Methamphetamine - Department of Electrical Engineering

Transcription

Methamphetamine
1
Methamphetamine
Methamphetamine
Systematic (IUPAC) name
N-methyl-1-phenylpropan-2-amine
Identifiers
[1]
CAS number
537-46-2
ATC code
N06 BA03
PubChem
CID 1206
DrugBank
DB01577
ChemSpider
1169
UNII
44RAL3456C
KEGG
D08187
ChEMBL
CHEMBL1201201
[2]
[3]
[4]
[5]
[6]
[7]
[8]
Methamphetamine
2
Synonyms
Desoxyephedrine
Pervitin
Anadrex
Methedrine
Methylamphetamine
Syndrox
Desoxyn
Chemical data
Formula
C10H15N
Mol. mass
149.233 g/mol
SMILES
eMolecules
[9]
& PubChem
[10]
Pharmacokinetic data
Bioavailability
62.7% oral; 79% nasal; 90.3% smoked; 99% rectally; 100% IV
Metabolism
Hepatic
Half-life
9–12 hours
Excretion
Renal
[11]
Therapeutic considerations
Pregnancy cat. C(US)
Legal status
Controlled (S8) (AU) Schedule I (CA) Schedule II (US) Class
A(NZ)
Schedule 5(SA)
Injectable:Class A, Oral: A(UK)
Routes
Medical: Oral
Recreational: Oral, I.V., I.M., Insufflation, Inhalation, Rectal
(what is this?) (verify)
[12]
Methamphetamine (pronounced /ˌmɛθæmˈfɛtəmiːn/ listen [13]), also known as metamfetamine (INN for the (+)
form), methylamphetamine, N-methylamphetamine, desoxyephedrine, and colloquially as "meth" or "crystal
meth", is a psychostimulant of the phenethylamine and amphetamine class of drugs. It increases alertness,
concentration, energy, and in high doses, can induce euphoria, enhance self-esteem, and increase libido.[14] [15]
Methamphetamine has high potential for abuse and addiction by activating the psychological reward system via
triggering a cascading release of dopamine, norepinephrine and serotonin in the brain. Methamphetamine is FDA
approved for the treatment of ADHD and exogenous obesity, marketed in the USA under the trademark name
Desoxyn.[16]
Methamphetamine is illicitly synthesized and then sold in a crystalline form resembling small shards of odorless,
bitter-tasting crystals; leading to the colloquial nickname "crystal meth". Following a period of heavy use, also
known as "bingeing", which typically lasts days or even weeks, a severe withdrawal syndrome lasting up to ten days
can occur, primarily consisting of depression, fatigue, excessive sleeping and an increased appetite. Chronic
methamphetamine abuse may result in prolonged psychiatric disorders, cognitive impairment, as well as an increased
risk of developing Parkinson's disease.
As a result of methamphetamine-induced neurotoxicity to dopaminergic neurons, chronic abuse may also lead to
symptoms which persist beyond the withdrawal period for months, and even up to a year.[17] Research has found that
20% of methamphetamine addicts experience a psychosis resembling schizophrenia which persists for longer than
six months post-methamphetamine use; this amphetamine psychosis can be resistant to traditional treatment.[18] In
addition to psychological harm, physical harm, primarily consisting of cardiovascular damage, may occur with
Methamphetamine
chronic abuse or acute overdose.[19]
History
Methamphetamine was first synthesized from ephedrine in Japan in
1893 by chemist Nagai Nagayoshi.[20] The term "methamphetamine"
was derived from elements of the chemical structure of this new
compound: methyl alpha-methylphenylethylamine. In 1919,
crystallized methamphetamine was synthesized by Akira Ogata via
reduction of ephedrine using red phosphorus and iodine. In 1943,
Abbott Laboratories requested for its approval from the U.S. Food and
Drug Administration (FDA) for the treatment of narcolepsy, mild
depression, postencephalitic parkinsonism, chronic alcoholism,
cerebral arteriosclerosis, and hay fever. Methamphetamine was
approved for all of these indications in December, 1944. All of these
indication
approvals were eventually removed. The only two approved
Crystal methamphetamine was first synthesized
marketing indications remaining for methamphetamine are for
in 1919 by Akira Ogata.
