Pseudoephedrine (PSE) is a
sympathomimetic
Sympathomimetic drugs (also known as adrenergic drugs and adrenergic amines) are stimulant compounds which mimic the effects of endogenous agonists of the sympathetic nervous system. Examples of sympathomimetic effects include increases in hea ...
drug
A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via inhala ...
of the
phenethylamine and
amphetamine chemical class Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classificati ...
es. It may be used as a
nasal/sinus decongestant,
as a
stimulant
Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
, or as a
wakefulness-promoting agent in higher doses.
It was first characterized in 1889 by the German chemists
Ladenburg and Oelschlägel, who used a sample that had been isolated from ''
Ephedra vulgaris'' by the Merck pharmaceutical corporation of Darmstadt, Germany. The
salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many
over-the-counter
Over-the-counter (OTC) drugs are medicines sold directly to a consumer without a requirement for a prescription from a healthcare professional, as opposed to prescription drugs, which may be supplied only to consumers possessing a valid prescr ...
preparations
''Preparations'' is a studio album by Prefuse 73
Guillermo Scott Herren is an American producer who has been based in Atlanta, Barcelona and New York City. Herren releases music under the aliases Prefuse 73, Delarosa & Asora, Ahmad Szabo, a ...
, either as a single ingredient or (more commonly) in a fixed-dose combination with one or more additional active ingredients such as
antihistamine
Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic (not patented) drug that can be bought without a prescription and provide ...
s,
guaifenesin,
dextromethorphan
Dextromethorphan (DXM) is a medication most often used as a cough suppressant in over-the-counter cold and cough medicines. It is sold in syrup, tablet, spray, and lozenge forms. In 2022, the FDA approved a formulation of it combined with b ...
,
paracetamol (acetaminophen) or an
NSAID (such as
aspirin
Aspirin, also known as acetylsalicylic acid (ASA), is a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and/or inflammation, and as an antithrombotic. Specific inflammatory conditions which aspirin is used to treat inc ...
or
ibuprofen).
Medical uses
Pseudoephedrine is a
stimulant
Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
, but it is well known for shrinking swollen nasal mucous membranes, so it is often used as a
decongestant. It reduces tissue
hyperemia,
edema
Edema, also spelled oedema, and also known as fluid retention, dropsy, hydropsy and swelling, is the build-up of fluid in the body's tissue. Most commonly, the legs or arms are affected. Symptoms may include skin which feels tight, the area ma ...
, and
nasal congestion commonly associated with
colds or
allergies. Other beneficial effects may include increasing the drainage of
sinus secretions, and opening of obstructed
Eustachian tubes. The same
vasoconstriction
Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels, in particular the large arteries and small arterioles. The process is the opposite of vasodilation, the widening of blood vess ...
action can also result in
hypertension
Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high b ...
, which is a noted side effect of pseudoephedrine.
Pseudoephedrine can be used either as oral or as
topical decongestant. Due to its stimulating qualities, however, the oral preparation is more likely to cause adverse effects, including
urinary retention. According to one study, pseudoephedrine may show effectiveness as an
antitussive drug (suppression of
cough).
Pseudoephedrine is indicated for the treatment of nasal congestion, sinus congestion and Eustachian tube congestion.
[Bicopoulos D, editor. AusDI: Drug information for the healthcare professional, 2nd edition. Castle Hill: Pharmaceutical Care Information Services; 2002.] Pseudoephedrine is also indicated for
vasomotor rhinitis, and as an adjunct to other agents in the optimum treatment of
allergic rhinitis
Allergic rhinitis, of which the seasonal type is called hay fever, is a type of inflammation in the nose that occurs when the immune system overreacts to allergens in the air. Signs and symptoms include a runny or stuffy nose, sneezing, red, ...
,
croup
Croup, also known as laryngotracheobronchitis, is a type of respiratory infection that is usually caused by a virus. The infection leads to swelling inside the trachea, which interferes with normal breathing and produces the classic symptoms ...
,
sinusitis,
otitis media
Otitis media is a group of inflammatory diseases of the middle ear. One of the two main types is acute otitis media (AOM), an infection of rapid onset that usually presents with ear pain. In young children this may result in pulling at the ear, ...
, and
tracheobronchitis.
Pseudoephedrine is also used as a first-line prophylactic for recurrent
priapism.
Erection is largely a
parasympathetic response, so the sympathetic action of pseudoephedrine may serve to relieve this condition. Treatment for
urinary incontinence is an
off-label use ("unlabeled use") for these medications.
Adverse effects
Common adverse drug reactions (ADRs) associated with pseudoephedrine therapy include
central nervous system
The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain and spinal cord. The CNS is so named because the brain integrates the received information and coordinates and influences the activity of all p ...
stimulation, insomnia, nervousness, excitability, dizziness and anxiety. Infrequent ADRs include
tachycardia or
palpitation
Palpitations are perceived abnormalities of the heartbeat characterized by awareness of cardiac muscle contractions in the chest, which is further characterized by the hard, fast and/or irregular beatings of the heart.
Symptoms include a rap ...
s. Rarely, pseudoephedrine therapy may be associated with
mydriasis (dilated pupils),
hallucinations,
arrhythmias,
hypertension
Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high b ...
, seizures and
ischemic colitis
Ischemic colitis (also spelled ischaemic colitis) is a medical condition in which inflammation and injury of the large intestine result from inadequate blood supply. Although uncommon in the general population, ischemic colitis occurs with greater ...
