Propylhexedrine
Encyclopedia
Propylhexedrine is a stimulant
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...

 drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...

 related to methamphetamine
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...

. It is used mainly to provide temporary symptomatic relief of nasal congestion due to colds
Common cold
The common cold is a viral infectious disease of the upper respiratory system, caused primarily by rhinoviruses and coronaviruses. Common symptoms include a cough, sore throat, runny nose, and fever...

, allergies
Allergy
An Allergy is a hypersensitivity disorder of the immune system. Allergic reactions occur when a person's immune system reacts to normally harmless substances in the environment. A substance that causes a reaction is called an allergen. These reactions are acquired, predictable, and rapid...

 and allergic rhinitis
Rhinitis
Rhinitis , commonly known as a stuffy nose, is the medical term describing irritation and inflammation of some internal areas of the nose. The primary symptom of rhinitis is nasal dripping. It is caused by chronic or acute inflammation of the mucous membrane of the nose due to viruses, bacteria or...

. Being a vasoconstrictor used to decongest nasal mucosa, it is administered by inhalation
Inhalation
Inhalation is the movement of air from the external environment, through the air ways, and into the alveoli....

.

Propylhexedrine is most commonly found in over-the-counter Benzedrex inhaler. Benzedrex was first manufactured by Smith, Kline and French after the Benzedrine
Benzedrine
Benzedrine is the trade name of the racemic mixture of amphetamine . It was marketed under this brandname in the USA by Smith, Kline & French in the form of inhalers, starting in 1928...

 inhaler, which contained racemic amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...

, became unavailable following the placement of amphetamines on the U.S. Schedule II
Controlled Substances Act
The Controlled Substances Act was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. The CSA is the federal U.S. drug policy under which the manufacture, importation, possession, use and distribution of certain...

 status (second highest abuse potential with limited medicinal use). Propylhexedrine has also seen use in Europe
Europe
Europe is, by convention, one of the world's seven continents. Comprising the westernmost peninsula of Eurasia, Europe is generally 'divided' from Asia to its east by the watershed divides of the Ural and Caucasus Mountains, the Ural River, the Caspian and Black Seas, and the waterways connecting...

 as an appetite suppressant under the trade name Obesin and in the anticonvulsant
Anticonvulsant
The anticonvulsants are a diverse group of pharmaceuticals used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of bipolar disorder, since many seem to act as mood stabilizers, and in the treatment of neuropathic pain. The goal of an...

 preparation barbexaclone
Barbexaclone
Barbexaclone is a salt compound of phenobarbital and levopropylhexedrine. It was introduced in 1983. It has been reported to be as effective as phenobarbital but better tolerated; however, as of 2004, these "promising results" had not yet been confirmed nor denied in controlled trials...

 its S-isomer (levopropylhexedrine
Levopropylhexedrine
Levopropylhexedrine is a psychostimulant used as an anorectic in Germany. It has also been used in the anticonvulsant preparation barbexaclone in combination with phenobarbital to offset sedation. Levopropylhexedrine is the S-enantiomer of propylhexedrine. It is synthesized from d-methamphetamine....

 or L-propylhexedrine) is bonded with phenobarbital
Phenobarbital
Phenobarbital or phenobarbitone is a barbiturate, first marketed as Luminal by Friedr. Bayer et comp. It is the most widely used anticonvulsant worldwide, and the oldest still commonly used. It also has sedative and hypnotic properties but, as with other barbiturates, has been superseded by the...

 for the purpose of offsetting the barbiturate-induced sedation
Sedation
Sedation is the reduction of irritability or agitation by administration of sedative drugs, generally to facilitate a medical procedure or diagnostic procedure...

. Levopropylhexedrine is also used as an anorectic under the brand name Eventin.

Chemistry

Freebase propylhexedrine is a volatile, oily liquid at room temperature. The slow vaporization of freebase propylhexedrine allows it to be administered via inhalation.

Propylhexedrine can be reacted with an acid like hydrochloric acid
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....

 to form a salt form of propylhexedrine. Propylhexedrine hydrochloride has the appearance of a white powder or crystals.

Propylhexedrine is structurally similar to methamphetamine
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...

. The only difference in the two compounds is that an alicyclic cyclohexyl
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon...

 group is used in lieu of the aromatic phenyl group of methamphetamine. It is because of this that propylhexedrine is not an amphetamine, nor even a phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...

, but instead can be referred to as a cycloalkyl
Cycloalkane
Cycloalkanes are types of alkanes that have one or more rings of carbon atoms in the chemical structure of their molecules. Alkanes are types of organic hydrocarbon compounds that have only single chemical bonds in their chemical structure...

amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...

.