attention-deficit hyperactivity disorder (ADHD) and the short-term
management of exogenous obesity, although the drug is clinically established as effective in the treatment of
narcolepsy.[21]
World War II
One of the earliest uses of methamphetamine was during World War II, when it was used by Axis and Allied
forces.[22] The German military dispensed it under the trademark name Pervitin. It was widely distributed across
rank and division, from elite forces to tank crews and aircraft personnel, with many millions of tablets being
distributed throughout the war.[23] From 1942 until his death in 1945, Adolf Hitler may have been given intravenous
injections of methamphetamine by his personal physician Theodor Morell. It is possible that it was used to treat
Hitler's speculated Parkinson's disease, or that his Parkinson-like symptoms that developed from 1940 onwards
resulted from using methamphetamine.[24] In Japan, methamphetamine was sold under the registered trademark of
Philopon (ヒロポン hiropon) by Dainippon Sumitomo Pharma for civilian and military use. As with the rest of the
world at the time, the side effects of methamphetamine were not well studied, and regulation was not seen as
necessary.
Post-war usage
After World War II, a large Japanese military stockpile of methamphetamine, known by its trademark Philopon,
flooded the market.[25] The Japanese Ministry of Health banned it in 1951; since then, it has been increasingly
produced by the Yakuza criminal organization.[26] On the streets, it is also known as S, Shabu, and Speed, in
addition to its old trademarked name. In the 1950s, there was a rise in the legal prescription of methamphetamine to
the American public. In the 1954 edition of Pharmacology and Therapeutics, indications for methamphetamine
included "narcolepsy, postencephalitic parkinsonism, alcoholism, certain depressive states, and in the treatment of
obesity."[27] The 1960s saw the start of significant use of clandestinely manufactured methamphetamine, as well as
methamphetamine created in users' own homes for personal and recreational use which continues to this day.
3
Methamphetamine
Legal restrictions
In 1983, laws were passed in the United States
prohibiting possession of precursors and equipment for
methamphetamine production. This was followed a
month later by a bill passed in Canada enacting similar
laws. In 1986, the U.S. government passed the Federal
Controlled Substance Analogue Enforcement Act in an
attempt to curb the growing use of designer drugs.
Despite this, use of methamphetamine expanded
throughout rural United States, especially through the
Midwest and South.[28]
Since 1989, five U.S. federal laws and dozens of state
laws have been imposed in an attempt to curb the
Waste left over from an illicit meth lab.
production of methamphetamine. Methamphetamine
can be produced in home laboratories using
pseudoephedrine or ephedrine, which, at the time, were the active ingredients in over-the-counter drugs such as
Sudafed and Contac. Preventive legal strategies of the past 17 years have steadily increased restrictions to the
distribution of pseudoephedrine/ephedrine-containing products.[29]
As a result of the U.S. Combat Methamphetamine Epidemic Act of 2005, a subsection of the USA PATRIOT Act,
there are restrictions on the amount of pseudoephedrine and ephedrine one may purchase in a specified time period
and further requirements that these products must be stored in order to prevent theft.[29] Increasingly strict
restrictions have resulted in the reformulation of many over-the-counter drugs, and some, such as Actifed, have been
discontinued entirely in the United States.
Meth lab waste is extremely hazardous and toxic. Waste cleanup is a major issue for authorities and property owners.
Common wastes include brake cleaner, ammonia, soda bottles, kitty litter, lithium batteries, engine starter, matches,
and pseudoephedrine blister packs.[30]
Pharmacology
A member of the family of phenethylamines, methamphetamine is chiral, with two isomers, levorotary and
dextrorotatory.[11] The levorotary form, called levomethamphetamine, is an over-the-counter drug used in inhalers
for nasal decongestion. Levomethamphetamine does not possess any significant central nervous system activity or
addictive properties. This article deals only with the dextrorotatory form, called dextromethamphetamine, and the
racemic form.
