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SUBJECT FORENSIC SCIENCE

Paper No. and Title PAPER No. 9: of Abuse

Module No. and Title MODULE No. 24: Date

Module Tag FSC_P9_M24

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Drugs

TABLE OF CONTENTS

1. Learning Outcomes

2. Introduction

3. Forensic Issues

4. Some Notable Date Rape Drugs

4.1

4.2 Gamma Hydroxy Butyrate (GHB)

4.3

4.4 Clonazepam

4.5 Methylenedioxymethamphetamine (MDMA)

4.6 Lysergic Acid Diethylamide

5. Pharmacodynamics

6. Identification of Date Rape Drugs

7. Summary

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

1. Learning Outcomes

After studying this module, you will be able to know about

 The Drugs used for Sexual Assaults  Mode of action and pharmacokinetics of some Date Rape Drugs  Forensic Examination of common Date Rape Drugs

2. Introduction

Sexual attacks are largely committed on women; while they are debilitated by so-called „Date- Rape Drugs‟ became the attention of many investigations conducted by law enforcement agencies in many countries. In the late 1990s a discernable increase in reports of this crime as well as in the number of scientific publications on the subject was witnessed. The list of drugs related with is extensive and among others consist of flunitrazepam with other such as clonazepam, , , oxazepam, Gamma- Hydroxybutyrate (GHB), ketamine and . In a characteristic situation, a potential sexual offender surreptitiously spikes the drink of an unsuspecting person with a sedative drug for the purpose of „drugging‟ and consequently sexually assaulting the victim while the victim is under the influence of this substance. Victims generally report loss of memory during and after these incidents. They wake up in unacquainted places, inappropriately dressed and often with the sense but not the actual remembrance of having had sex.

3. Forensic Issues

Included in a special class named “Date- Rape Drugs” does not exempt these drugs from their scientific examination forensically. On the contrary it increases their forensic importance as they may be frequently encountered by the investigating agencies in metropolitan cities. Recovery of unknown samples of whichever physical state is done by the IO from events like Parties are meticulously sent to the forensic laboratory for their chemical examination and identification so as to enable the prosecution to reprimand the illegal activity. In the present scenario, when the crime against women are increasing day by day, it is not less than a requirement for the administration to curb out such misuse or rather abuse of drugs which is unfortunately used for the commission of heinous crimes. The members of this class actually belong to various drug classes like benzodiazepines, , etc. Therefore, the forensic examination is required as same as for the other classes of drugs.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

4. Some Notable Date Rape Drugs

4.1 FLUNITRAZEPAM

The best-known drug related with sexual assault is Flunitrazepam also known as Rohypnol. Flunitrazepam [5-(2-fluorophenyl)-1, 3-dihydro-1-methyl- 7-nitro-2H-1, 4-benzodiazepin-2- one)] belongs to the 7-nitro group of benzodiazepines. Its effect overcomes over the sedative, anxiolytic and muscle-relaxing effects of other compounds from the same pharmacological group.

Flunitrazepam exists in the form tablets and in injectable form in about 80 countries around the world. It has a much stronger affinity for the Gammaaminobutyric Acid (GABA) receptor than Diazepam (Valium). In fact, it is 10 times as potent as diazepam. Rohypnol tablets are trafficked into the USA and sold with street names such as Roofies, Rophies, RoRohypnolopies, Rib, Rope, Pappas, Peanuts, Pastas, Forget pills, Ro-shays, Roaches and Roche. Roche have reformulated tablets so that they give a blue colour when dissolved in water, thereby alerting drinkers to the fact that their drinks have been spiked.

4.2 GAMMA HYDROXY BUTYRATE (GHB)

Other drugs that have been associated in sexual assault include gamma-hydroxybutyrate (GHB) and related compounds which are converted to GHB such as gamma-butyrolactone (GBL) and 1, 4-butanediol (1, 4-BD). GHB is sold on the streets under names such as Salty Water, Scoop, Soap, Liquid X, Natural Sleep-500 and Liquid Ecstasy.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

It is used in date rape because it is effective rapidly, is relatively easy to manufacture and obtain, and is alleged to have aphrodisiac properties. Possession, sale and clandestine manufacturing of GHB are illegal in many countries including the USA, UK and Japan.

GHB is rapidly metabolised and eliminated from the body. The detection window for blood is about 6 hours and for urine is about 8 hours. GHB is endogenously produced in the human body and in some foods and this need to be taken into account when carrying out an analysis for GHB.

