ALKALOIDS Flashcards
(158 cards)
1
Q
these are basic organic heterocyclic nitrogenous compound usually physiologically active
A
traditional definition of alkaloids
2
Q
alkaloids are a ____ group
A
heterogenous
3
Q
FREE alkaloids are soluble in ____ and ____
A
ether, chloroform
4
Q
DEVIATION FROM DEFINITION
BASICITY:
some alkaloids are NOT basic, such as (3)
A
colchicine
piperine
quaternary alkaloids
5
Q
DEVIATION FROM DEFINITION
NITROGEN:
the nitrogen in some alkaloids is NOT in a heterocyclic ring such as (3)
A
ephedrine
colchicine
mescaline
6
Q
DEVIATION FROM DEFINITION
ORIGIN:
some alkaloids are derived from (5)
A
bacteria
fungi
insects
frogs
animals
7
Q
Alkaloids are cyclic organic compounds containing nitrogen in a negative state of oxidation with limited distribution among living organisms
A
modern definition of alkaloids
8
Q
one characteristic of alkaloids is that MOST alkaloids are ____ and SOME are ____
A
most are physiologically active, some are poisonous
9
Q
PURE alkaloids unite with acid to form ____
A
substituted ammonium salts
10
Q
____ alkaloids unite with acid to form substituted ammonium salts
A
PURE ALKALOISD
11
Q
Alkaloids are FREED from their salt by addition of ____
A
alkali
12
Q
alkaloids contains the element ____, and may exist as primary, secondary, tertiary, and quaternary
A
nitrogen
13
Q
alkaloids usually possess a ____ taste
A
bitter
14
Q
most alkaloids are ____ solids
A
crystalline
few are amorphous
15
Q
alkaloids are at liquid state for those that LACKS ____
A
oxygen
16
Q
alkaloids are soluble in ____
A
organic solvent
17
Q
alkaloids are insoluble in ____
A
water
18
Q
the majority of alkaloids are
(color)
A
colorless
19
Q
alkaloids decomposes with heat EXCEPT ____
A
caffeine
20
Q
alkaloids form doulbe bond salts with compounds of ____, ____, ____, and other heavy metals
A
mercury
gold
platinum
21
Q
REAGENTS that form double salts
(4)
A
Mayer’s
Dragendorff’s
Gold Chloride
Marme’s
22
Q
MAYER’s reagent
A
Mercuric Potassium Iodide
23
Q
DRAGENDORFF’s reagent
A
Potassium Bismuth Iodide
24
Q
MARME’s reagent
A
Potassium Cadmium Iodide
25
REAGENTS containing **halogens**
| (1)
Wagner's
26
**WAGNER's** reagent
Iodine in Potassium Iodide
27
REAGENTS **organic acids**
| (2)
Hager's
Tannic acid
28
**HAGER's** reagent
picric acid
29
REAGENTS that has **oxygenated high molecular weight acids**
| (3)
Sonnenschein's
Scheibler's
Silicotungestic acid
30
**SONNENSCHEIN's** reagent
Phosphomolybdic acid
31
**SCHEIBLER's** reagent
Phosphotungestic acid
32
**FROEHD's** reagent
phosphomolybdic acid
33
**MARQUI's** reagent
fromaldehyde / conc. H2SO4
34
**MANDALIN's** reagent
sulphovanidic acid
35
**ERDMANN's** reagent
conc. HNO3 / conc. H2SO4
36
**MECKE's** reagent
selenious acid / conc. H2SO4
37
**SHAER's** reagent
hydrogen peroxide / conc. H2SO4
38
**ROSENTHALER's** reagent
potassium arsenate / conc. H2SO4
39
# **REAGENT**
an **organic acid** reagent that can **precipitate alkaloid**
tannic acid
40
LIMITATIONS of alkaloids
limited distribution in nature
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* used as a **standard** in terms of **bitterness**
* it is the **most bitter tasting drug**
quinine
42
usually used **alkali** for **freeing** the alkaloids from their salt
ammonium hydroxide
43
# **CLASSIFICATION OF ALKALOIDS**
these alkaloids are **DERIVED** from **amino acids** and **HAVE** a **nitrogen IN a heterocyclic ring**
| e.g. Atropine
TRUE (Typical) ALKALOIDS
44
# **CLASSIFICATION OF ALKALOIDS**
these alkaloids are **DERIVED** from **amino acids** and **DO NOT HAVE nitrogen in a heterocyclic ring**
| e.g. Ephedrine
PROTOALKALOIDS
45
# **CLASSIFICATION OF ALKALOIDS**
these alkaloids are **NOT DERIVED** from **amino acids** but **HAVE nitrogen IN a heterocyclic ring**
| e.g. Caffeine
PSEUDOALKALOIDS
46
# **CLASSIFICATION OF ALKALOIDS**
these are **NON ALKALOIDS** that give **FALSE POSITIVE REACTION** with alkaloidal reagents
FALSE ALKALOIDS
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# **OCCURENCE / DSITRIBUTION**
alkaloids are ____ in **lower plants**
rare
48
# **OCCURENCE / DSITRIBUTION**
alkaloids are **more common** in ____
dicots
49
# **OCCURENCE / DSITRIBUTION**
FAMILIES **rich** in alkaloids
| (4)
Rubiaceae
Apocynaceae
Solanaceae
Papaveraceae
50
# **OCCURENCE / DSITRIBUTION**
FAMILIES **free** from alkaloids
Rosaceae
Labiatae
51
# **OCCURENCE / DSITRIBUTION**
what part of **DATURA** has alkaloids?