Methamphetamine is a potent central nervous system stimulant that affects neurochemical mechanisms responsible
for regulating heart rate, body temperature, blood pressure, appetite, attention, mood and emotional responses
associated with alertness or alarming conditions.[11] The acute physical effects of the drug closely resemble the
physiological and psychological effects of an epinephrine-provoked fight-or-flight response, including increased
heart rate and blood pressure, vasoconstriction (constriction of the arterial walls), bronchodilation, and
hyperglycemia (increased blood sugar). Users experience an increase in focus, increased mental alertness, and the
elimination of fatigue, as well as a decrease in appetite.
The methyl group is responsible for the potentiation of effects as compared to the related compound amphetamine,
rendering the substance on the one hand more lipid-soluble, enhancing transport across the blood-brain barrier, and
on the other hand more stable against enzymatic degradation by monoamine oxidase (MAO). Methamphetamine
causes the norepinephrine, dopamine, and serotonin (5HT) transporters to reverse their direction of flow. This
inversion leads to a release of these transmitters from the vesicles to the cytoplasm and from the cytoplasm to the
4
Methamphetamine
synapse (releasing monoamines in rats with ratios of about NE:DA = 1:2, NE:5HT= 1:60), causing increased
stimulation of post-synaptic receptors. Methamphetamine also indirectly prevents the reuptake of these
neurotransmitters, causing them to remain in the synaptic cleft for a prolonged period (inhibiting monoamine
reuptake in rats with ratios of about: NE:DA = 1:2.35, NE:5HT = 1:44.5).[31]
Methamphetamine is a potent neurotoxin, shown to
cause dopaminergic degeneration.[32] [33] High doses of
methamphetamine produce losses in several markers of
brain dopamine and serotonin neurons. Dopamine and
serotonin concentrations, dopamine and 5HT uptake
sites, and tyrosine and tryptophan hydroxylase
activities are reduced after the administration of
methamphetamine. It has been proposed that dopamine
plays
a
role
in
methamphetamine-induced
neurotoxicity, because experiments that reduce
Ball-and-stick model of methamphetamine
dopamine production or block the release of dopamine
decrease the toxic effects of methamphetamine
administration. When dopamine breaks down, it produces reactive oxygen species such as hydrogen peroxide.
It is likely that the approximate twelvefold increase in dopamine levels and subsequent oxidative stress that occurs
after taking methamphetamine mediates its neurotoxicity.[34]
Recent research published in the Journal of Pharmacology And Experimental Therapeutics (2007)[35] indicates that
methamphetamine binds to and activates a G protein-coupled receptor called TAAR1.[36] TAARs are a newly
discovered receptor family[37] [38] whose members are activated by a number of amphetamine-like molecules[38]
called trace amines, thyronamines,[39] and certain volatile odorants.[40]
It has been demonstrated that a high ambient temperature increases the neurotoxic effects of methamphetamine.[41]
Effects
Physical effects
Physical effects can include anorexia, hyperactivity, dilated pupils, flushing, restlessness, dry mouth, headache,
tachycardia, bradycardia, tachypnea, hypertension, hypotension, hyperthermia, diaphoresis, diarrhea, constipation,
blurred vision, dizziness, twitching, insomnia, numbness, palpitations, arrhythmias,[42] tremors, dry and/or itchy
skin, acne, pallor, and with chronic and/or high doses, convulsions,[43] heart attack,[44] stroke,[45] and death.[45] [46]
[47] [48] [49] [50]
Psychological effects
Psychological effects can include euphoria, anxiety, increased libido, alertness, concentration, energy, self-esteem,
self-confidence, sociability, irritability, aggression, psychosomatic disorders, psychomotor agitation, grandiosity,
hallucinations, excessive feelings of power and invincibility, repetitive and obsessive behaviors, paranoia, and with
chronic and/or high doses, amphetamine psychosis can occur.[45] [51]
Withdrawal effects
Withdrawal symptoms of methamphetamine primarily consist of fatigue, depression and an increased appetite.