4.3 KETAMINE Ketamine (Ketalar, Ketaject, Vetalar) is used in human and veterinary treatment for introduction of anaesthesia for short surgical techniques and routine veterinary examination. It was introduced to the market in the 1960s as a unique anaesthetic agent. When abused, ketamine can produce psychotic symptoms and cognitive impairment that may persist for up to 3 days. Clinically, ketamine has been used to induce schizophrenia as a model of psychosis. Like PCP, ketamine induces short-lived psychotic symptoms in non-schizophrenic volunteers.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

It is structurally related to (PCP), but has only 25% of the psychotomimetic activity of PCP. Recently, there has been a reappearance of interest in ketamine due to its advent as a „‟ at rave parties and at bars. On the streets it is known as „K‟, „Special K‟ and „Cat Valium‟ and by many other names. The chief source for ketamine is diversion from veterinary clinics where it is available as a parenteral solution. Ketamine is used in a liquid form, its pharmaceutical preparation, or as a powder formed by allowing the solvent of the injectable to evaporate. It is taken voluntarily by intramuscular injection or by the intranasal or oral routes. Ketamine can be ingested involuntarily when it is unknowingly added to a drink to induce a stupor for Drug Facilitated Sexual Assault, i.e. as a „date-rape‟ drug.

4.4 CLONAZEPAM Clonazepam (5-(2-chlorophenyl)-1, 3-dihydro-7- nitro-2H-1,4-benzodiazepin-2-one) is an anticonvulsant and it shows many of the effects common to all benzodiazepines. It is available in tablets containing 0.5mg, 1mg and 2mg under the trade names Klonopin, Clonex, Iktorivil and Rivotril.

It is a CNS that results in loss of voluntary muscle control and loss of inhibition, and reduces . Like some other benzodiazepines, it causes . The onset of action of clonazepam is between 30 and 60 minutes, and duration of action may last up to 12 hours.

4.5 METHYLENEDIOXYMETHAMPHETAMINE (MDMA) Methylenedioxymethamphetamine (MDMA) is the prototypical member of a large series of phenethylamine designer drugs and has become one of the main drugs of abuse in many countries in Northern Europe. Clandestine production is centered largely in Europe.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

A number of homologous compounds with broadly similar effects, such as methylenedioxyamphetamine (MDA), MDEA and N-methyl - 1- (1, 3- benzodioxol -5 -yl) -2 –butanamine (MBDB) have also appeared, but have proved less popular. These substances are collectively known as the „ecstasy‟ drugs.

Several methods of synthesis can be employed, including: • An amine displacement method using safrole as the starting material • A pathway via the intermediate 1-(3,4-methylenedioxyphenyl)- 2-propanone (MDP2P) with isosafrole or a nitrostyrene as the starting material Identifying reaction intermediates and by-products can help identify the synthetic route.

4.6 LYSERGIC ACID DIETHYLAMIDE Lysergic acid diethylamide (LSD) is a drug of group that causes hallucination. Abuser will imagine images hear sounds and experience sensations that look as if it is real but do not occur. Certain also create abrupt and random fluctuations in the temper of those who take them.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

LSD (lysergic acid diethylamide), first formed in 1938, is a very potent hallucinogen. It is prepared from lysergic acid, which is originated in ergot, a fungus that grows on rye and other grains. LSD is formed in crystalline form and then merged with excipients, or diluted as a liquid for forming in ingestible forms. It is odorless, colorless and has a considerably bitter taste. LSD is retailed in tablet form (generally small tablets called as Microdots), on Sugar Cubes, in thin squares of gelatin (usually denoted to as Window Panes), and most commonly, as blotter paper (sheets of absorbent paper soaking in or saturated with LSD, enclosed with colorful schemes or artwork, and perforated into one-quarter inch square, individual dosage units).

5. Pharmacodynamics

Since these drugs are used for a particular purpose; the main prerequisite is to be of soporific in nature in order to lessen the resistance of the victim. Therefore, drugs used for such purpose is not restricted in a certain or specific class but many drugs which are having sedative effect may be included safely in under the heading of Date- Rape Drugs. Subsequently, each drug has its own mechanism of action and fate inside the body. Some of them are detailed below: 5.1 Flunitrazepam Flunitrazepam is readily absorbed through the gastrointestinal tract and metabolised almost completely by the liver. Its metabolism includes reduction to 7-aminoflunitrazepam and then to the N-glucuronide, demethylation to the N-demethyl metabolite, hydrolysis to the 3-OH metabolite and then to the O-glucuronide. Approximately 90% of its metabolites are excreted through the urine and 10% in the faeces. Deaths involving flunitrazepam in conjunction with other central nervous system (CNS) , such as , but also due to overdose of flunitrazepam alone, have been reported. Flunitrazepam is often used to enhance the effects of , or marijuana.