ALL parts
52
# **OCCURENCE / DSITRIBUTION**
part of **CINCHONA** that has alkaloids
barks
53
# **OCCURENCE / DSITRIBUTION**
part of **NUX VOMICA** that has alkaloids
seedds
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# **OCCURENCE / DSITRIBUTION**
part of **ACONITE** that has alkaloids
roots
55
# **OCCURENCE / DSITRIBUTION**
part of **BLACK PEPPER** that has alkaloids
fruits
56
# **OCCURENCE / DSITRIBUTION**
part of **TOBACCO** that has alkaloids
LEAVES
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# **OCCURENCE / DSITRIBUTION**
part of **OPIUM** that has alkaloids
LATEX
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Alkaloids are considered as ____ metabolites
secondary
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# **FUNCTION IN PLANTS**
alkaloids may act as ____ against **insects** and **herbivores**
protectant
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# **FUNCTION IN PLANTS**
alkaloids are, in certain cases, the **final products** of ____
detoxification
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# **FUNCTION IN PLANTS**
alkaloids are **source** of what **element**
nitrogen
62
# **FUNCTION IN PLANTS**
alkaloids act as **growth** ____ in certain **metabolic systems**
regulators
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# **FUNCTION IN PLANTS**
alkaloids can be utilized as a **source** of **energy** in case of **deficiency** in ____ assimilation
carbon dioxide
64
# **EFFECTS OF ALKALOIDS IN HUMANS**
alkaloids have ____ **biological activity**
high
65
# **EFFECTS OF ALKALOIDS IN HUMANS**
alkaloids produce varying degrees of **physiological** and **psychological responses** -- largely **interfering** with ____
neurotransmitters
66
# **EFFECTS OF ALKALOIDS IN HUMANS**
others **interfere** with ____, ____, and other processes
membrane transport, protein synthesis
67
# **EFFECTS OF ALKALOIDS IN HUMANS**
therapeutic value in **SMALL doses**
muscle relaxant
tranquilizers
pain killers
mind altering drugs
chemotherapy
68
# **EFFECTS OF ALKALOIDS IN HUMANS**
in **LARGE doses**, they are ____
highly toxic -- fatal
69
alkaloids affect the ____ - often by **influencing neurotransmitters**
central nervous system
70
CATEGORIES of **Psychoactive Alkaloids**
stimulants
hallucinogens
depressants
71
# **PSYCHOACTIVE ALKALOIDS**
alkaloids may also be ____
narcotic (addictive)
72
# **CATEGORIES OF PSYCHOACTIVE ALKALOIDS**
STIMULANTS
Cocaine
Ephedrine
Caffeine
| CAC
73
# **CATEGORIES OF PSYCHOACTIVE ALKALOIDS**
HALLUCINOGENS
Mescaline
Tropane
Ergot
Psilocybin
| MTEP
74
# **CATEGORIES OF PSYCHOACTIVE ALKALOIDS**
DEPRESSANTS
Morphine
Heroin
Codeine
| MHC
75
# **ALKALOID SYNTHESIS**
when alkaloids has an **aromatic acid precursor**, in what **pathway** was it synthesized?