Symptoms may last for days with occasional use and weeks or months with chronic use, with severity dependent on
the length of time and the amount of methamphetamine used. Withdrawal symptoms may also include anxiety,
agitation, akathisia, excessive sleeping, vivid or lucid dreams, deep REM sleep and suicidal ideation.[52]
5
Methamphetamine
Long-term effects
Methamphetamine use has a high association with depression and suicide as well as serious heart disease,
amphetamine psychosis, anxiety and violent behaviours. Methamphetamine also has a very high addiction risk.[19]
Methamphetamine is neurotoxic and is associated with an increased risk of Parkinson's disease.[17] [53]
Methamphetamine abuse can cause neurotoxicity which is believed to be responsible for causing persisting cognitive
deficits, such as memory, impaired attention and executive function. Over 20 percent of people addicted to
methamphetamine develop a long-lasting psychosis resembling schizophrenia after stopping methamphetamine
which persists for longer than 6 months and is often treatment resistant.[18]
Pharmacokinetics
Following oral administration, methamphetamine is readily absorbed with peak methamphetamine concentrations
occurring in 3.13 to 6.3 hours post ingestion. The amphetamine metabolite peaks at 10 to 24 hours.[11]
Methamphetamine is also well absorbed following inhalation and following intranasal administration.[11] It is
distributed to most parts of the body. Because methamphetamine has a high lipophilicity it is distributed across the
blood brain barrier and crosses the placenta.[11]
Methamphetamine is metabolized in the liver with the main metabolites being amphetamine (active) and
4-hydroxymethamphetamine; other minor metabolites include 4-hydroxyamphetamine, norephedrine, and
4-hydroxynorephedrine.[11] [54] [55] Other drugs metabolized to amphetamine and methamphetamine include
benzphetamine, furfenorex, and famprofazone.[56] [57] Selegiline (marketed as Deprenyl, EMSAM, and others) is
metabolized into the less active L-isomer of amphetamine and the inactive L-isomer of methamphetamine.[11]
Although only the D-Isomer of selegiline will metabolize into active metabolites, both isomers may cause a positive
result for methamphetamine and amphetamine on a drug test, in certain cases.[58]
It is excreted by the kidneys, with the rate of excretion into the urine heavily influenced by urinary pH. Between
30-54% of an oral dose is excreted in urine as unchanged methamphetamine and 10-23% as unchanged
amphetamine. Following an intravenous dose, 45% is excreted as unchanged parent drug and 7% amphetamine.[59]
The half-life of methamphetamine is variable with a mean value of between 9 and 12 hours.[11]
Detection in biological fluids
Methamphetamine and amphetamine are often measured in urine, sweat or saliva as part of a drug-abuse testing
program, in plasma or serum to confirm a diagnosis of poisoning in hospitalized victims, or in whole blood to assist
in a forensic investigation of a traffic or other criminal violation or a case of sudden death. Chiral techniques may be
employed to help distinguish the source of the drug, whether obtained legally (via prescription) or illicitly, or
possibly as a result of formation from a prodrug such as famprofazone or selegiline. Chiral separation is needed to
assess the possible contribution of l-methamphetamine (Vicks Inhaler) toward a positive test result.[60] [61] [62]
Tolerance
As with other amphetamines, tolerance to methamphetamine is not completely understood but known to be
sufficiently complex that it cannot be explained by any single mechanism. The extent of tolerance and the rate at
which it develops vary widely between individuals, and, even within one person, it is highly dependent on dosage,
duration of use, and frequency of administration. Tolerance to the awakening effect of amphetamines does not
readily develop, making them suitable for the treatment of narcolepsy.[63]
Short-term tolerance can be caused by depleted levels of neurotransmitters within the synaptic vesicles available for
release into the synaptic cleft following subsequent reuse (tachyphylaxis). Short-term tolerance typically lasts until
neurotransmitter levels are fully replenished; because of the toxic effects on dopaminergic neurons, this can be
greater than 2–3 days. Prolonged overstimulation of dopamine receptors caused by methamphetamine may
6
Methamphetamine
eventually cause the receptors to downregulate in order to compensate for increased levels of dopamine within the
synaptic cleft.[64] To compensate, larger quantities of the drug are needed in order to achieve the same level of
effects.