5.2 Clonazepam Clonazepam is metabolised in the liver to 7-aminoclonazepam by reduction of the 7-nitro group (Fig. 10.5). This is followed by hydroxylation at the 3-carbon and subsequent glucuronidation. Almost the entire parent drug is metabolised and less than 0.5% of clonazepam is excreted unchanged in the urine. The elimination half-life from plasma has been reported as being between 19 and 60 hours. The apparent volume of distribution ranges between 1.5 and 6.2 L/kg. After a 2 mg dose of clonazepam, the peak concentration of both parent compound and 7-aminoclonazepam in blood occurs 2 hours after ingestion. Clonazepam is a highly potent benzodiazepine with a relatively low affinity for the benzodiazepine receptor. It must cross the blood–brain barrier to get to its site of action.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

The ability of a drug to cross this barrier depends on protein binding, lipid solubility and ionization constant. Clonazepam is largely non-ionised at physiological pH and relatively water insoluble, so it readily crosses biological membranes and therefore rapidly passes from the blood to the brain. Clonazepam causes decreased inhibition, reduced anxiety, and a loss of voluntary muscle control. In addition, it causes anterograde amnesia, impairing the victim‟s memory of events occurring shortly after ingestion of the drug. These qualities may make clonazepam attractive to potential sexual offenders. Another fact that makes clonazepam particularly dangerous as a date-rape drug is that it is sometimes sold under the same street name „Roofies‟ as flunitrazepam.

5.3 Lysergic Acid Diethylamide (LSD) The LSD is structurally related to serotonin (5-hydroxytryptamine) and is an agonist at the 5- HT1 receptor. Serotonin modulates many psychological and physiological processes including mood, personality, affect, appetite, sexual desire, motor function, temperature regulation, pain perception, and sleep induction. LSD inhibits central raphe neurons of brainstem through stimulation of 5-HT1A receptors, which are coupled to Adenylcyclase. LSD is also an agonist at 5-HT2A, 2C receptors, which are not located presynaptically on serotonergic cell bodies but on certain subpopulations of neurons in postsynaptic regions. The majority of 5-HT2 receptors in the brain are located in the cerebral cortex. Animal experiments have shown that LSD is anatomically distributed maximally in the visual and auditory cortex, and the limbic cortex (besides the pituitary, pineal, and hypothalamic areas), which parallels the finding of high concentration of 5-HT2 receptors in human cerebral cortex.

5.4 Ketamine The pharmacology of ketamine is complex. Like Phencyclidine, ketamine has activity at multiple sites in the brain. It primarily acts as a glutamate antagonist by non-competitively binding to the PCP receptor located in the ion channel of the N-methyl-d-aspartate (NMDA) receptor complex. It sterically blocks the cation channel gated by the NMDA receptor, impeding the flow of Na+ and Ca+2 ions into the neuron and resulting in disruption of glutamate-mediated transmission at these sites throughout the brain. The (S)-isomer is more potent in displacing the NMDA ligand from its receptor than is (R)-ketamine. In addition, ketamine facilitates monoamine transmission by inhibiting the reuptake of dopamine, noradrenaline (norepinephrine) and serotonin, resulting in an accumulation of these neurotransmitters in synapses. It also acts on the opiate system as an agonist at the μ-opiate receptor. Ketamine is rapidly metabolised, with the principal metabolites being an active metabolite, norketamine, and an inactive metabolite, 6-hydroxynorketamine. Ketamine is demethylated to norketamine by the liver microsomal cytochrome P450 system.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

5.5 Methylenedioxymethamphetamine (MDMA) The main pharmacological effect of MDMA is an increase in secretion and inhibition of re- uptake of serotonin, dopamine and norepinephrine in the brain. MDMA causes , a feeling of empathy, increased energy and tactile sensation. In some cases MDMA can cause mild stimulation and severe stimulation similar to that of . MDMA can impair judgement, resulting in dangerous behaviour. The short-term health risks associated with taking MDMA include hypertension, hyperthermia and dehydration, while the main long- term effect includes severe depression due to permanent disruption of serotonin production in the CNS.

5.6 Alcohol and other drugs Other sedative drugs associated with drug facilitated sexual assault include scopolamine, barbiturates, and muscle relaxants such as , cyclobenzaprine and Meprobamate, diphenhydramine and other benzodiazepines. Drugs used in drug facilitated sexual assault have depressant effects on their users. Symptoms reported by victims of alleged drug- facilitated rape include confusion, decreased heart rate, dizziness, drowsiness, impaired judgement, impaired memory, lack of muscle control, loss of consciousness, nausea, reduced blood pressure and reduced inhibition. All these effects can be synergistically enhanced if the drug is taken with alcohol. In addition, drugs used in drug facilitated sexual assault induced amnesia, presumably one of the main reasons for their selection as „date-rape‟ drugs.

