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Rohypnol

From ChemWiki
Rohypnol
Rohypnol
General
Systematic name 6-(2-fluorophenyl)-2-methyl-9-nitro-2,

5-diazabicyclo[5.4.0]undeca-5,8,10,12- tetraen-3-one

Molecular formula C16H12FN3O3
Molar mass 313.3
Appearance White, light yellow crystalline powder
CAS number 1622-62-4
Properties
Solubility Almost insoluble in water but soluble in alcohol
Melting point 168-172 C

Rohypnol (Flunitrazepam)


Rohypnol is a sedative and belongs to a class of drugs known as the benzodiazepines which depress the central nervous system. It is the trade name for a compound known as flunitrazepam. The drug can be taken in a pill (1 and 2mg), crushed up and snorted or dissolved in a drink (alcohol). Rohypnol is manufactured worldwide for medical and therapeutic use but its popularity amongst drug users has rapidly increased and thus is referred to as a ‘Club Drug’ along with Ketamine, LSD and MDMA.

Synthesis

Flunitrazepam was first synthesised from (2-fluoro)-methylbenzene.

Mechanism of action

Rohypnol is lipophlic and when it is ingested, it is absorbed quickly into the bloodstream and enters the brain via oxidative pathways. The chemical is metabolised rapidly by enzymes (main one being CYP3A4) and binds to nerve receptors that are involved in co-ordination, memory and anxiety. In the absence of Rohypnol, the GABA neurotransmitter binds to these nerve receptors and reduces the activity in the brain. However, when Rohypnol is present it binds to another site (not the binding site) of GABA which slows down the nerve activity in the brain more efficiently. This enhancement of the GABA effect makes Rohypnol a ‘positive allosteric modulator’.

As mentioned previously, Rohypnol is very rapidly absorbed and carried hepatically around the body and peak plasma concentrations occur after 40 minutes from ingestion and thus are a very fast acting benzodiazepine. In addition, Rohypnol has a long half life (roughly 18-26 hours) and a long lasting active metabolite so its effects can persist through to the next day.

Uses

Recreational Rohypnol is grossly misused recreationally both on its own and with other drugs, e.g. with heroin to heighten the effects or after cocaine or methamphetamine use to ease the after effects of the high. It is also used to counteract the unwanted effects of stimulants such as paranoia, jitteriness, etc. It is used most frequently at raves and by high school and university students. Its low cost and availability is responsible for the rapidly growing numbers of Rohypnol users. Medical In the early 1970s, this drug was first used in hospitals where deep sedation was required. It is prescribed to relieve severe back pain and in the short term treatments of extreme cases of sleep disorders. It is also used therapeutically to calm patients.

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Description


Effects

As Rohypnol affects the neutosteroid metabolism, it interferes with brain and reproductive system functions. It results in changes to emotional state and motor functions. There are many short term effects from taking Rohypnol, the most common being amnesia. Others include: muscle relaxation, loss of inhibition, ‘drunken’ feeling, reduction in anxiety and hypnotic and euphoric effects. There are also adverse affects such as excessive sedation, impairment of balance and speech, lack of concentration, confusion, hallucinations, impaired psychomotor functions, slurred speech, and gastrointestinal distrurbances. Although it is classed as a depressant, in some individuals it may lead to aggressive behaviour or excitability.

Risks

It can be slipped into a drink unnoticed as it is odourless, tasteless and cannot be seen. There is therefore a high risk of a sexual assault and thus this drug is commonly known as the ‘date-rape drug’. As the drug slows down the breathing and heart rate it can lead to breathing difficulties and nausea. The addictive nature of Rohypnol means that regular users are likely to develop a physical dependence. In addition, individuals may also develop a psychological dependence and overtime, increased doses are required to produce the same effect. Withdrawal effects are therefore inevitable and with heavy users, abrupt withdrawal can result in psychosis, seizures, severe insomnia and anxiety. When it is mixed with other drugs the adverse effects are heightened and the possibility of overdose is increased. Overdose can lead to excessive sedation, respiratory arrest which it most serious cases can result in coma and death. Comas and seizures are most likely when this sedative is combined with amphetamines. When it is used during pregnancy, the lipolphilic Rohypnol penetrates the membranes and thus crosses over into the placenta resulting in a syndrome known as ‘Floppy Infant Syndrome’ when present in high doses.

Detection

Amnesia induced by taking this drug means that a victim of date-rape would not be able to provide any information about events that occurred whilst they were under its influence. This is the reason why the use of this drug in sexual assault is so common. The long half life of the drug means that sophisticated technological equipment can detect flunitrazepan and its related compounds in urine samples for up to about 5 days and roughly 30 days in hair.

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Mass Spectrum Chromatogram
Description
Description


Legal status

Rohypnol is a class C drug. It is legal in 60 countries worldwide for medical use. It is available in the UK on private prescription otherwise its possession is illegal. Rohypnol is not legally available even for medical use in the US. In 1998, the manufacturing company (Hoffman-Roche) improved the formula of the drug to make it easier to detect. It now contains a blue dye which appears when it is added to a drink and its solubility properties are altered such that it takes longer for it to dissolve into a drink.

Other names

Circles, Roach-2, Roofies, Roopies, Rope, R-2, Roaches, Forget-me-pills, Mexican Valium, Baptist Communion, R2-Do-U.

References