Propylhexedrine, like amphetamine and methamphetamine, is a chiral compound (the α-carbon is chiral, like in its amphetamine cousins). The propylhexedrine contained in Benzedrex inhalers is racemic
Racemic
In chemistry, a racemic mixture, or racemate , is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule. The first known racemic mixture was "racemic acid", which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid.- Nomenclature :A...

 (RS)-propylhexedrine as the freebase
Freebase (chemistry)
Freebase or free base refers to the pure basic form of an amine, as opposed to its salt form. The amine is usually an alkaloid natural product. Free base is commonly used in organic chemistry and pharmaceuticals to describe the unprotonated amine form of a compound.Most alkaloids are unstable in...

. (S)-Propylhexedrine, also known as levopropylhexedrine, is believed to be the more biologically active isomer of the two. (S)-Propylhexedrine can be synthesized from dextro-methamphetamine.

Pharmacology

The pharmacology of propylhexedrine is not understood fully, but it appears to act as an agonist at alpha-adrenergic receptors and it appears to reverse the transporters for dopamine
Dopamine
Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their...

 (DA), norepinephrine
Norepinephrine
Norepinephrine is the US name for noradrenaline , a catecholamine with multiple roles including as a hormone and a neurotransmitter...

 (NE), and serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...

 (5-HT) leading to these monoamines to be released from the vesicle
Vesicle (biology)
A vesicle is a bubble of liquid within another liquid, a supramolecular assembly made up of many different molecules. More technically, a vesicle is a small membrane-enclosed sack that can store or transport substances. Vesicles can form naturally because of the properties of lipid membranes , or...

s to the cytoplasm
Cytoplasm
The cytoplasm is a small gel-like substance residing between the cell membrane holding all the cell's internal sub-structures , except for the nucleus. All the contents of the cells of prokaryote organisms are contained within the cytoplasm...

 and then from the cytoplasm to the synapse
Synapse
In the nervous system, a synapse is a structure that permits a neuron to pass an electrical or chemical signal to another cell...

s. This results in a net increase in levels of these monoamines in the synapses which correlates with increased activity at these receptors. Additionally propylhexedrine appears to antagonize the VMAT2
VMAT2
The vesicular monoamine transporter 2 also known as solute carrier family 18 member 2 is a protein that in humans is encoded by the SLC18A2 gene...

 transporter, leading to a further increase in the aforementioned monoamines. The actions of propylhexedrine in this regard are similar to amphetamine's mode of action.

Contraindications

Propylhexedrine should never be used if an MAOI has been used in the past 14 days or is being currently used as this can lead to a hypertensive crisis. People with cardiac disease should not use propylhexedrine.

Additionally drugs such as stimulants and sympathomimetics should not be taken along with propylhexedrine as this can lead to potentially dangerous spikes in blood pressure
Blood pressure
Blood pressure is the pressure exerted by circulating blood upon the walls of blood vessels, and is one of the principal vital signs. When used without further specification, "blood pressure" usually refers to the arterial pressure of the systemic circulation. During each heartbeat, BP varies...

 and irregular heart rhythms.

Medical use

Propylhexedrine is used for nasal congestion
Nasal congestion
Nasal congestion is the blockage of the nasal passages usually due to membranes lining the nose becoming swollen from inflamed blood vessels. It is also known as nasal blockage, nasal obstruction, blocked nose, stuffy nose, or stuffed up nose.Nasal congestion has many causes and can range from a...

. Historically, it has also been used for weight loss
Weight loss
Weight loss, in the context of medicine, health or physical fitness, is a reduction of the total body mass, due to a mean loss of fluid, body fat or adipose tissue and/or lean mass, namely bone mineral deposits, muscle, tendon and other connective tissue...

.

Recreational use

Propylhexedrine has been reported to be used recreationally, obtained as freebase from the cotton rods that Benzedrex inhalers contain.

Effects

Propylhexedrine has sympathomimetic, adrenergic, vasocontricive and psychostimulant effects when taken above the medical dosage, the effects produced tend to be of the amphetamine type. Effects include increased sweating
Sweating
Perspiration is the production of a fluid consisting primarily of water as well as various dissolved solids , that is excreted by the sweat glands in the skin of mammals...

, talkativeness, euphoria
Euphoria
Euphoria is an emotional and mental state defined as a sense of great elation and well being.Euphoria may also refer to:* Euphoria , a genus of scarab beetles* Euphoria, a genus name previously used for the longan and other trees...

, pupil dilation, emotional lability, anorexia
Anorexia (symptom)
Anorexia is the decreased sensation of appetite...

, tachycardia
Tachycardia
Tachycardia comes from the Greek words tachys and kardia . Tachycardia typically refers to a heart rate that exceeds the normal range for a resting heart rate...

