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Wilson and gisvolds

Textbook of organic medicinal and pharmaceutical chemistry

Sedatives and Hypnotics and Antianxiety


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Sedatives and Hypnotics and Antianxiety

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Introduction
In general, sedative-hypnotics are drugs used to slow down mental and physical functions of the body.
These are also referred to as the CNS depressants.

Sedatives are chemical agents tend to produce a calming effect, relax muscles, and relieve feelings of
tension, anxiety, and irritability.

At higher doses, most of these sedative drugs will also produce drowsiness and eventually produce sleep.
Drugs that have such a sleep-inducing effect are called Hypnotic drugs or Hypnotics.

Hypnotic-sedative are used in treatment of some of Insomnias (unsatisfactory or insufficient sleep)


There is, no sharp distinction between sedative and hypnotic and the same drug may have both actions
depending on the method of use and the dose employed.
The combination of the terms sedative-hypnotic appropriately identifies the major pharmacological effects of
these drugs.
In reality, almost any drug that calms, soothes, and reduces anxiety is also capable of relieving insomnia.
Antianxiety drugs are used to treat excessive or inappropriate anxiety, such as post-traumatic stress,
generalised anxiety, panic attack, social phobia, and obsessive-compulsive disorders.

Unlike the narcotics, intoxicating doses of the sedative-hypnotics usually result in impaired judgement,
slurred speech, and loss of motor function.

Mechanism of action is by positive modulation of action of GABA at GABAA receptor.


They are primarily used for daytime sedation and the treatment of seizure disorders or mild anxiety.

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Classification:
According to chemical structures, sedative-hypnotics and antianxiety drugs are broadly classified as:

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Barbiturates
Barbiturates are central nervous system (CNS) depressants (medicines that cause drowsiness).
Barbiturates produce a wide spectrum of CNS depression, from mild sedation to coma, and have been
used as sedatives, hypnotics, anaesthetics, and anticonvulsants.
However, they can be addictive and abused.
Excessive doses can cause depression, slurred speech, slowed reflexes, and confusion.
Barbiturates were first introduced for medical use in the early 1900s.
More than 2,500 barbiturates have been synthesized, and in the height of their popularity about 50 were
marketed for human use.

Barbiturate Development
In 1864, von Baeyer synthesized the first barbiturate, barbituric acid.
Barbiturates are usually taken orally but are sometimes injected intravenously or intramuscularly (I.M.).
They are absorbed rapidly; 30-40% is bound to plasma protein, and the rest is distributed to muscle, fat,
and the liver (where they are ultimately inactivated).

Classification of Barbiturates
Barbiturates are classified in 4 types based on their duration of action;
1) Ultra-short acting
2) Short acting
3) Intermediate acting
4) Long acting
1) Ultra short acting barbiturates: The ultra-short acting barbiturates produce anesthesia within about one
minute after intravenous administration.
Those in current medical use are Methohexital, Thiamylal and thiopental.
2) Short acting barbiturates: Action starts within 1/2 hour and lasts for about 4 hours.
Ex: Pentobarbitone, Quinalbarbitone, Secobarbitone, Cyclobarbitone
3)

Intermediate acting barbiturates: Action starts within 1/2 hour and lasts for about 6 hours.
Ex: Allobarbitone, Butobarbitone, Amylobarbitone

4) Long acting barbiturates: Action starts within 1/2 hour and lasts for 8 hours.
Ex: Barbitone, Phenobarbitone, and Methyl-Phenobarbitone.

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Chemistry of Barbiturates
Barbiturates are derivatives of barbituric acid (2,4,6-trioxyhexahydropyrimidine) which is devoid of hypnotic
and sedative activities.