shikimic acid pathway
76
# **ALKALOID SYNTHESIS**
PRECUROSOR of **nicotine**
nicotinic acid
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# **ALKALOID SYNTHESIS**
PRECURSOR of **caffeine**
Purine (xanthines)
78
# **ALKALOID SYNTHESIS**
some alkaloids are synthesized from **terpenes** through what **pathway**
Mevalonic acid pathway
79
# **ALKALOID SYNTHESIS**
these alkaloids are generlaly classified by the **predominant ring structure** and/or **carbon skeleton**
terpene-derived alkaloids
80
# **ALKALOID SYNTHESIS**
alkaloids classes with **ORNITHINE** as PRECURSOR
| (3)
Pyrrolidine
Tropane
Pyrrolizidine
81
# **ALKALOID SYNTHESIS**
alkaloid classes with **LYSINE** as PRECURSOR
Piperidine
Quinolizidine
82
# **ALKALOID SYNTHESIS**
ALTERNATIVE PRECURSOR of **piperidine**
acetate
83
# **ALKALOID SYNTHESIS**
alkaloid class with **TYROSINE** as PRECURSOR
Isoquinoline
84
# **ALKALOID SYNTHESIS**
alkaloid class with **TRYPTOPHAN** as precursor
Indole, Quinoline
85
# **NOMENCLATURE**
**ATROPINE** was named based on its ____
plant genus -- atropa
86
# **NOMENCLATURE**
**COCAINE** was named based on its ____
species -- coca
87
# **NOMENCLATURE**
**ERGOTAMINE** was named based on its ____
common name - ergot
88
# **NOMENCLATURE**
**PELLETIERINE** was named based on its ____
discoverer- pelletier
89
# **NOMENCLATURE**
**EMETINE** was named based on its ____
physiological action -- emetic
90
# **NOMENCLATURE**
**HYGRINE** was named based on its ____
prominent physical character -- hygroscopic
91
# **NOMENCLATURE**
an alkaloid that is named from the **Greek God of Dreams**
Morphine -- Morpheus
92
# **NOMENCLATURE**
PREFIX used that designates **N-demethylation** or **N-demethoxylation**
NOR-
(Norpseudoephedrine & Nornicotine)
93
# **NOMENCLATURE**
PREFIX used that designates **dehydration**
APO-
(Apomorphine)
94
# **NOMENCLATURE**
PREFIXES used to indicate **different types of isomers**
| (4)
Iso-
Pseudo-
Neo-
Epi-
95
# **NOMENCLATURE**
SUFFX that designates **isomerism**
-dine
(quinidine & cinchonidine)
96
# **NOMENCLATURE**
SUFFIX that indicates, in case of **ergot** alkaloids, a **LOWER pharmacological activity**
-ine
(ergotaminine is less potent than ergotamine)
97
# **CHEMICAL PROPERTY**
arrange the **basicity** of alkaloids based on their **type of amine** present
secondary > primary > tertiary
98
# **CHEMICAL PROPERTY**
TYPE OF AMINE present in **Norephedrine**
primary
99
# **CHEMICAL PROPERTY**
TYPE OF AMINE present in **Ephedrine**
secondary
100
# **CHEMICAL PROPERTY**
TYPE OF AMINE present in **Atropine**
tertiary
101
# **CHEMICAL PROPERTY**
TYPE OF AMINE present in **D-tubocurarine**
quaternary ammonium salts
102
# **BASICITY**
based on basicity, **CAFFEINE** is classified as ____
weak base
103
# **BASICITY**
based on basicity, **ATROPINE** is classified as ____
strong base
104
# **BASICITY**
based on basicity, **MORPHINE**, or any **phenolic alkaloids**, is classified as ____
amphoteric
105
# **BASICITY**
based on basicity, **NARCEINE**, or any alkaloids with **carboxylic groups**, is classified as ____
amphoteric
106
# **BASICITY**
based on basicity, **COLCHICINE** is classified as ____
neutral
107
# **EXTRACTION, PURIFICATION, & ISOLATION**
the powder is treated with **alkalis** to liberate the free bases that can then be **extracted** with **water immiscible organic solvents**
| **alkalinization** first then **extraction**
METHOD I
108
# **EXTRACTION, PURIFICATION, & ISOLATION**
the powdered material is **extracted** with **water** or **aqueous alcohol containing dilute acid**. alkaloids are extracted as their **salts** together with accompanying **soluble impurities**
METHOD II
109
# **EXTRACTION, PURIFICATION, & ISOLATION**
the powder is **extracted** with **water soluble organic solvents** such as **methanol** and **ethanol** which are **good solvents** for both **salts** and **free bases**
METHOD III
110
# **EXTRACTION, PURIFICATION, & ISOLATION**
METHOD I:
**solvents** used
water IMMISCIBLE organic solvents
| ether, petroleum spirit
111
# **EXTRACTION, PURIFICATION, & ISOLATION**
METHOD II:
**sovlents** used
water
or