, palpitations, dry mouth, bruxism
Bruxism
Bruxism is characterized by the grinding of the teeth and typically includes the clenching of the jaw. It is an oral parafunctional activity that occurs in most humans at some time in their lives. In most people, bruxism is mild enough not to be a health problem...

, anxiety
Anxiety
Anxiety is a psychological and physiological state characterized by somatic, emotional, cognitive, and behavioral components. The root meaning of the word anxiety is 'to vex or trouble'; in either presence or absence of psychological stress, anxiety can create feelings of fear, worry, uneasiness,...

, dysphoria
Dysphoria
Dysphoria is medically recognized as a mental and emotional condition in which a person experiences intense feelings of depression, discontent and indifference to the world around them.Mood disorders can induce dysphoria, often with a heightened risk of suicide, especially in...

, increased aggressiveness, paranoia
Paranoia
Paranoia [] is a thought process believed to be heavily influenced by anxiety or fear, often to the point of irrationality and delusion. Paranoid thinking typically includes persecutory beliefs, or beliefs of conspiracy concerning a perceived threat towards oneself...

, headache
Headache
A headache or cephalalgia is pain anywhere in the region of the head or neck. It can be a symptom of a number of different conditions of the head and neck. The brain tissue itself is not sensitive to pain because it lacks pain receptors. Rather, the pain is caused by disturbance of the...

, dizziness
Dizziness
Dizziness refers to an impairment in spatial perception and stability. The term is somewhat imprecise. It can be used to mean vertigo, presyncope, disequilibrium, or a non-specific feeling such as giddiness or foolishness....

, slurred or impaired speech, rarely convulsions, serious heart
Heart
The heart is a myogenic muscular organ found in all animals with a circulatory system , that is responsible for pumping blood throughout the blood vessels by repeated, rhythmic contractions...

 problems; psychosis
Psychosis
Psychosis means abnormal condition of the mind, and is a generic psychiatric term for a mental state often described as involving a "loss of contact with reality"...

 can occur.

Withdrawal
Withdrawal
Withdrawal can refer to any sort of separation, but is most commonly used to describe the group of symptoms that occurs upon the abrupt discontinuation/separation or a decrease in dosage of the intake of medications, recreational drugs, and alcohol...

 effects can occur and include fatigue, depression
Depression (mood)
Depression is a state of low mood and aversion to activity that can affect a person's thoughts, behaviour, feelings and physical well-being. Depressed people may feel sad, anxious, empty, hopeless, helpless, worthless, guilty, irritable, or restless...

, suicidal tendencies
Suicidal tendencies
Suicidal tendencies is the propensity for a person to have suicidal ideation or to make suicide attempts. It may also refer to:* Suicidal Tendencies, a band that was founded in Venice, Los Angeles, California, in 1981 by the leader and only permanent member, singer Mike Muir* Suicide, the act of a...

, hunger
Hunger
Hunger is the most commonly used term to describe the social condition of people who frequently experience the physical sensation of desiring food.-Malnutrition, famine, starvation:...

 and extreme desire for sleep
Sleep
Sleep is a naturally recurring state characterized by reduced or absent consciousness, relatively suspended sensory activity, and inactivity of nearly all voluntary muscles. It is distinguished from quiet wakefulness by a decreased ability to react to stimuli, and is more easily reversible than...

.

Recreational use potential

Propylhexedrine has a lower potential for abuse than other stimulants. This is partially because methods of its use are limited, unlike more commonly abused amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...

, methamphetamine
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...

 and methylphenidate
Methylphenidate
Methylphenidate is a psychostimulant drug approved for treatment of attention-deficit hyperactivity disorder, postural orthostatic tachycardia syndrome and narcolepsy. It may also be prescribed for off-label use in treatment-resistant cases of lethargy, depression, neural insult and obesity...

. Oral ingestion being the most practical method of consumption, the inactive ingredients in a Benzedrex inhaler (menthol
Menthol
Menthol is an organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is -menthol, which is assigned...

 and lavender oil
Lavender oil
Lavender oil is an essential oil obtained by distillation from the flower spikes of certain species of lavender. Two forms are distinguished, lavender flower oil, a colorless oil, insoluble in water, having a density of 0.885 g/mL; and lavender spike oil, a distillate from the herb Lavandula...