Structure-Activity Relationships (SAR) of Barbiturates;

1) Hypnotic activity: Side chains at position 5 (especially if one of them is branched) is essential for activity.
2) Potency and duration of action: Length of side chain at position 5 influences potency and duration of
action.
Ex: Secobarbital and Thiamylal are slightly more potent than pentobarbital and thiopental, respectively.
3) More rapid onset and shorter duration of action: Sulphur instead of oxygen atom at position 2 has more
rapid onset of action but shorter duration.
Ex: Thiamylal and Thiopental have more rapid onset and shorter duration of action than secobarbital and
pentobarbital, respectively.
4) Increased incidence of excitatory side effects: Methylation at position 1 (Methohexital) enhances
excitatory side effects.
5) Increased potency, rate of onset and short action: Generally, an increase in the lipophilicity of the
compound results in more rapid onset of action accompanied with an increase in potency.
Introduction of polar groups (hydroxyl, keto, amino, or carboxyl) into C-5-alkyl side chain makes the
compound more hydrophilic in nature. Due to the polar nature, hydrophilic barbiturates do not dissolve in
microsomal membranes of liver and are excreted.
Branched, cyclic or unsaturated side chain at C-5 position generally reduce the duration of action due to an
increased ease of metabolic conversion to a more polar, inactive metabolite.
6) Stereoisomerism: Though their L-isomers are nearly twice as potent as their D-isomers, barbiturates are
marketed as racemic mixtures. Methohexital has two asymmetric carbon atoms, so exists as 4
stereoisomers (, -D, L-Methohexital).
Different activities among different stereoisomers (enantiomers or enantiomorphism) is consistent with site
of action at a chiral center of a receptor or enzyme.

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Mechanism of Action of Barbiturates


Most likely site of action of barbiturates is Gamma-Amino-Butyric Acid (GABA) receptor complex.
GABA is the principal inhibitory neurotransmitter in the mammalian CNS.
GABA receptor complex is made of 4 to 6 glycoprotein subunits assembled to form a ligand-gated chloride
ion channel
Barbiturates enhance and mimic the action of GABA at the GABA receptor complex.
Barbiturate binding to this receptor decreases the rate of GABA dissociation and increases the duration of
GABA-activated chloride channel opening. At slightly higher concentrations, barbiturates directly activate
chloride channel opening even in the absence of GABA, leading to barbiturate anesthesia.

Side-effects of Barbiturates
Side effects of barbiturates include hangover with drowsiness, dizziness, ataxia, respiratory depression,
hypersensitivity reactions, headache, particularly in elderly; paradoxical excitement and confusion
occasionally precede sleep.

Acidity:
Various type of barbiturates show acidic properties which is due to lactom-lactim and keto-Enol
tautomerism. All four hydrogens are involved.

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The salt formation readily takes place in Dioxi form

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Long acting
Barbiturates
1) Barbital

2) Phenobarbital

3) Mephobarbital

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Barbital S

Trade name: Barbitone, Veronal

Synthesis:

Uses:
1) Discontinued as sedative-Hypnotic but is interesting molecule, because of biological consequences of
its low lipid/water partition coefficient.
2) It is slowly eliminated mostly intact by the kidney.
Duration of action: 4-12 hr.
Onset of action: 0.5-1 hr.

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Phenobarbital S

Trade name: Luminal


Synthesis:

Properties
1) White glistering small crystals
2) pKa 7.1
3) Insoluble in water and soluble in alcohol
4) 65% of drug as metabolized largely to inactive p-hydroxy phenyl derivatives
Uses:
1) Long acting sedative-Hypnotic
2) Used as Anti-convulsant especially in generalized tonic-clonic and partial seizures.
3) Useful in nervous and related tension state.
30-120= Sedative

50-100= Anti-convulsant

100-320=Hypnotic

Duration of action: 4-12 hr.


Onset of action: 0.5-1 hr.
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Mephobarbital

Methylphenobarbitone

Trade name: Prominal

Properties:
1) Mephobarbital is white crystalline,
2) Water insoluble powder
3) It is soluble in aqueous solutions of alkali hydroxides and carbonates

Uses:
1) Principle use is Anti-convulsant
2) It is metabolically N-Dealkylated to Phenobarbitone which is considered responsible for almost all
activity, long acting barbiturate.
Duration of action: 1-4 hr.
Onset of action: 0.25 hr.

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Intermediate acting
Barbiturates
1) Amobarbital

2) Butabarbital

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Amobarbital S

Amobarbitone
Trade name: Amytal

Synthesis:

Properties:
1) It occurs as white crystalline powder.
2) It is slightly soluble in water but freely soluble in alkali hydroxide and carbonate solutions.

Uses:
1) An intermediate acting barbiturate
2) Used as Anti-convulsant
3) Used in surgery (pre-operative)

Duration of action: 2-8 hr.