Reverse tolerance or sensitization can also occur.[63] The effect is well established, but the mechanism is not well
understood.
Addiction
Methamphetamine is very addictive.[65] While the withdrawal itself may not be dangerous, withdrawal symptoms are
common with heavy use and relapse is common.
Methamphetamine-induced hyperstimulation of pleasure pathways leads to anhedonia. It is possible that daily
administration of the amino acids L-tyrosine and L-5HTP/tryptophan can aid in the recovery process by making it
easier for the body to reverse the depletion of dopamine, norepinephrine, and serotonin. Although studies involving
the use of these amino acids have shown some success, this method of recovery has not been shown to be
consistently effective.
It is shown that taking ascorbic acid prior to using methamphetamine may help reduce acute toxicity to the brain, as
rats given the human equivalent of 5–10 grams of ascorbic acid 30 minutes prior to methamphetamine dosage had
toxicity mediated,[66] [67] yet this will likely be of little avail in solving the other serious behavioral problems
associated with methamphetamine use and addiction that many users experience. Large doses of ascorbic acid also
lower urinary pH, reducing methamphetamine's elimination half-life and thus decreasing the duration of its
actions.[68]
To combat addiction, doctors are beginning to use other forms of stimulants such as dextroamphetamine, the
dextrorotatory (right-handed) isomer of the amphetamine molecule, to break the addiction cycle in a method similar
to the use of methadone in the treatment of heroin addicts. There are no publicly available drugs comparable to
naloxone, which blocks opiate receptors and is therefore used in treating opiate dependence, for use with
methamphetamine problems.[69] However, experiments with some monoamine reuptake inhibitors such as
indatraline have been successful in blocking the action of methamphetamine.[70] There are studies indicating that
fluoxetine, bupropion and imipramine may reduce craving and improve adherence to treatment.[71] Research has also
suggested that modafinil can help addicts quit methamphetamine use.[72] [73]
Methamphetamine addiction is one of the most difficult forms of addictions to treat. Bupropion, aripiprazole, and
baclofen have been employed to treat post-withdrawal cravings, although the success rate is low. Modafinil is
somewhat more successful, but this is a Class IV scheduled drug. Ibogaine has been used with success in Europe,
where it is a Class I drug and available only for scientific research. Mirtazapine has been reported useful in some
small-population studies.[74]
As the phenethylamine phentermine is a constitutional isomer of methamphetamine, it has been suggested that it may
be effective in treating methamphetamine addiction. Phentermine is a central nervous system stimulant that acts on
dopamine and norepinephrine. When comparing (+)-Amphetamine, (+/-)-ephedrine, and phentermine, one key
difference among the three drugs is their selectivity for norepinephrine (NE) release vs. dopamine (DA) release. The
NE/DA selectivity ratios for these drugs as determined in vitro [(EC(50) NE(-1))/(EC(50) DA(-1))] are
(+/-)-ephedrine (18.6) > phentermine (6.7) > (+)-amphetamine (3.5).[75]
Abrupt interruption of chronic methamphetamine use results in the withdrawal syndrome in almost 90% of the cases.
The mental depression associated with methamphetamine withdrawal lasts longer and is more severe than that of
cocaine withdrawal.[71]
7
Methamphetamine
Medical use
Methamphetamine has been FDA approved for use in children and adults
under the trade name Desoxyn for the treatment of ADHD and exogenous
obesity, as well as off-label for the treatment of narcolepsy and
treatment-resistant depression.[21] Methamphetamine is known to produce
central effects similar to the other stimulants, but at smaller doses, with
fewer peripheral effects.[76] Methamphetamine's fat solubility also allows it
to enter the brain faster than other stimulants, where it is more stable
against degradation by monoamine oxidase (MAO).