6. Identification of Date Rape Drugs

 MARQUIS REAGENT TEST

Preparation of reagent- To the 1ml of Formaldehyde solution, few drops of conc. Sulphuric Acid is added and stock solution is prepared. Procedure:

 Few drops of sample are placed in spot plate.  Then 2-3 drops of stock solution is poured on the plated

Result:

 Blue- Black Colour for both MDMA  Orange colour change to brown colour, which finally changes to purple, indicates the presence of LSD.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

 SIMON'S REAGENT TEST

Preparation of reagent: Solution A: 20% aqueous Sodium Carbonate solution. Solution B: 50% ethanolic Acetaldehyde solution. Solution C: 1% aqueous Sodium Nitroprusside solution. Procedure:

 Appropriate amount of sample is taken on spot plate  A drop of Solution A is added followed by one drop of Solution B.  Further, few drops of Solution C is added.

Result: Appearance of blue colour indicates the positive tests for the presence of while appearance of slow pink to cherry red colour indicates the presence of .

 LIEBERMANN’S TEST

Preparation of reagent: 5 gram of Sodium Nitrite is added in 50 ml. of Sulphuric Acid. Procedure:

 To the sample, reagent is added drop wise.

Result: Red- Orange colour indicates the presence of .

 MANDELIN’S REAGENT TEST

Preparation of reagent: 1 gram Ammonium Vanadate is dissolved in 100ml. concentrated Sulphuric Acid.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

Procedure:

 Appropriate amount of aqueous solution is taken.  Few drops of Mandelin‟s reagent is added

Result: Appearance of green colour darkens rapidly indicates the positive test for the presence of amphetamines. On stirring the colour passes through several shades to emerald green and dark reddish brown, which changes to light red-brown on heating.

 COBALT NITRATE TEST Preparation of reagent: 1% Cobalt Nitrate solution Procedure: As similar to above

Result: Pink-to-violet colour is indicative of GHB.

 EHRLICH REAGENT TEST

Preparation of reagent: 1g para-dimethylamine benzaldehyde (p-DMAB) in is dissolved in10ml Methanol and 10ml conc. Ortho Phosphoric Acid is added further.

Procedure: Take appropriate amount of the sample or few drops of methanol extract of the sample in a depression spot plate and add two drops of Ehrlich reagent. Appearance of a blue to purple colour indicates the presence of LSD.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

 FROHDE’S REAGENT TEST

Preparation of reagent: 50 mgs of molybdic acid or Sodium Molybdate is dissolved in 10 ml of hot concentrated Sulphuric Acid. The resulting solution should be colourless.

Procedure: Take appropriate amount of the sample or few drops of Frohde‟s Reagent. Olive green changes to blue, which changes to green indicating the presence of LSD.

 MECKE’S REAGENT TEST

Preparation of reagent: 0.25 gms of Selenious Acid is dissolved in 25 ml of concentrated Sulphuric Acid

Procedure: Take appropriate amount of the sample or few drops of Mecke‟s Reagent. Orange colour indicating the presence of Mescaline and Green colour changing to Blue-Purple indicates the presence of MDA.

7. Summary

 Drug Facilitated Sexual Assault (DFSA) also called Date-Rape is defined as the voluntary or involuntary ingestion of a drug by a victim that results in an act of sexual activity without consent.

 Drug-facilitated sexual assault, or the use of so-called „„date-rape‟‟ drugs, is a crime in which the executor secretly administers drugs (usually through alcoholic drinks) to the victim prior to a sexual assault. The drugs work in a way that renders the victim physically helpless and unable to remember what has happened.

 There are three well-known date-rape drugs: GHB (gamma hydroxybutyrate), Rohypnol (flunitrazepam) and Ketamine (ketamine hydrochloride).

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs

 Flunitrazepam (Rohypnol or Roofies) has become popular as a drug of abuse, often combined with alcohol, marijuana, or cocaine to produce an intense “high”. It has been used as a “date rape” drug, both for its properties of lowering inhibitions and because it can cause retrograde amnesia.

 Apart from being misused as a Date- Rape Drug, Ketamine, is an anaesthetic for humans and for animals and GHB is also used to treat sleep problems.

 For the ideal analysis of the date-rape drugs, the main responsibilities to be deliberated are:

(a) Determination of the presence a controlled substance, (b) Determination of amount of the substance, and (c) Determination of the relationship of drug samples to each other through comparison or profiling.

 A number of methods have been developed to determine these drugs, most focus is on the application of Gas Chromatography- Mass Spectrometry (GC/MS), Liquid Chromatography-Mass Spectrometry (LC/MS) or Capillary Electrophoresis/ Mass Spectrometry (CE/MS) for their determination in serum or biologically related samples.

FORENSIC SCIENCE PAPER No. 9: Drugs of Abuse MODULE No. 24: Date Rape Drugs