Onset of action: 0.25-0.5 hr.

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Butabarbital S

Butobarbitone
Trade name: Butisol

Synthesis:

Properties:
1) It is white crystalline powder

2) Slightly soluble in water


Uses:
1) An intermediate acting barbiturate
2) Used principally as Sedative-Hypnotic
Duration of action: 2-4 hr.
Onset of action: 0.5 hr.

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Short acting
Barbiturates
1) Pentobarbital

2) Secobarbital

3) Talbutal

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Pentobarbital

Pentobarbitone
Trade name: Nembutal

Properties:
1) Pentobarbitone is available as Pentobarbitone sodium salt.
2) Pentobarbitone and its sodium salt are available as white, crystalline powder.
3) Pentobarbitone is slightly soluble in water, whereas its sodium salt is freely soluble in water.

Uses:
1) As short acting barbiturate in producing sedation and as Anti-convulsant

Duration of action: 2-4 hr.


Onset of action: 0.5 hr.

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Talbutal

Trade name: Lotusate

Uses:
1) As short acting barbiturate
Duration of action: 2-4 hr.
Onset of action: 0.5 hr.

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Secobarbital S

Quinalbarbitone
Trade name: Seconal

Synthesis:

Properties:
1) Its sodium salt
2) Quinalbarbitone sodium is a white powder.
3) It is freely soluble in water.

Uses:
1) Its short acting barbiturate
2) It is widely used as sedative and hypnotic
3) It is used in epilepsy
4) Used as local anesthetic
5) In toxic reactions of strychnine
Duration of action: 1-4 hr.
Onset of action: 0.25 hr.
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MISCALLANEOUS

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Amides and imides:


A group of acyclic amides and imides, some bearing a close structural relationship to the barbiturates, have
proved to be effective as sedative-Hypnotic drugs.
Numerous heterocyclic derivatives with low toxicity for hypnotic and sedative properties were synthesized.

Glutethimide S

Synthesis:

Properties:
1) Glutethimide is Colorless or white color
2) Water insoluble powder
3) Soluble in alcohol
4) It should be stored in light protected containers.

Uses:
1) Glutethimide is used as hypnotic in all types of insomnia. It induces sleep without

2) Clinical use now limited due to addition and chronic use leads to toxic psychosis and convulsions
Duration of action: 4-8 hr
Onset of action: 30 min

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Methaqualone S

Synthesis:

Properties:
1) It is a Quinazolione derivative
2) Methaqualone is white crystalline,
3) Water insoluble powder
4) It should be stored in a light protected container.

Uses:
1) Methaqualone is used as a hypnotic and as daytime sedative
2) Administered along with anti-histamine agent like Diphenhydramine

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Methyprylon

Properties:
1) Methyprylon is a white crystalline powder having characteristic odor.
2) It is sparingly soluble in water but freely soluble in alcohol, chloroform, and ether.
3) It should be stored in well-closed containers.

Uses:
1) It is useful for induction of sleep within 15 to 30 minutes in patients with simple insomnia
2) Closely resemble secobarbital in its onset and duration of action.
3) Habituation, tolerance, physical dependence and addiction can occurs

Duration of action: intermediate

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Alcohols and their carbonated derivatives


Ethanol has a long history of use as sedative and hypnotic
Because of the many problems associated with the use of alcohol, such as the development of chronic
alcoholism on continued use, other depressant drugs have been favored for sedative-hypnotic use.
Widely used in self-medication as a sedative-hypnotic
Seldom preferred medically due to many hazards
Hypnotic activity of the normal alcohols increases as the molecular weight and the lipid-solubility
increases, reaching a maximum depressant effect at 8 carbons.
branching of alkyl chains increases depressant activity, and the order of potency in an isomeric series of
alcohols is

3 > 2 > 1

Replacement of a H2 atom by halogen has an effect equivalent to increasing the alkyl chain and for the
lower molecular weight alcohols, result in increased potency.
Most of alcohols and Carbamates have suppressed as sedative and hypnotics. Some dysfunctional
compounds (Diol Carbamates) have present action on the cord in addition to brain and are retained for
their skeletal muscular relaxant properties.

Ethchlorvynol

Properties:
1) Ethchlorvynol is a colourless to yellow color liquid with characteristic odor.
2) It is light sensitive drug hence should be protected from light.