Investigational use
A 2006 study by a group of University of Montana scientists showed that
Desoxyn 10 mg tablets (US)
methamphetamine appears to lessen damage to the brains of rats and gerbils
that have suffered strokes. Their preliminary research has found that small
amounts of methamphetamine created a protective effect, while higher doses increased damage. The findings have
shown that methamphetamine could be used medically to lessen stroke damage.[77]
Health issues
Meth mouth
Methamphetamine users and addicts may lose their teeth abnormally quickly, a condition informally known as meth
mouth. According to the American Dental Association, meth mouth "is probably caused by a combination of
drug-induced psychological and physiological changes resulting in xerostomia (dry mouth), extended periods of poor
oral hygiene, frequent consumption of high-calorie, carbonated beverages and bruxism (teeth grinding and
clenching). Some reports have also speculated that the caustic nature of the drug is a contributing factor.[78] [79]
Similar, though far less severe, symptoms have been reported in clinical use of regular amphetamine, where effects
are not exacerbated by extended periods of poor oral hygiene.[80] [81]
Public health issues
Short-term exposure to high concentrations of chemical vapors that may exist in methamphetamine laboratories can
cause severe health problems or even result in death. Exposure to these substances can occur from volatile air
emissions, spills, fires, and explosions.[82] Methamphetamine labs are often discovered when fire fighters respond to
a blaze. Methamphetamine cooks, their families, and first responders are at highest risk of acute health effects from
chemical exposure, including lung damage and chemical burns to the body. Following a seizure of a
methamphetamine lab, there is often a low exposure risk to chemical residues, however this contamination should be
sanitized. Chemical residues and lab wastes that are left behind at a former methamphetamine lab can result in health
problems for people who use the property, therefore local health departments should thoroughly assess the property
for hazards prior to allowing it to be reinhabited, especially by children.[83]
Use in pregnancy and breastfeeding
Methamphetamine passes through the placenta and is secreted into breast milk. Infants born to
methamphetamine-abusing mothers were found to have a significantly smaller gestational age-adjusted head
circumference and birth weight measurements. Methamphetamine exposure was also associated with neonatal
withdrawal symptoms of agitation, vomiting and tachypnea.[84] This withdrawal syndrome is relatively mild and
only requires medical intervention in approximately 4% of cases.[71]
8
Methamphetamine
Increased risk of sexually transmitted disease
Men who use methamphetamine, cocaine, MDMA, and ketamine are twice as likely to have unprotected sex,
according to British research.[85] American psychologist Perry N. Halkitis performed an analysis using data collected
from community-based participants among gay and bisexual men to examine the associations between
methamphetamine use and sexual risk taking behaviors. Methamphetamine use was found to be related to higher
frequencies of unprotected sexual intercourse in both HIV-positive and unknown casual partners. The association
between methamphetamine use and unprotected acts were also more pronounced in HIV-positive participants. These
findings suggested that methamphetamine use and engagement in unprotected anal intercourse are co-occurring risk
behaviors that potentially heighten the risk of HIV transmission among gay and bisexual men.[86] Methamphetamine
allows users to engage in prolonged sexual activity, which may cause genital sores and abrasions. Methamphetamine
can also cause sores and abrasions in the mouth via bruxism (teeth clenching and grinding), which can turn typically
low-risk sex acts, such as oral sex, into high-risk sexual activity.[87] As with the injection of any drug, if a group of
users share a common needle without sterilization procedures, blood-borne diseases, such as HIV or hepatitis, can be
transmitted. The level of needle sharing among methamphetamine users is similar to that among other drug injection
users.[88]
Routes of administration
Studies have shown that the subjective pleasure of drug use (the reinforcing component of addiction) is proportional
to the rate at which the blood level of the drug increases. These findings suggest the route of administration affects
