Lesson 7.3. Tropane Alkaloids

bicyclo[3.2.1.]

Tropane is a _____________ structure

Ornithine, Putrescine, and Acetate

____________________________ are suggested precursors of Tropanes.

N-methyl group

The _______________________ of tropanes are from methionine

Tropic acid

The _______________________ of tropanes are derived from phenylalanines.

Atropa belladonna

TROPANE ALKALOIDS:

The Deadly Nightshade

Scientific Name: ?

Family:

Constituents:

Solanaceae

TROPANE ALKALOIDS:

The Deadly Nightshade

Scientific Name:

Family: ?

Constituents:

Hyoscyamine (Atropine)

TROPANE ALKALOIDS:

The Deadly Nightshade

Scientific Name:

Family:

Constituents: ?

Jamestown Weed/Thronapple/Angel’s Trumpet

TROPANE ALKALOIDS:

Jimsonweed

Synonym: ?

Scientific Name:

Family:

Constituents:

Datura stramonium

TROPANE ALKALOIDS:

Jimsonweed

Synonym:

Scientific Name: ?

Family:

Constituents:

Solanaceae

TROPANE ALKALOIDS:

Jimsonweed

Synonym:

Scientific Name:

Family: ?

Constituents:

Hyoscyamine (0.25%)

TROPANE ALKALOIDS:

Jimsonweed

Synonym:

Scientific Name:

Family:

Constituents: ?

Datura innoxia, Datura metel, and Datura fastuosa

TROPANE ALKALOIDS:

Jimsonweed

• other scientific names

scopolamine

TROPANE ALKALOIDS:

Jimsonweed

• Datura fastuosa is the chief source of _______________

Stinking nightshade

TROPANE ALKALOIDS:

Henbane

Synonym: ?

Scientific Name:

Family:

Constituents:

Hyoscyamus niger

TROPANE ALKALOIDS:

Henbane

Synonym:

Scientific Name: ?

Family:

Constituents:

Solanaceae

TROPANE ALKALOIDS:

Henbane

Synonym:

Scientific Name:

Family: ?

Constituents:

Hyoscyamine (0.05%)

TROPANE ALKALOIDS:

Henbane

Synonym:

Scientific Name:

Family:

Constituents: ?

B-annus

TROPANE ALKALOIDS:

Henbane

1. annual variation

2. biennial variation

1 = ?

a-biennis

TROPANE ALKALOIDS:

Henbane

1. annual variation

2. biennial variation

2 = ?

burn

TROPANE ALKALOIDS:

Henbane Uses:

• for preparations intended to a._______ for relief of b.______________

a = ?

asthma

TROPANE ALKALOIDS:

Henbane Uses:

• for preparations intended to a._______ for relief of b.______________

b = ?

belladonna and stramonium

TROPANE ALKALOIDS:

Henbane

• resembles a.__________________________ in action but b.________

a = ?

weaker

TROPANE ALKALOIDS:

Henbane

• resembles a.__________________________ in action but b.________

b = ?

Hyoscyamus muticus

TROPANE ALKALOIDS:

Henbane

• scientific name of Egyptian henbane

Duboisia myoporoides

TROPANE ALKALOIDS

Duboisia

Scientific Name: ?

Family:

Constituents:

Solanaceae

TROPANE ALKALOIDS

Duboisia

Scientific Name:

Family: ?

Constituents:

Hyoscine and Hyoscyamine

TROPANE ALKALOIDS

Duboisia

Scientific Name:

Family:

Constituents: ?

atropine

TROPANE ALKALOIDS

Duboisia

• It is a good source of a.______________

• Principally b.______________ and related alkaloids

a = ?

nicotine

TROPANE ALKALOIDS

Duboisia

• It is a good source of a.______________

• Principally b.______________ and related alkaloids

b = ?

Duboisia hopwoodii

TROPANE ALKALOIDS

Duboisia

• scientific name of Pituri

Withania somnifera

TROPANE ALKALOIDS

Aswagandha

Scientific Name: ?