Uses:
1) Is most useful in the induction of sleep for patients with simple insomnia
2) It is use as daytime sedative
Duration of action: 5hr.
Onset of action: fairly rapid hr.

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Meprobamate S

Synthesis:

Properties:
1) Meprobamate is an odourless, white color crystalline aggregate with bitter taste.
2) It is insoluble in water but soluble in alcohol and slightly soluble in ether.

Uses:
1) Meprobamate is used to induce sleep in anxiety and tensive patients.
2) It also possesses anticonvulsant and muscle relaxant properties.

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Aldehydes and their derivatives


Few aldehydes and their derivatives are valuable hypnotic drugs. Chloral hydrate acts as hypnotics.
It acts principally through it is metabolite trichloro ethanol. Paraldehyde is a cyclic trimmer derivative of
acetaldehyde.

Chloral hydrate S

Synthesis:

Properties:
1) Chloral hydrate is white crystalline powder, Colorless, slightly bitter taste, and characteristic odor
2) It is Very soluble in water and in alcohol

Uses:
1) Chloral hydrate is a sleep-inducing drug used in the early 1900s but seldom used today.
2) It is a short acting agent useful gastric patients
3) Chloral hydrate is used as hypnotic to treat insomnia and to allay anxiety as sedative.
4) The sleep is light, and the patient is readily aroused

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Paraldehyde S

Synthesis:

Properties:
1) Paraldehyde is available as Colorless or pale yellow color liquid.
2) It has strong characteristic odor and is soluble in water.
3) Paraldehyde should be stored in airtight, light protected containers
4) The drug is more potent and toxic than ethanol but less so than chloral hydrate
5) The chief objection to the use of paraldehyde is disagreeable taste, which is difficult to mask
.

Uses:
1) Used exclusively in the management of hospitalized patients undergoing alcohol withdrawal
2) CNS depressant activity resembles at of alcohol and chloral hydrate
Duration of action: 8 hr
Onset of action: 15 min

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Triclofos sodium

Properties:
1) Triclofos sodium is hygroscopic, white color,
2) Water soluble powder

Uses:
1) Used as hypnotic and sedative

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Benzodiazepine derivatives:
Azepine and its tautomers:
Azepine usually denotes 1H, which itself is very unstable and rapidly rearranges to its tautomer 3H
azepine, which is most stable of all Azepines. 2H and 4H are also theoretically possible.
Benzodiazepine derivatives have become increasingly important as antianxiety, anticonvulsant,
antipsychotic, and sedative-hypnotic drugs.
The initial synthesis of the 1,4-benzodiazepines
Diazepines are unsaturated seven membrane ring containing two nitrogen atoms (1,2;1,3;1,4 diazepines
or derivatives of them)

Benzodiazepine and benzodiazepine like drugs bind to a benzodiazepine recognition site, one of
allosteric sites that modulate the effect of GABA binding to GABAA receptor
The benzodiazepine recognition site is an in the extracellular N terminus of the 1,2,3,5 subunits
The field of Chlordiazepoxide by stem bach.
SAR of benzodiazepines for antianxiety acting has been studied, the general structure is:

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1) An electronegative substitution at position 7 is required for activity and more electronegative it is, the hyper
activity.
2) Position 6, 8, 9 should not be substituted
3) Phenyl at position 5 promotes activity.
If this phenyl group is ortho position (2) or Diortho (2, 6) substituted with electron attracting substituents,
activity is increased,
If this phenyl group is Para, substitution decreases activity greatly.
4) Saturation of 4-5 double bond or a shift of it to 3-4 position decreases activity.
5) Alkyl substitution at position 3 decreases activity, substitution with a OH group does not
6) Presence or absence of 3-hydroxyl group is important pharmacokinetically
7) The 2-carbonyl function is optimal for activity, as is the nitrogen atom at position 1
8) The N-substituent should be small; such drugs bind to plasma proteins, the more non-polar the better
binding and greater distribution to brain.
They have few interactions. Low drug abuse, greater margin of safety.