;
[Rossi S, editor. ]Australian Medicines Handbook
Australian Medicines Handbook (AMH) is a peer-reviewed medicines prescribing guide for Australian health professionals. The handbook is available in paper and digital formats and is supplemented by the ''AMH Aged Care Companion'' and the ''AMH C ...
2006. Adelaide: Australian Medicines Handbook; 2006. as well as severe skin reactions known as recurrent pseudo-scarlatina, systemic contact dermatitis, and nonpigmenting
fixed drug eruption. Pseudoephedrine, particularly when combined with other drugs including narcotics, may also play a role in the precipitation of episodes of paranoid
psychosis
Psychosis is a condition of the mind that results in difficulties determining what is real and what is not real. Symptoms may include delusions and hallucinations, among other features. Additional symptoms are incoherent speech and behavi ...
. It has also been reported that pseudoephedrine, among other
sympathomimetic
Sympathomimetic drugs (also known as adrenergic drugs and adrenergic amines) are stimulant compounds which mimic the effects of endogenous agonists of the sympathetic nervous system. Examples of sympathomimetic effects include increases in hea ...
agents, may be associated with the occurrence of
stroke
A stroke is a disease, medical condition in which poor cerebral circulation, blood flow to the brain causes cell death. There are two main types of stroke: brain ischemia, ischemic, due to lack of blood flow, and intracranial hemorrhage, hemorr ...
.
Precautions and contraindications
Pseudoephedrine is contraindicated in patients with
diabetes mellitus
Diabetes, also known as diabetes mellitus, is a group of metabolic disorders characterized by a high blood sugar level ( hyperglycemia) over a prolonged period of time. Symptoms often include frequent urination, increased thirst and increased ...
,
cardiovascular disease, severe or uncontrolled
hypertension
Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high b ...
, severe
coronary artery disease
Coronary artery disease (CAD), also called coronary heart disease (CHD), ischemic heart disease (IHD), myocardial ischemia, or simply heart disease, involves the reduction of blood flow to the heart muscle due to build-up of atherosclerotic pl ...
,
prostatic hypertrophy,
hyperthyroidism
Hyperthyroidism is the condition that occurs due to excessive production of thyroid hormones by the thyroid gland. Thyrotoxicosis is the condition that occurs due to excessive thyroid hormone of any cause and therefore includes hyperthyroidis ...
,
closed angle glaucoma
Glaucoma is a group of eye diseases that result in damage to the optic nerve (or retina) and cause vision loss. The most common type is open-angle (wide angle, chronic simple) glaucoma, in which the drainage angle for fluid within the eye rema ...
, or by pregnant women.
The safety and effectiveness of nasal decongestant use in children is unclear.
Interactions
Concomitant or recent (previous fourteen days)
monoamine oxidase inhibitor use can lead to hypertensive reactions, including
hypertensive crises
Severely elevated blood pressure (equal to or greater than a systolic 180 or diastolic of 120—sometimes termed malignant or accelerated hypertension) is referred to as a hypertensive crisis, as blood pressure at this level confers a high risk ...
.
The antihypertensive effects of
methyldopa
Methyldopa, sold under the brand name Aldomet among others, is a medication used for high blood pressure. It is one of the preferred treatments for high blood pressure in pregnancy. For other types of high blood pressure including very high bl ...
,
mecamylamine,
reserpine
Reserpine is a drug that is used for the treatment of high blood pressure, usually in combination with a thiazide diuretic or vasodilator. Large clinical trials have shown that combined treatment with reserpine plus a thiazide diuretic reduces ...
and
veratrum alkaloids may be reduced by
sympathomimetics
Sympathomimetic drugs (also known as adrenergic drugs and adrenergic amines) are stimulant compounds which mimic the effects of endogenous agonists of the sympathetic nervous system. Examples of sympathomimetic effects include increases in heart ...
.
Beta-adrenergic antagonist
Beta blockers, also spelled β-blockers, are a class of medications that are predominantly used to manage abnormal heart rhythms, and to protect the heart from a second heart attack after a first heart attack (secondary prevention). They are al ...
s may also interact with sympathomimetics. Increase of ectopic pacemaker activity can occur when pseudoephedrine is used concomitantly with
digitalis.
Antacids increase the rate of pseudoephedrine absorption, while
kaolin
Kaolinite ( ) is a clay mineral, with the chemical composition Al2 Si2 O5( OH)4. It is an important industrial mineral. It is a layered silicate mineral, with one tetrahedral sheet of silica () linked through oxygen atoms to one octahedra ...
decreases it.
Mechanism of action
Pseudoephedrine is a sympathomimetic
amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent ...
. Its principal mechanism of action relies on its direct action on the
adrenergic receptor system.
The
vasoconstriction
Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels, in particular the large arteries and small arterioles. The process is the opposite of vasodilation, the widening of blood vess ...
that pseudoephedrine produces is believed to be principally an α-adrenergic receptor response.
Pseudoephedrine acts on α- and β2-adrenergic receptors, to cause vasoconstriction and relaxation of smooth muscle in the bronchi, respectively.