aqueous alcohol containing dilute acid
112
# **EXTRACTION, PURIFICATION, & ISOLATION**
METHOD II:
alkaloids are **extracted** as their ____ together with accompanying ____
as their **salts** together with accompanying **soluble impurities**
113
# **EXTRACTION, PURIFICATION, & ISOLATION**
METHOD III:
**solvents** used
methanol
ethanol
114
# **EXTRACTION, PURIFICATION, & ISOLATION**
**good solvents** for both salts and free bases
water SOLUBLE organic solvents:
methanol
ethanol
115
METHODS OF OBTAINING ALKALOIDS
Maceration
Percolation
Continuous extraction (Soxhlet)
116
# **EXTRACTION, PURIFICATION, & ISOLATION**
the **best way** of extraction of **volatile** alkaloids
steam distillation
117
# **EXTRACTION, PURIFICATION, & ISOLATION**
the produced **steam** in steam distillation contain alkaloids received in ____ solution
acidic
118
**pigment** alkaloids
betalain alkaloids
119
these alkaloids are **restricted** to **club mosses**
Lycopodium alkaloids
120
class of alkaloids also referred to as **Pyrrolizidine alkaloids**
Pyridine alkaloids
121
**product** made from ***Nicotiana tabacum***
nicorette
122
**addictive smokable form** of COCAINE
Crack
123
consist of alkaloids and alkaloid salts obtained from the **bark** of certain **Cinchona species**
quinoline alkaloids
124
the amount of alkaloids (quinoline) present in **cinchona** depend on the ____
| (4)
species
environment of the tree
age
method of collection
125
a **reaction** used to identify **Quinine** (*Cinchona succirubra*)
thalleioquin reaction
126
REAGENTS used in **Thalleioquin reaction**
Br2, NH3 TS
127
**quinine** yields ____ color in **thalleioquin reaction**
emerald green
128
OPIUM alkaloids
| (6)
Morphine
Codeine
Ethylmorphine
Thebaine
Heroin
Papaverine
129
IPECAC alkaloids
| (4)
Emetine
Cephaeline
Psychottrine
Methylpsychotrine
130
IPECAC with OPIUM, used as **diaphoretic**
DOVERS POWDER
131
IPECAC with OPIUM
**Dovers Powder** is used as
diaphoretic
132
**least** amount of drug capable or producing **muscle relaxation** so the **head** of the animal **drop** in a characteristic manner
HEAD DROP DOSE
133
**OPIATE** analgesic
morphine
134
**Narcotic opiate** analgesic, antitussive
Codeine
135
OPIATE **smooth muscle relaxant**
heroine
papaverine
136
**Morphine** is SOLUBLE in ____ due to **phenols**
sodium hydroxide
137
**morphine** is SOLUBLE to **sodium hydroxide** due to ____
phenols
138
**Codeine** is PRECIPITATED by ____
sodium hydroxide
139
class of alkaloids found in **Ergot** & **Nux vomica**
indole alkaloids
140
an **indole** alkaloid used as **CNS stimulant**, **lethal** in **large doses** (used as a poison)
strychnine
141
**Ergot** alkaloids are based on ____
lysergic acid
(LSD - lysergic acid diethylamide)
142
TWO important alkaloids of **Nux vomica**
strychnine
brucine
143
***Rauwolfia serpentina*** (Indian snakeroot) contains **indole** alkaloids useful for the treatment of ____
hypertension
144
***Gelsemium sempervirens*** contains
gelsemine
sempervine
145
use of **BRUCINE**
alcohol denaturant
146
**alkaloid-like** amines
PROTOALKALOIDS
147
**Ephedrine** and **Adrenaline** are both examples of ____
PROTOALKALOIDS
148
effects of **Ephedrine** and **Adrenaline**
broncho**dilation**
increased heart rate
peripheral vasoconstriction
149
also known as **NON-alkaloids**
Purine alkaloids
150
**synthetic** origin of **purine alkaloids** does **NOT** contain an intact ____
amino acid
151
**PURINE alkaloids** have **peculiar solubility** in ____ and in ____
warm water & chlorinated solvents
152
# **BASICITY**
what is the basicity of **PURINE alkaloids**
amphoteric
153
a **PURPLE** color is derived from **caffeine** and other **purine derivatives** druing WHAT TEST
MUREXIDE test
154
____ does **NOT precipitate** like most alkaloids
Caffeine
155
a purine alkaloid that **relaxes involuntary muscles** **more effectively** than caffeine or theobromine
theophylline
156
this purine alkaloid **stimulates** the **CNS** and has a **weak diuretic action**
caffeine
157
a purine alkaloid that has **OPPOSITE action** with CAFFEINE
theobromine
158
**OPIUM** is also called as ____
stone of immortality
