Medicinal Chemistry-I, Unit 3B. cholinergic blocking agent.pptx

Cholinergic Blocking Agent
Mr. Mote Ganesh Dnyandev
Assistant Professor, Annasaheb Dange College of B.Pharmacy, Ashta
Mr. Mote G.D, ADCBP, Ashta

Classification of Antimuscarinic(Parasympatholytics)
Parasympatholytics
Solanaceous alkaloids and
analogues
Atropine sulphate, Hyoscyamine sulphate,
Scopolamine hydrobromide, Homatropine
hydrobromide, Ipratropium bromide*
Synthetic cholinergic blocking
agents
Tropicamide, Cyclopentolate hydrochloride, Clidinium
bromide, Dicyclomine hydrochloride*, Glycopyrrolate,
Methantheline bromide, Propantheline bromide,
Benztropine mesylate, Orphenadrine citrate, Biperidine
hydrochloride, Procyclidine hydrochloride*,
Tridihexethyl chloride, Isopropamide iodide,
Ethopropazine hydrochloride.

Structure s of Solanaceous alkaloids
O H
C
O
O
S c o p o l a m i n e
O
N
C H 3
9 - m e t h y l - 3 - o x a - 9 - a z a t r i c y c l o [ 3 . 3 . 1 . 0 2 , 4 ] n o n a n - 7 - y l ] ( 2 S ) - 3 - h y d r o x y - 2 - p h e n y l p r o p a n o a t e
N C
H
3
O
C
H
C
O
C
H
2 O
H
C
H
H
3
C H
2
C B
r
I
p
r
a
t
r
o
p
i
u
m
B
r
o
m
i
d
e
[
8
-
m
e
t
h
y
l
-
8
-
(
1
-
m
e
t
h
y
l
e
t
h
y
l
)
-8
-
a
z
o
n
i
a
b
i
c
y
c
l
o
[
3
.
2
.
1
]o
c
t
-
3
-
y
l
]3
-
h
y
d
r
o
x
y
-
2
-
p
h
e
n
y
l
-
p
r
o
p
a
n
o
a
t
e
N C H 3
O
C H
C
O
H o m o A tro p in e
O H
8 -m eth y l-8 -aza-b icy clo [3 .2 .1 ]o ctan -3 -y l 2 -h y d ro x y -2 -p h en y lacetate
N C H 3
O
C
C
O
A t r o p i n e
N C H 3
O
C
O
H 2 C
H
H O
H 2 C
H O
H
H y o c y a m i n e
8 - m e t h y l - 8 - a z a -
b i c y c l o [ 3 . 2 . 1 ] o c t a n - 3 - y l 3 -
h y d r o x y - 2 - p h e n y l p r o p a n o a t e
8 - m e t h y l - 8 - a z a - b i c y c l o [ 3 . 2 . 1 ] o c t a n -
3 - y l 3 - h y d r o x y - 2 - p h e n y l p r o p a n o a t e
S - i s o m e r
R - i s o m e r

Structure s of Synthetic Analogues
H2C
OH
C
O
N
H2C
CH3
N
N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
Tropicamide(Mydriatics)
N CH3
O
C
C
O
Clidinium bromide
(Anticholinergic-reduces acid secretion
reduces bowel spasm)
OH
Br-
C
O
O
H2C
H2C
N
H3C
H3C
Dicyclomine(Antispasmodic)
HO
O
O
N
CH3
CH3
H
Glycopyrrolate(peptic ulcer treatment)
{[cyclopentyl(hydroxy)phenylacetyl]oxy}-1,1-dimethylpyrrolidin-1-ium O
O
O
N
H3C
CH3
CH3
Br-
2-(9H-xanthene-9-carbonyloxy)-N,N-diethyl-N-methylethanaminium bromide
Methanthelinebromide
(Treatment of peptic ulcer)
C H
C
H O
O
O
N
C H 3
C H 3
( C y c l o p e n t o la t e ( M y d r ia ti c s a n d C y c lo p le g i c )
2 - ( d im e th y la m i n o ) e th y l 2 - ( 1 - h y d r o x y c y c lo p e n ty l ) - 2 - p h e n y l a c e t a t e

O
O
O
N
H3C
CH3
CH3
Br-
Propanetheline Bromide
(to treat urinary incontinence, hyperhidrosis,
as well as cramps and spasms of the stomach,
intestines, and bladder)
H3C
CH3
N-(2-(9H-xanthene-9-carbonyloxy)ethyl)-N-isopropyl-N-methylpropan-2-aminium bromide
N CH3
O
CH
S O
O
CH3
OH
3-(benzhydryloxy)-8-methyl-8-aza-bicyclo[3.2.1]octane
Benztropine(Antiparkinsonism,Muscle control)
CH
O
H2
C
H2
C
N
H3C
H3C
2-(benzhydryloxy)-N,N-dimethylethanamine
CH2COOH
C COOH
HO
CH2COOH
orphenadrine citrate
to help relax certain muscles in your body and
relieve the stiffness, pain, and discomfort caused by
strains, sprains, or other injury to your muscles
OH
N
biperiden hydrochloride( treatment of parkinsonism)
1-(bicyclo[2.2.1]hept-5-en-2-yl)-1-phenyl-3-(piperidin-1-yl)propan-1-ol

C
H2
C C
H2
N
HO
Procyclodine(Antiparkinsonism)
1-cyclohexyl-1-phenyl-3-(pyrrolidin-1-yl)propan-1-ol
HO
N Cl-
3-cyclohexyl-N,N,N-triethyl-3-hydroxy-3-phenylpropan-1-aminium
chloride
tridihexethyl chloride(to treat acquired
nystagmus or peptic ulcer disease)
C
CH2
O
H2N
CH2 N
CH3
H3C
H3C CH3
CH3
4-amino-N,N-diisopropyl-N-methyl-4-oxo-3,3-
diphenylbutan-1-aminium
isopropamide(treatment of peptic ulcer and
other gastrointestinal disorders marked by
hyperacidity and hypermotility
S
N
N
CH3
H-Cl
N,N-diethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
ethopropazine hydrochloride( Parkinson's disease
or movement disorders (extrapyramidal signs-
EPS) due to the side effects of certain psychiatric
drugs (antipsychotics such as
chlorpromazine/haloperidol)

Synthesis of Ipratropium Bromide
N CH3
HO
+
CH
C
O
OH
CH2 OH
Tropic acid
N CH
3
O
CH
C
O
CH2 OH
Atropine
Br
H
C CH3
CH3
N CH3
O
CH
C
O
CH2 OH
CH
H3C H2C Br
Ipratropium Bromide

Synthesis of Dicyclomine
CN
H2C CH2 CH2
H2
C
Br
H2O
H2
C CH2
Br
HOOC
HO CH2
H2
C
N
CH3
CH3
2-(dimethylamino)ethanol
Cyclohexyl Nitrile
1,6 dibromo xane
1-cyclohexylcyclohexanecarboxylic acid
C
O
O
H2C
H2C
N
H3C
H3C
Dicyclomine(Antispasmodic)

Synthesis of Procyclodine
C CH3
O
acetophenone
+ H C
O
H + HN
pyrrolidine
formaldehyde
C
O
H2
C C
H2
N
Mannich Cond
CH3COOH
1-phenyl-3-(pyrrolidin-1-yl)propan-1-one
BrMg
+
C
H2
C C
H2
N
HO
Addition
hydrolysis
Procyclodine(Antiparkinsonism)

Medicinal Chemistry-I, Unit 3B. cholinergic blocking agent.pptx

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Medicinal Chemistry-I, Unit 3B. cholinergic blocking agent.pptx