α-Adrenergic receptors are located on the muscles lining the walls of blood vessels. When these receptors are activated, the muscles contract, causing the blood vessels to constrict (vasoconstriction). The constricted blood vessels now allow less fluid to leave the blood vessels and enter the nose, throat and sinus linings, which results in decreased inflammation of nasal membranes, as well as decreased mucus production. Thus, by constriction of blood vessels, mainly those located in the nasal passages, pseudoephedrine causes a decrease in the symptoms of nasal congestion. Activation of β2-adrenergic receptors produces relaxation of smooth muscle of the bronchi,
causing bronchial dilation and in turn decreasing congestion (although not fluid) and difficulty breathing.
Other uses
There have been reports of off-label uses of pseudoephedrine for its stimulant properties. Long-distance truck drivers and athletes, for example, have reportedly used pseudoephedrine as a stimulant to increase their state of alertness/awareness.
A study has also found that pseudoephedrine can reduce milk production in breastfeeding women.
Manufacture of amphetamines
Its membership in the
amphetamine class has made pseudoephedrine a sought-after
chemical precursor
In chemistry, a precursor is a compound that participates in a chemical reaction that produces another compound.
In biochemistry, the term "precursor" often refers more specifically to a chemical compound preceding another in a metabolic pathway, ...
in the
illicit manufacture of
methamphetamine and
methcathinone. As a result of the increasing regulatory restrictions on the sale and distribution of pseudoephedrine, many pharmaceutical firms have reformulated, or are in the process of reformulating medications to use alternative, but less effective,
decongestants, such as
phenylephrine.
In the United States, federal laws control the sale of pseudoephedrine-containing products.
[ ] Many retailers in the US have created corporate policies restricting the sale of pseudoephedrine-containing products. Their policies restrict sales by limiting purchase quantities and requiring a minimum age and government issued photographic identification.
These requirements are similar to and sometimes more stringent than existing law. Internationally, pseudoephedrine is listed as a
Table I precursor under the
.
Sports
Pseudoephedrine was on the
International Olympic Committee's (IOC) banned substances list until 2004, when the
World Anti-Doping Agency (WADA) list replaced the IOC list. Although WADA initially only ''monitored'' pseudoephedrine, it went back onto the "banned" list on January 1, 2010.
Pseudoephedrine is excreted through urine, and concentration in urine of this drug shows a large inter-individual spread; that is, the same dose can give a vast difference in urine concentration for different individuals. Pseudoephedrine is approved to be taken up to 240 mg per day. In seven healthy male subjects this dose yielded a urine concentration range of 62.8 to 294.4 microgram per milliliter (µg/mL) with mean ± standard deviation 149 ± 72 µg/mL. Thus, normal dosage of 240 mg pseudoephedrine per day can result in urine concentration levels exceeding the limit of 150 µg/mL set by WADA for about half of all users. Furthermore, hydration status does not affect urinary concentration of pseudoephedrine.
Canadian rower
Silken Laumann was stripped of her
1995 Pan American Games team gold medal after testing positive for pseudoephedrine.
In February 2000,
Elena Berezhnaya
Elena Viktorovna Berezhnaya (russian: Елена Викторовна Бережная, born 11 October 1977) is a Russian former pair skater. With partner Anton Sikharulidze, she is the 1998 and 1999 World champion, 1998 Olympic silver medal ...
and
Anton Sikharulidze won gold at the
2000 European Figure Skating Championships
The 2000 European Figure Skating Championships was a senior international figure skating competition in the 1999–2000 season. Medals were awarded in the disciplines of men's singles, ladies' singles, pair skating, and ice dancing. The event ...
but were stripped of their medals after Berezhnaya tested positive. This resulted in a three-month disqualification from the date of the test, and the medal being stripped.
She stated that she had taken cold medication approved by a doctor but had failed to inform the ISU as required.
The pair missed the World Championships that year as a result of the disqualification.
Romanian gymnast
Andreea Răducan
Andreea Mădălina Răducan (; born 30 September 1983) is a retired gymnast from Bârlad, Romania. She currently works as a sports announcer and journalist.
Răducan began competing in gymnastics at a young age and was training at the Romanian j ...
was stripped of her gold medal at the
2000 Summer Olympic Games after testing positive. She took two pills given to her by the team coach for a cold. Although she was stripped of the overall gold medal, she kept her other medals, and, unlike in most other doping cases, was not banned from competing again; only the team doctor was banned for a number of years.
Ion Ţiriac
An ion () is an atom or molecule with a net electrical charge.
The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...
, the president of the Romanian Olympic Committee, resigned over the scandal.
In the
2010 Winter Olympic Games, the IOC issued a reprimand against the Slovak
ice hockey
Ice hockey (or simply hockey) is a team sport played on ice skates, usually on an ice skating rink with lines and markings specific to the sport. It belongs to a family of sports called hockey. In ice hockey, two opposing teams use ice ...
player
Lubomir Visnovsky for usage of pseudoephedrine.
In the
2014 Winter Olympic Games Team Sweden and
Washington Capitals ice hockey player
Nicklas Bäckström was prevented from playing in the final for usage of pseudoephedrine. Bäckström claimed he was using it as allergy medication. In March 2014, the IOC Disciplinary Commission decided that Bäckström would be awarded the silver medal.
In January 2015 Bäckström, the IOC, WADA and the
IIHF agreed to a settlement in which he accepted a reprimand but was cleared of attempting to enhance his performance.