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Chlordiazepoxide S

Trade mane: Librium


Synthesis:

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Properties:
1) Is a colorless crystalline substance
2) Light soluble in water but insoluble in aqueous solution
3) Absorbed well from GIT and excreted slowly
4) Demoxepam is metabolite, which converts to Nordiazepam, which in turn converts to oxazepam,
and this undergoes conjugation to excrete the glucuronides.
5) It is belong to category of sedative
6) Half-life 6 30 hrs

Uses:
1) Used in the treatment of anxiety and tension

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Diazepam S

Trade name: Valium


Synthesis:

Properties:
1) It is white or Colorless crystalline,
2) Water insoluble powder
3) It should be stored in a well-closed container, protected from light.

Uses:
1) It is used for the control of anxiety and tension state, the relief of muscle spasm, and for the
management of acute agitation during withdrawal from alcohol
2) It has significant anticonvulsant properties
3) Diazepam is metabolized in the liver, one of the metabolites being the 3-hydroxy derivative,
oxazepam, which is also active as sedative and muscle relaxant.

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Oxazepam

Trade name: Serax

Properties:
1) It has a lower incidence of side-effect and reduced toxicity, perhaps due to the ease of conjugation
of the 3-OH group
2) It is one of metabolites of diazepam
3) More polar in nature
4) Duration of action is short

Uses:
1) As anti-anxiety agent

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Clorazepate dipotassium

Properties:
1) This is considered as a prodrug
2) It is inactive itself, undergo rapid loss of water and then decarboxylation to Nordiazepam which has
long life and undergo hepatic conversion to form oxazepam

Uses:
1) As an anti-anxiety agent
2) Its biological activity is due to its rapid invivo decarboxylation and formation of Nordiazepam

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Prazepam

Properties:
1) Prazepam occurs as Colorless, crystalline powder.
2) It is practically insoluble in water but soluble in alcohol and chloroform.
3) The major metabolite is Nordiazepam and hence has long half-life (half-life 63 hrs.)

Uses:
1) It is sedative and antianxiety drug
2) It is used for short-term relief from anxiety

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Lorazepam S

Synthesis:

Properties:
1) It is white powder

6) Lorazepam is related to oxazepam

2) Insoluble in water

7) Owing to its higher lipophilicity, Lorazepam

3) 2-chloro substituted increases activity

requires a lower dose than does oxazepam to

4) Mean half-life is 12 hrs.

produce its anti-anxiety effects

5) Metabolism is rapid because of 3-OH group

Uses:
1) It is used for insomnia due to anxiety
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Halazepam

Properties:
1) It is white crystalline powder
2) Active metabolite is Nordiazepam and oxazepam

Uses:
1) As anxiolytic; half-life is 14 hours

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Flurazepam hydrochloride

Properties:
1) Flurazepam is white or yellow crystalline powder and is odourless
2) Flurazepam occurs as hydrochloride salt
3) Freely soluble in Water and alcohol

Uses:
1) Flurazepam is a hypnotic or minor tranquilizer
2) Exclusively for insomnia
3) Metabolite is N-dealkyl flurazepam.
4) Long half-life, hence has long lasting effect may be up to 1 month.

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Alprazolam S

Synthesis:

Properties:
1) It is a Triazolo analogue of 1,4-benzodiazepine
2) It is short acting benzodiazepine as protein binding is low and oxidative metabolism of methyl group is
rapid

Used:
1) It is highly potent as anxiolytic an a milligram basis.

Mechanism of action
Alprazolam is a short acting benzodiazepine receptor agonist acting at various sites in the CNS.
It has been used for short-term relief of anxiety and mental depression.

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Sedative-Hypnotics and Anti-axiety


Drugs
Barbitura
tes

Non-barbiturates

Barbiatal

Amobar
bital

Pentobarb
ital

Phenoba
rbital

Butabarb
ital

Secobar
bital

Mephobar
bital

Benzodiazepines

Clordiazepoxide

Diazepam

Talobarbi
tal
Oxazepam

Potassium
chlorazepate
Parazepam
Amides
and
imides

Alcohols and
their
carbamate
derivatives

Glutethimide

Ethchloervyno
l

Methaquallon
e

Meprobamat
e

Methyprylon

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Aldehydes
and
their
derivatives

Lorazepam

Chloral
hydrate

Halazepam

Paraldehyde

Flurazepam

Triclofos
sodium

Alprazolam

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