Family:

Constituents:

Solanaceae

TROPANE ALKALOIDS

Aswagandha

Scientific Name:

Family: ?

Constituents:

Tropine and Hygrine

TROPANE ALKALOIDS

Aswagandha

Scientific Name:

Family:

Constituents: ?

Tropine and Hygrine

TROPANE ALKALOIDS

Aswagandha

Scientific Name:

Family:

Constituents: ?

Sedative

TROPANE ALKALOIDS

Aswagandha

• use

amino alcohol esters

TROPANE ALKALOIDS

• Belladonna alkaloids are _____________________________

tropic acid

TROPANE ALKALOIDS

Belladonna Alkaloids

• The aromatic portion in all of them is a._________________

• Scopolamine’s tropane portion is called b.________________, for atropine is c.______________. The difference is an d.______________ in scopolamine

a = ?

scopoline

TROPANE ALKALOIDS

Belladonna Alkaloids

• The aromatic portion in all of them is a._________________

• Scopolamine’s tropane portion is called b.________________, for atropine is c.______________. The difference is an d.______________ in scopolamine

b = ?

tropine

TROPANE ALKALOIDS

Belladonna Alkaloids

• The aromatic portion in all of them is a._________________

• Scopolamine’s tropane portion is called b.________________, for atropine is c.______________. The difference is an d.______________ in scopolamine

c = ?

epoxide

TROPANE ALKALOIDS

Belladonna Alkaloids

• The aromatic portion in all of them is a._________________

• Scopolamine’s tropane portion is called b.________________, for atropine is c.______________. The difference is an d.______________ in scopolamine

d = ?

anticholinergic

TROPANE ALKALOIDS:

USES OF BELLADONNA ALKALOIDS:

• their uses root from their ___________________ property.

Asthma

TROPANE ALKALOIDS:

USES OF BELLADONNA ALKALOIDS:

• associated with henbane

• quaternary atropine derivatives (Ipratropium and Tiotropium)

Motion Sickness

TROPANE ALKALOIDS:

USES OF BELLADONNA ALKALOIDS:

• associated with scopolamine (Hyoscine N-butylbromide)

Control of secretions pre-op

TROPANE ALKALOIDS:

USES OF BELLADONNA ALKALOIDS:

• associated with Hyoscine HBr

Mydriatic for Eye Examinations

TROPANE ALKALOIDS:

USES OF BELLADONNA ALKALOIDS:

• associated with Atropine

organophosphate poisoning

TROPANE ALKALOIDS:

USES OF BELLADONNA ALKALOIDS:

• antidote for ___________________________________

Erythroxylum coca

TROPANE ALKALOIDS:

Coca

Scientific Name: ?

Family:

Constituents:

Erythroxylaceae

TROPANE ALKALOIDS:

Coca

Scientific Name:

Family: ?

Constituents:

Cocaine, Ecgonine, Cuscohygrine

TROPANE ALKALOIDS:

Coca

Scientific Name:

Family:

Constituents: ?

cocaine synthesis

TROPANE ALKALOIDS:

Coca

• Ecgonine can be used as a precursor for _______________

Colombia, Peru, Argentina

TROPANE ALKALOIDS:

Coca

• Chewing is part of native culture in a._____________________

• It is abused by b._________________________, and leads to tolerance and dependence.

a = ?

inhalation (free basing) or IV

TROPANE ALKALOIDS:

Coca

• Chewing is part of native culture in a._____________________

• It is abused by b._________________________, and leads to tolerance and dependence.

b = ?

local anesthetic

TROPANE ALKALOIDS:

Coca Uses:

1. used as ____________________ but toxic and addictive

2. used in _______________________ along with Morphine which is an analgesic in terminal cancer

1 = ?

Brompton’s Cocktail

TROPANE ALKALOIDS:

Coca Uses:

1. used as ____________________ but toxic and addictive

2. used in _______________________ along with Morphine which is an analgesic in terminal cancer

2 = ?