Detection of use
Pseudoephedrine may be quantified in blood, plasma, or urine to monitor any possible performance-enhancing use by athletes, confirm a diagnosis of poisoning, or to assist in a medicolegal death investigation. Many commercial
immunoassay
An immunoassay (IA) is a biochemical test that measures the presence or concentration of a macromolecule or a small molecule in a solution through the use of an antibody (usually) or an antigen (sometimes). The molecule detected by the immunoa ...
screening tests directed at the amphetamines cross-react appreciably with pseudoephedrine, but
chromatographic
In chemical analysis, chromatography is a laboratory technique for the separation of a mixture into its components. The mixture is dissolved in a fluid solvent (gas or liquid) called the ''mobile phase'', which carries it through a system (a ...
techniques can easily distinguish pseudoephedrine from other phenethylamine derivatives. Blood or plasma pseudoephedrine concentrations are typically in the 50–300 µg/L range in persons taking the drug therapeutically, 500–3000 µg/L in people with substance use disorder involving pseudoephedrine, or poisoned patients and 10–70 mg/L in cases of acute fatal overdose.
Chemistry
Pseudoephedrine is a
diastereomer of
ephedrine and is readily
reduced into
methamphetamine or
oxidized
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...
into
methcathinone.
Nomenclatures
The
dextrorotary (+)- or d-
enantiomer is (1''S'',2''S'')-pseudoephedrine, whereas the levorotating (−)- or l- form is (1''R'',2''R'')-pseudoephedrine.
In the outdated
system (+)-pseudoephedrine is also referred to as pseudoephedrine and (−)-pseudoephedrine as pseudoephedrine (in the
Fisher projection then the phenyl ring is drawn at bottom).
Often the system (with
small caps
In typography, small caps (short for "small capitals") are characters typeset with glyphs that resemble uppercase letters (capitals) but reduced in height and weight close to the surrounding lowercase letters or text figures. This is technic ...
) and the d/l system (with
lower-case) are confused. The result is that the dextrorotary d-pseudoephedrine is wrongly named pseudoephedrine and the levorotary l-ephedrine (the diastereomer) wrongly ephedrine.
The IUPAC names of the two enantiomers are (1''S'',2''S'')- respectively (1''R'',2''R'')-2-methylamino-1-phenylpropan-1-ol. Synonyms for both are ''psi''-ephedrine and ''threo''-ephedrine.
Pseudoephedrine is the
International Nonproprietary Name of the (+)-form, when used as pharmaceutical substance.
Society and culture
Brand names
The following is a list of
consumer medicines that either contain pseudoephedrine or have switched to a less-regulated alternative such as
phenylephrine.
*
Actifed
Actifed is a registered trademark for a combination antihistamine and nasal decongestant medication used for cold and allergy symptoms. Actifed was developed in 1958 by Burroughs Wellcome & Company (now part of GlaxoSmithKline), later Haleon.
200 ...
(made by
GlaxoSmithKline) — contains 60 mg pseudoephedrine and 2.5 mg
triprolidine in certain countries.
*Advil Cold & Sinus (made by Pfizer Canada Inc.) — contains 30 mg pseudoephedrine
hydrochloride and 200 mg Ibuprofen.
*
Aleve-D Sinus & Cold (made by
Bayer Healthcare
Bayer AG (, commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of business include pharmaceutica ...
) — contains 120 mg pseudoephedrine
hydrochloride (also 220 mg
naproxen).
*
Allegra-D (made by
Sanofi Aventis) — contains 120 mg of pseudoephedrine hydrochloride (also 60 mg of
fexofenadine).
*
Allerclear-D (made by
Kirkland Signature) — contains 240 mg of pseudoephedrine sulfate (also 10 mg of
loratadine).
*
Benadryl
Benadryl is a brand of various antihistamine medications used to stop allergies, whose content varies in different countries, but which includes some combination of diphenhydramine, acrivastine, and/or cetirizine.
It is sold by Johnson & Johnso ...
Plus (made by
McNeil Consumer Healthcare, a
Johnson & Johnson
Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
company) — contains 60 mg pseudoephedrine hydrochloride (also 8 mg
acrivastine)
*
Cirrus (made by
UCB) — contains 120 mg pseudoephedrine hydrochloride (also 5 mg
cetirizine).
*
Claritin-D
Pseudoephedrine/loratadine (trade names Claritin-D, Clarinase, Clarinase Repetabs, Lorinase, Rhinos SR, Allerclear-D) is an orally administered combination drug used for the treatment of allergic rhinitis and the common cold. This drug can be bou ...
(made by
Bayer Healthcare
Bayer AG (, commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of business include pharmaceutica ...
) — contains 120 mg of pseudoephedrine sulfate (also 5 mg of
loratadine).
*
Claritin-D 24 Hour (made by
Bayer Healthcare
Bayer AG (, commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of business include pharmaceutica ...
) — contains 240 mg of pseudoephedrine sulfate (also 10 mg of
loratadine).
*
Codral (made by
Asia-Pacific
Asia-Pacific (APAC) is the part of the world near the western Pacific Ocean. The Asia-Pacific region varies in area depending on context, but it generally includes East Asia, Russian Far East, South Asia, Southeast Asia, Australia and Paci ...
subsidiary of
Johnson & Johnson
Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
) — Codral Original contains pseudoephedrine, Codral New Formula substitutes phenylephrine for pseudoephedrine.
*
Congestal (made by
SIGMA Pharmaceutical Industries) — contains 60 mg pseudoephedrine hydrochloride (also 650 mg
paracetamol and 4 mg
chlorpheniramine
Chlorphenamine (CP, CPM), also known as chlorpheniramine, is an antihistamine used to treat the symptoms of allergic conditions such as allergic rhinitis (hay fever). It is taken by mouth. The medication takes effect within two hours and lasts ...