) are also ingested - most users report the taste and smell to be very unpleasant, resulting in "menthol burps" (frequent belching releasing the smell of the two) that often cause the user discomfort and sometimes nausea. Many drug users find that propylhexedrine has a very heavy "comedown" compared to the "high" it causes. The abuse potential is considered to be low enough that neither the DEA
Drug Enforcement Administration
The Drug Enforcement Administration is a federal law enforcement agency under the United States Department of Justice, tasked with combating drug smuggling and use within the United States...

 nor the WHO
Who
Who may refer to:* Who , an English-language pronoun* who , a Unix command* Who?, one of the Five Ws in journalism- Art and entertainment :* Who? , a 1958 novel by Algis Budrys...

 consider it a drug of concern at the present, unlike ephedrine
Ephedrine
Ephedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia....

 and its salts which are known to be used as precursor chemicals in illicit manufacture of methamphetamine (and occasionally amphetamine). That said, propylhexedrine is controlled in some jurisdictions.

Injection risks

While propylhexedrine is limited in a number of administration routes, attempts to extract the drug from the nasal inhaler and then inject it have been reported. Recreational use by injection is dangerous and could result in serious bodily harm or death. IV use of propylhexedrine is known to cause transient diplopia
Diplopia
Diplopia, commonly known as double vision, is the simultaneous perception of two images of a single object that may be displaced horizontally, vertically, or diagonally in relation to each other...

 and brainstem dysfunction, and deaths have been recorded in the medical literature. Typically, recorded cases of IV use are prepared by forming propylhexedrine HCl
Hydrochloride
In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....

 in a solution with hydrochloric acid, the solution is then heated to evaporate and the resulting crystals are dissolved in water for injection.

Drug risks

As with similar drugs, using propylhexedrine to keep oneself awake for extended amounts of time can lead to a temporary state of sleep deprivation
Sleep deprivation
Sleep deprivation is the condition of not having enough sleep; it can be either chronic or acute. A chronic sleep-restricted state can cause fatigue, daytime sleepiness, clumsiness and weight loss or weight gain. It adversely affects the brain and cognitive function. Few studies have compared the...

 during which an individual may experience hallucinations including auditory, visual and tactile (e.g. bugs crawling on or under the skin
Formication
Formication is the medical term for a sensation that resembles that of insects crawling on the skin. It is one specific form of a set of sensations known as paresthesia, which also include the more common prickling, tingling sensation of "pins and needles"...

), paranoia
Paranoia
Paranoia [] is a thought process believed to be heavily influenced by anxiety or fear, often to the point of irrationality and delusion. Paranoid thinking typically includes persecutory beliefs, or beliefs of conspiracy concerning a perceived threat towards oneself...

, irritability
Irritability
Irritability is an excessive response to stimuli. The term is used for both the physiological reaction to stimuli and for the pathological, abnormal or excessive sensitivity to stimuli; It is usually used to refer to anger or frustration....

 and impaired memory.

Propylhexedrine, being a vasocontrictor and a stimulant, may carry a further risk as blood pressure and heart rate are raised, sometimes severely. Hypertension
Hypertension
Hypertension or high blood pressure is a cardiac chronic medical condition in which the systemic arterial blood pressure is elevated. What that means is that the heart is having to work harder than it should to pump the blood around the body. Blood pressure involves two measurements, systolic and...

 experienced by users of propylhexedrine can be dangerous, especially in those who have pre-existing blood pressure problems. The increase in heart rate can lead to lower levels of oxygen, discomfort, panic and in severe cases heart attack or serious arrhythmias. Again, this risk is higher if the user has existing heart problems.

Using propylhexedrine by ingesting the cotton rod contained in the Benzedrex inhaler may be dangerous. It appears that the cotton typically goes completely through the gastrointestinal tract and is then excreted, but there is the possibility of it causing an intestinal obstruction which is a medical emergency and can lead to infection and death. Currently there is no report of obstruction that occurred due to ingesting the Benzedrex cotton rod.

See also

  • Amphetamine
    Amphetamine
    Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...

  • Benzedrine
    Benzedrine
    Benzedrine is the trade name of the racemic mixture of amphetamine . It was marketed under this brandname in the USA by Smith, Kline & French in the form of inhalers, starting in 1928...

  • Cyclopentamine
    Cyclopentamine
    Cyclopentamine is a sympathomimetic alkylamine, classified as a vasoconstrictor...

  • Cypenamine
    Cypenamine
    Cypenamine, or phenylcyclopentamine, is a stimulant drug. It is currently known only in scientific research and has never been developed for market use. The trans- isomer is reported to be more active than the racemate...

  • Methamphetamine
    Methamphetamine
    Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...

  • Tranylcypromine
    Tranylcypromine
    Tranylcypromine is a drug of the substituted phenethylamine and amphetamine classes which acts as a monoamine oxidase inhibitor —it is a non-selective and irreversible inhibitor of the enzyme monoamine oxidase...

The source of this article is wikipedia, the free encyclopedia.  The text of this article is licensed under the GFDL.
 
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