indole

ergotamine, physostigmine

imidazole

pilocarpine

purine

caffeine, theobromine

pyrrole & pyrrolidine

hygrine, stachydrine

Nicotiana tabaccum

nicotine

nicotine

derivative of pyrrolidine; smoking deterrent, CNS stimulant, cholinergic neurotransmitter

Areca catechu

areca nut/betel nut/nganga

areca nut

stimulant masticatory (betel chewing), taenicide, anthelminthic (veterinary)

areca nut

has high tannin content -> risk of mouth/esophageal cancer

Lobelia inflata

lobella/Indian tobacco

lobeline

less addictive than nicotine

lobelia/Indian tobacco

smoking deterrent (ingredient in tablets and lozenges)

Atropa belladona

belladone/Deadly nightshade

racemize

hyoscyamine -> ________ -> atropine

belladona

antidote for organoPO4 and strychnine poisoning; anticholinergic (mydriatic, antidiarrheal, spasmolytic)

Hyoscyamus niger

hyoscyamus/Henbane; anticholinergic (hyoscyamine)

Hyoscyamus muticus

Egyptian Henbane

Datura stramonium

stramonium/Jimson weed/Jamestown weed;

Jimson weed

vapor from burnt weed relieves asthma, anticholinergic (hyoscyamine, scopolamine)

Datura metel/fastuosa

talumpunay/thornapple

talumpunay/thornapple

rich source of scopolamine (antimuscarinic, for motion sickness, pre-anesthetic sedative, depressant)

Withania somnifera

withania

withania

sedative (tropine, pseudotropine, hygrine)

Duboisia myoporoides

duboisia; chief source if atropine; also has hyoscyamine, scopolamine

Duboisia hopwoodii

pituri/Australian tobacco; has nicotine, nornicotine; used like tobacco

Mandragora officinarum

mandragora/European mandrake (hyoscyamine, scopolamine, mandragorine)

Erythroxylon coca or Huanuco coca

coca/coca leaves

coca

divine plant of the Incas

cocaine

prototype of local anesthetics; innate vasoconstrictor effect; counteracts morphine-induced sedation and respiratory depression

coca/coca leaves

psychomotor stimulant, euphoric, with strong abuse potential; MOA: blocks reuptake of Dopamine; ingredient in Brompton's Cocktail

Brompton's cocktail

used to control severe pain in Cancer

morphine

cocaine potentiates analgesic effect of ______

Cinchona succirubra

red cinchona/cinchona/peruvian bark

Cinchona calisaya

yellow cinchona/Calisaya bark

loss of hearing, ringing in the ears, impaired sight

cinchonism or cinchona overdose

quinidine

antiarrythmic cinchona alkaloid

quinine

antimalarial cinchona alkaloid

Thalleioquine reaction

reaction that identifies quinine and quinidine (emerald green)

Remijia purdieana

cuprea bark; commercial source of quinidine

Alstonia scholaris

dita/Australian quinine bark; antimalarial (ditamine)

Cephaelis ipecacuanha

Rio/Brazillian ipecac

ipecac

local emetic (irritant to GI); in poison antidote kits (emetine, cephaline, psychotrine)

Dover's powder

10% Opium + Ipecac (diaphoretic)

Emetine HCl

MOA: block protein synthesis; antiprotozoan, antiamebic (IM, SC)

Hydrastis canadensis

hydrastis/goldenseal; astringent in inflammation of mucus membranes (hydrastine, berberine, canadine)

Sanguinaria canadensis

sanguinaria/blood root

sanguinaria/blood root

used by Indians to stain their faces

Strychnos castelnaei

tubocurarine/curare/South American arrow poison

tubucurarine/curare

Skeletal muscle relaxant without deep anesthesia; MOA: block nerve impulses to skeletal muscles -> paralyzing effect

head drop test in rabbits

least amount of drug capable of producing rel

Papaver somniferum

opium/gum opium; CNS stimulant then depressant, narcotic analgesic, hypnotic

opium

stone of immortality

Serturner

isolated morphine from opium

Indian opium

only licit source of opium

paregoric

Camphorated Opium Tincture (antiperistaltic)

laudanum

Deodorized Opium Tincture (antiperistaltic)

poppy seed

maw seed (baking)

morphine

most important opium alkaloid (narcotic analgesic, hypnotic)

N&V, constipation

AE of morphine

codeine/methylmorphine

most widely used opium alkaloid (antitussive, sedative, narcotic analgesic)

heroin/diacetylmorphine

habit-forming; more pronounced effects than morphine

apomorphine

central emetic for poisonings; dehydrated morphine

papaverine

smooth muscle relaxant, antitussive

hydromorphone

powerful narcotic analgesic, strong respiratory depressant

hydrocodone

antitussive

noscapine/narcotine

antitussive, no narcotic properties ("anarcotine")

diphenoxylate & loperamide

antidiarrheal opium alkaloid

meperidine & fentanyl

anesthetic opium alkaloid

Rauvolfia serpentina

rauwolfia/Indian snakeroot

reserpine

inhibit entry of dopamine to vesicle -> no NE

rauwolfia

hypotensive, sedative, tranquilizer, psychotherapeutic effect

Catharantus roseus

catharantus/vinca/periwinkle/chichiricA

catharantus/vinca

antineoplastic, oncolytic; MOA: arrest cell division at metaphase, anti-mitotic