).
*
Contac (made by
GlaxoSmithKline) — previously contained pseudoephedrine, now contains phenylephrine. As at Nov 2014 UK version still contains 30 mg pseudoephedrine hydrochloride per tablet.
*
Demazin (made by
Bayer Healthcare
Bayer AG (, commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of business include pharmaceutica ...
) — contains pseudoephedrine sulfate and chlorpheniramine maleate
*
Eltor (made by
Sanofi Aventis) — contains pseudoephedrine hydrochloride.
*
Mucinex D (made by
Reckitt Benckiser
Reckitt Benckiser Group plc, trading as Reckitt, is a British multinational consumer goods company headquartered in Slough, England. It is a producer of health, hygiene and nutrition products. The company was formed in March 1999 by the merge ...
) — contains 60 mg pseudoephedrine hydrochloride (also 1200 mg
guaifenesin).
*
Nexafed (made by
Acura Pharmaceuticals) — contains 30 mg pseudoephedrine per tablet, formulated with Impede Meth-Deterrent technology.
*
Nurofen
Nurofen is a brand name range of pain-relief medication containing ibuprofen made by the British multinational Reckitt. Introduced in 1983, the Nurofen brand was acquired following Reckitt Benckiser's acquisition of Boots in 2005. The brand is ...
Cold & Flu (made by
Reckitt Benckiser
Reckitt Benckiser Group plc, trading as Reckitt, is a British multinational consumer goods company headquartered in Slough, England. It is a producer of health, hygiene and nutrition products. The company was formed in March 1999 by the merge ...
) — contains 30 mg pseudoephedrine hydrochloride (also 200 mg
ibuprofen).
*Respidina – contains 120 mg of pseudoephedrine in the form of extended release tablets.
*
Rhinex Flash (made by
Pharma Product Manufacturing, Cambodia) — contains pseudoephedrine combined with
paracetamol and
triprolidine.
*
Rhinos SR (made by
Dexa Medica) — contains 120 mg of pseudoephedrine hydrochloride (also 5 mg loratadine).
*Rino-Ebastel (made by
Almirall) – contains 120 mg of pseudoephedrine hydrochloride (also 10 mg
ebastine).
*
Sinufed (made by
Trima) — contains 60 mg pseudoephedrine hydrochloride.
*
Sinutab (made by
McNeil Consumer Healthcare, a
Johnson & Johnson
Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
company) — contains 500 mg paracetamol and 30 mg pseudoephedrine hydrochloride.
*
Sudafed
Pseudoephedrine (PSE) is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It may be used as a nasal/sinus decongestant, as a stimulant, or as a wakefulness-promoting agent in higher doses.
It was first characte ...
Decongestant (made by
McNeil Consumer Healthcare, a
Johnson & Johnson
Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
company) — contains 60 mg of pseudoephedrine hydrochloride.
*
Theraflu
Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including a ...
(made by
Novartis
Novartis AG is a Swiss-American multinational pharmaceutical corporation based in Basel, Switzerland and
Cambridge, Massachusetts, United States (global research).name="novartis.com">https://www.novartis.com/research-development/research-lo ...
) — previously contained pseudoephedrine, now contains
phenylephrine.
*
Unifed (made by
United Pharmaceutical Manufacturer, Jordan) — contains pseudoephedrine hydrochloride (also
triprolidine and
guaifenesin).
*
Zyrtec-D 12 Hour (made by
McNeil Consumer Healthcare, a
Johnson & Johnson
Johnson & Johnson (J&J) is an American multinational corporation founded in 1886 that develops medical devices, pharmaceuticals, and consumer packaged goods. Its common stock is a component of the Dow Jones Industrial Average and the company i ...
company) — contains 120 mg pseudoephedrine hydrochloride (also 5 mg of
cetirizine).
*Zephrex-D (made by
Westport Pharmaceuticals) – a special meth-resistant form of pseudoephedrine that becomes gooey when heated
Legal status
Australia
Illicit diversion of pseudoephedrine in Australia has caused significant changes to the way the products are regulated. , all products containing pseudoephedrine have been rescheduled as either "Pharmacist Only Medicines" (Schedule 3) or "Prescription Only Medicines" (Schedule 4), depending on the amount of pseudoephedrine in the product. A Pharmacist Only Medicine may only be sold to the public if a pharmacist is directly involved in the transaction. These medicines must be kept behind the counter, away from public access.
Pharmacists are also encouraged (and in some states required) to log purchases with the online database Project STOP. This system aims to prevent individuals from purchasing small quantities of pseudoephedrine from many different pharmacies.
As a result, many pharmacies no longer stock Sudafed, the common brand of pseudoephedrine cold/sinus tablets, opting instead to sell Sudafed PE, a
phenylephrine product that has not been proven effective in clinical trials.
Canada
Health Canada has investigated the risks and benefits of pseudoephedrine and
ephedrine/
Ephedra. Near the end of the study, Health Canada issued a warning on their website stating that those who are under the age of 12, or who have heart disease and may have strokes, should avoid taking pseudoephedrine and ephedrine. Also, they warned that everyone should avoid taking ephedrine or pseudoephrine with other stimulants like
caffeine
Caffeine is a central nervous system (CNS) stimulant of the methylxanthine chemical classification, class. It is mainly recreational drug use, used recreationally as a Nootropic, cognitive enhancer, increasing alertness and attentional perfor ...
. They also banned all products that contain both ephedrine (or pseudoephedrine) and caffeine.
Products whose only medicinal ingredient is pseudoephedrine must be kept behind the pharmacy counter. Products containing pseudoephedrine along with other medicinal ingredients may be displayed on store shelves but may be sold only in a pharmacy when a pharmacist is present.
Colombia
The Colombian government prohibited the trade of pseudoephedrine in 2010.
Japan
Medications that contain more than 10% pseudoephedrine are prohibited under the Stimulants Control Law in Japan.
Mexico
On 23 November 2007, the use and trade of pseudoephedrine in Mexico was made illegal as it was argued that it was extremely popular as a precursor in the synthesis of methamphetamine.
Netherlands
Pseudoephedrine was withdrawn from sale in 1989 due to concerns about adverse cardiac side effects.
New Zealand
In New Zealand, pseudoephedrine is currently classified as a Class B Part II controlled drug in the
Misuse of Drugs Act 1975, making it illegal to supply or possess except on prescription.
Pseudoephedrine, ephedrine, and any product containing these substances, e.g. cold and flu medicines, were first classified in October 2004 as Class C Part III (partially exempted) controlled drugs, due to being the principal ingredient in methamphetamine. New Zealand Customs and police officers continued to make large interceptions of precursor substances believed to be destined for
methamphetamine production. On 9 October 2009, Prime Minister
John Key announced pseudoephedrine-based cold and flu tablets would become prescription-only drugs and reclassified as a class B2 drug. The law was amended by The Misuse of Drugs Amendment Bill 2010, which passed in August 2011.
Turkey
In
Turkey
Turkey ( tr, Türkiye ), officially the Republic of Türkiye ( tr, Türkiye Cumhuriyeti, links=no ), is a transcontinental country located mainly on the Anatolian Peninsula in Western Asia, with a small portion on the Balkan Peninsula ...
, medications containing pseudoephedrine are available with prescription only.
United Kingdom
In the UK, pseudoephedrine is available over the counter under the supervision of a qualified pharmacist, or on prescription. In 2007, the
MHRA reacted to concerns over diversion of ephedrine and pseudoephedrine for the illicit manufacture of methamphetamine by introducing voluntary restrictions limiting over the counter sales to one box containing no more than 720 mg of pseudoephedrine in total per transaction. These restrictions became law in April 2008. No form of ID is required.
United States
=Federal
=
The
United States Congress
The United States Congress is the legislature of the federal government of the United States. It is Bicameralism, bicameral, composed of a lower body, the United States House of Representatives, House of Representatives, and an upper body, ...
has recognized that pseudoephedrine is used in the illegal manufacture of methamphetamine. In 2005, the
Committee on Education and the Workforce heard testimony concerning education programs and state legislation designed to curb this illegal practice.
Attempts to control the sale of the drug date back to 1986, when federal officials at the
Drug Enforcement Administration
The Drug Enforcement Administration (DEA; ) is a United States federal law enforcement agency under the U.S. Department of Justice tasked with combating drug trafficking and distribution within the U.S. It is the lead agency for domestic en ...
(DEA) first drafted legislation, later proposed by Senator
Bob Dole, that would have placed a number of chemicals used in the manufacture of illicit drugs under the
Controlled Substances Act
The Controlled Substances Act (CSA) is the statute establishing federal U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United States ...
. The bill would have required each transaction involving pseudoephedrine to be reported to the government, and federal approval of all imports and exports. Fearing this would limit legitimate use of the drug, lobbyists from over the counter drug manufacturing associations sought to stop this legislation from moving forward, and were successful in exempting from the regulations all chemicals that had been turned into a legal final product, such as Sudafed.
Prior to the passage of the
Combat Methamphetamine Epidemic Act of 2005, sales of the drug became increasingly regulated, as DEA regulators and pharmaceutical companies continued to fight for their respective positions. The DEA continued to make greater progress in their attempts to control pseudoephedrine as methamphetamine production skyrocketed, becoming a serious problem in the western United States. When purity dropped, so did the number of people in rehab and people admitted to emergency rooms with methamphetamine in their systems. This reduction in purity was usually short lived, however, as methamphetamine producers eventually found a way around the new regulations.
Congress passed the ''
Combat Methamphetamine Epidemic Act of 2005'' ("CMEA") as an amendment to the renewal of the
USA Patriot Act
The USA PATRIOT Act (commonly known as the Patriot Act) was a landmark Act of the United States Congress, signed into law by President George W. Bush. The formal name of the statute is the Uniting and Strengthening America by Providing Appro ...
.
[ ] Signed into law by president
George W. Bush on March 6, 2006, the act amended , concerning the sale of pseudoephedrine-containing products. The law mandated two phases, the first needing to be implemented by April 8, 2006, and the second to be completed by September 30, 2006. The first phase dealt primarily with implementing the new buying restrictions based on amount, while the second phase encompassed the requirements of storage, employee training, and record keeping.
Though the law was mainly directed at pseudoephedrine products it also applies to all over-the-counter products containing ephedrine, pseudoephedrine, and phenylpropanolamine, their salts, optical isomers,
and salts of optical isomers.
Pseudoephedrine was defined as a "
scheduled listed chemical product" under (45(A)). The act included the following requirements for merchants ("regulated sellers") who sell such products:
* Required a retrievable record of all purchases, identifying the name and address of each party, to be kept for two years
* Required verification of proof of identity of all purchasers
* Required protection and disclosure methods in the collection of personal information
* Required reports to the
Attorney General
In most common law jurisdictions, the attorney general or attorney-general (sometimes abbreviated AG or Atty.-Gen) is the main legal advisor to the government. The plural is attorneys general.
In some jurisdictions, attorneys general also have exec ...
of any suspicious payments or disappearances of the regulated products
* Required training of employees with regard to the requirements of the CMEA. Retailers must self-certify as to training and compliance.
* The non-liquid dose form of regulated products may only be sold in unit dose blister packs
* Regulated products must be stored behind the counter or in a locked cabinet in such a way as to restrict public access
* Sales limits (per customer):
** Daily sales limit—must not exceed 3.6 grams of pseudoephedrine base without regard to the number of transactions
** 30-day (not monthly) sales limit—must not exceed 7.5 grams of pseudoephedrine base if sold by mail order or "mobile retail vendor"
** 30-day purchase limit—must not exceed 9 grams of pseudoephedrine base. (A misdemeanor possession offense under for the person who buys it.)
In regards to the identification that may be used by an individual buying pseudoephedrine products the following constitute acceptable forms of identification:
* US passport
* Alien registration or permanent resident card
* Unexpired foreign passport with temporary I-551 stamp
* Unexpired Employment Authorization Document
* Driver's License or Government issued identification card (including Canadian driver's license)
* School ID with picture
* Voter's Registration card
* US Military Card
* Native American tribal documents
The requirements were revised in the Methamphetamine Production Prevention Act of 2008 to require that a regulated seller of scheduled listed chemical products may not sell such a product unless the purchaser:
[ ]
* Presents a government issued photographic identification; and
* Signs the written logbook with their name, address, and time and date of the sale
=State
=
Most states also have laws regulating pseudoephedrine.
The states of Alabama, Arizona, Arkansas, California, Colorado, Delaware, Florida, Georgia, Hawaii () Idaho, Illinois, Indiana, Iowa, Kansas, Kentucky, Louisiana (), Massachusetts, Michigan, Minnesota, Mississippi, Missouri, Montana, Nebraska, Nevada, New Jersey, North Carolina, Ohio, Oklahoma, Oregon, Pennsylvania, South Dakota, Tennessee, Texas, Utah, Vermont, Virginia, Washington, West Virginia and Wisconsin have laws requiring pharmacies to sell pseudoephedrine "behind the counter". Though the drug can be purchased without a prescription, states can limit the number of units sold and can collect personal information from purchasers.
''
The states of Oregon and Mississippi previously required a prescription for the purchase of products containing pseudoephedrine. However as of January 1, 2022 these restrictions have been repealed The state of Oregon reduced the number of methamphetamine lab seizures from 467 in 2004 (the final full year before implementation of the prescription only law) to a new low of 12 in 2009.
The decrease in
meth lab
A rolling meth lab is a transportable laboratory that is used to illegally produce methamphetamine.Staff writerMethamphetamine, meth-lab assessment and clean-up" ''Forensic Applications Consulting Technologies Inc.'' Retrieved on 2009-02-14. Ro ...
incidents in Oregon occurred largely before the prescription-only law took effect, according to a NAMSDL report titled ''Pseudoephedrine Prescription Laws in Oregon and Mississippi''.
[ The report posits that the decline in meth lab incidents in both states may be due to other factors: "Mexican traffickers may have contributed to the decline in meth labs in Mississippi and Oregon (and surrounding states) as they were able to provide ample supply of equal or greater quality meth at competitive prices". Additionally, similar decreases in meth lab incidents were seen in surrounding states, according to the report, and meth-related deaths in Oregon have dramatically risen since 2007. Some municipalities in Missouri have enacted similar ordinances, including ]Washington
Washington commonly refers to:
* Washington (state), United States
* Washington, D.C., the capital of the United States
** A metonym for the federal government of the United States
** Washington metropolitan area, the metropolitan area centered o ...
, Union, New Haven
New Haven is a city in the U.S. state of Connecticut. It is located on New Haven Harbor on the northern shore of Long Island Sound in New Haven County, Connecticut and is part of the New York City metropolitan area. With a population of 134,023 ...
, Cape Girardeau and Ozark. Certain pharmacies in Terre Haute, Indiana do so as well.
Another approach to controlling the drug on the state level mandated by some state governments to control the purchases of their citizens is the use of electronic tracking systems, which require the electronic submission of specified purchaser information by all retailers who sell pseudoephedrine. Thirty-two states now require the National Precursor Log Exchange (NPLEx) to be used for every pseudoephedrine and ephedrine OTC purchase, and ten of the eleven largest pharmacy chains in the US voluntarily contribute all of their similar transactions to NPLEx. These states have seen dramatic results in reducing the number of methamphetamine laboratory seizures. Prior to implementation of the system in Tennessee in 2005, methamphetamine laboratory seizures totaled 1,497 in 2004, but were reduced to 955 in 2005, and 589 in 2009. Kentucky's program was implemented statewide in 2008, and since statewide implementation, the number of laboratory seizures has significantly decreased. Oklahoma initially experienced success with their tracking system after implementation in 2006, as the number of seizures dropped in that year and again in 2007. In 2008, however, seizures began rising again, and have continued to rise in 2009. Nonetheless, when Oklahoma adopted NPLEx, their lab seizures also dropped significantly.
NPLEx appears to be successful by requiring the real-time submission of transactions, thereby enabling the relevant laws to be enforced at the point of sale. By creating a multi-state database and the ability to compare all transactions quickly, NPLEx enables pharmacies to deny purchases that would be illegal based on gram limits, age, or even to convicted meth offenders in some states. NPLEx also enforces the federal gram limits across state lines, which was impossible with state-operated systems. Access to the records is by law enforcement agencies only, through an online secure portal.
In popular culture
In the pilot episode of ''Breaking Bad'', Walter White first synthesizes methamphetamine through the Nagai route, using red phosphorus
Elemental phosphorus can exist in several allotropes, the most common of which are white and red solids. Solid violet and black allotropes are also known. Gaseous phosphorus exists as diphosphorus and atomic phosphorus.
White phosphorus
Whit ...
and iodine to reduce pseudoephedrine.
In the episode "Vitamin D
Vitamin D is a group of Lipophilicity, fat-soluble secosteroids responsible for increasing intestinal absorption of calcium, magnesium, and phosphate, and many other biological effects. In humans, the most important compounds in this group ar ...
" of '' Glee'', Terri
Terri is an alternative spelling of Terry. It is a common feminine given name and is also a diminutive for Teresa.
Notable people with the name include:
*Terri Allard (born 1962), American country/folk singer/songwriter
*Terri S. Armstrong, Amer ...
takes a job as the school nurse to stop her husband, Will Schuester, from becoming closer to guidance counsellor Emma Pillsbury ( Jayma Mays), but is fired after giving the students performance-enhancing pseudoephedrine tablets.
In her 2013 single "Avant Gardener
''The Double EP: A Sea of Split Peas'' is an EP by Australian rock musician Courtney Barnett which compiles two of her previous EPs: ''I've Got a Friend Called Emily Ferris'' (tracks 7-12) and ''How to Carve a Carrot into a Rose'' (tracks 1-6.) It ...
", Australian rock musician Courtney Barnett
Courtney Melba Barnett (born 3 November 1987) is an Australian singer, songwriter, and musician. Known for her deadpan singing style and witty, rambling lyrics, she attracted attention with the release of her debut EP ''I've Got a Friend Calle ...
refers to the effects of pseudoephedrine: "Reminds me of the time / When I was really sick and I / Had too much pseudoephedrine and I / Couldn't sleep at night".
In her 2017 album '' Melodrama'', pop artist Lorde references pseudoephedrine on the song "Writer in the Dark
"Writer in the Dark" is a song recorded by New Zealand singer-songwriter Lorde for her second album ''Melodrama'' (2017). She co-wrote and co-produced the track with Jack Antonoff. It is a piano ballad with sparse production and an outro. Its ...
". The lyric reads: "I still feel you, now and then / Slow like pseudoephedrine / When you see me, will you say I've changed?"
Synthesis
Although pseudoephedrine occurs naturally as an alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of simila ...
in certain plant species (for example, as a constituent of extracts from the '' Ephedra'' species, also known as ''ma huang'', in which it occurs together with other isomers of ephedrine), the majority of pseudoephedrine produced for commercial use is derived from yeast
Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constit ...
fermentation of dextrose in the presence of benzaldehyde. In this process, specialized strains of yeast (typically a variety of '' Candida utilis'' or ''Saccharomyces cerevisiae
''Saccharomyces cerevisiae'' () (brewer's yeast or baker's yeast) is a species of yeast (single-celled fungus microorganisms). The species has been instrumental in winemaking, baking, and brewing since ancient times. It is believed to have b ...
'') are added to large vats containing water, dextrose and the enzyme pyruvate decarboxylase (such as found in beets and other plants). After the yeast has begun fermenting the dextrose, the benzaldehyde is added to the vats, and in this environment the yeast converts the ingredients to the precursor l-phenylacetylcarbinol (L-PAC). L-PAC is then chemically converted to pseudoephedrine via reductive amination.
The bulk of pseudoephedrine is produced by commercial pharmaceutical manufacturers in India
India, officially the Republic of India (Hindi: ), is a country in South Asia. It is the List of countries and dependencies by area, seventh-largest country by area, the List of countries and dependencies by population, second-most populous ...
and China
China, officially the People's Republic of China (PRC), is a country in East Asia. It is the world's List of countries and dependencies by population, most populous country, with a Population of China, population exceeding 1.4 billion, slig ...
, where economic and industrial conditions favor its mass production for export.[Suo, Steve. Clamp down on shipments of raw ingredients. The Oregonian; 6 October 2004. From a version reprinted on a U.S]
congressional caucus
website.
See also
* Amphetamine
* Carbinoxamine/pseudoephedrine
* Ephedrine
* Methamphetamine
* ''N''-Methylpseudoephedrine
* Phenylephrine
* Phenylpropanolamine
Phenylpropanolamine (PPA) is a sympathomimetic agent which is used as a decongestant and appetite suppressant. It was commonly used in prescription and over-the-counter cough and cold preparations. In veterinary medicine, it is used to cont ...
* Thomas Latham, sponsor of the "Angie Fatino Save the Children from Meth Act"
References
External links
*
{{Portal bar , Medicine
Amphetamine alkaloids
Decongestants
Methamphetamine
Norepinephrine releasing agents
Phenylethanolamines