the potential risk for psychological addiction independently of other risk factors, such as dosage and frequency of
use.[89] Intravenous injection is the fastest route of drug administration, causing blood concentrations to rise the most
quickly, followed by smoking, suppository (anal or vaginal insertion), insufflation (snorting), and ingestion
(swallowing). Ingestion does not produce a rush, an acute transcendent state of euphoria, as forerunner to the high
experienced with the use of methamphetamine, which is most pronounced with intravenous use. While the onset of
the rush induced by injection can occur in as little as a few seconds, the oral route of administration requires
approximately half an hour before the high sets in.[90]
Injection
Injection, also known as "slamming", "banging", "shooting up" or "mainlining", is a popular method used by addicts
which carries relatively greater risks than other methods of administration. The hydrochloride salt of
methamphetamine is soluble in water. Intravenous users may use any dose range, from less than 100 milligrams to
over one gram, using a hypodermic needle, although it should be noted that typically street methamphetamine is
"cut" with a water-soluble cutting material, which constitutes a significant portion of a given street
methamphetamine dose.[91] Intravenous users risk developing pulmonary embolism (PE), a blockage of the main
artery of the lung or one of its branches, and commonly develop skin rashes (also known as "speed bumps") or
infections at the site of injection. As with the injection of any drug, if a group of users share a common needle
without sterilization procedures, blood-borne diseases, such as HIV or hepatitis, can be transmitted.
Smoking
Smoking amphetamines refers to vaporizing it to inhale the resulting fumes, not burning it to inhale the resulting
smoke. It is commonly smoked in glass pipes made from glassblown Pyrex tubes and light bulbs. It can also be
smoked off aluminium foil, which is heated underneath by a flame. This method is also known as "chasing the white
dragon" (whereas smoking heroin is known as "chasing the dragon").[92] [93] There is little evidence that
methamphetamine inhalation results in greater toxicity than any other route of administration.[94] [95] Lung damage
has been reported with long-term use, but manifests in forms independent of route (pulmonary hypertension (PH)),
or limited to injection users (pulmonary embolism (PE)).
9
Methamphetamine
10
Insufflation
Another popular route to intake methamphetamine is insufflation (snorting), where a user crushes the
methamphetamine into a fine powder and then sharply inhales it (sometimes with a straw or a rolled up banknote, as
with cocaine) into the nose where methamphetamine is absorbed through the soft tissue in the mucous membrane of
the sinus cavity and straight into the bloodstream. Insufflation of methamphetamine can cause chemical damage to
teeth, as it draws methamphetamine down the nasal passage, draining in the back of the throat and saturating the
teeth with the caustic substances used in its illicit production.[79]
Suppository
Suppository (anal or vaginal insertion) is a less popular method of administration used in the community with
comparatively little research into its effects.[96] Information on its use is largely anecdotal with reports of increased
sexual pleasure and the effects of the drug lasting longer.[97] As methamphetamine is centrally active in the brain,
these effects are likely experienced through the higher bioavailability of the drug in the bloodstream (second to
injection) and the faster onset of action (than insufflation).[98] Nicknames for this method of use within
methamphetamine communities include a "butt rocket", a "booty bump", "potato thumping", "turkey basting",
"plugging", "boofing", "suitcasing", "keistering", "shafting", "bumming", and "shelving" (vaginal).[96] [99]
Illicit production
Synthesis
Crystal methamphetamine
Synthesis is relatively simple, but entails risk with
flammable and corrosive chemicals, particularly the
solvents used in extraction and purification; therefore,
illicit production is often discovered by fires and
explosions caused by the improper handling of volatile
or flammable solvents. Most of the necessary chemicals
are readily available in household products or
over-the-counter cold or allergy medicines. When
illicitly produced, methamphetamine is commonly
made by the reduction of ephedrine or
pseudoephedrine. The maximum conversion rate for
ephedrine and pseudoephedrine is 92%, although
typically, illicit methamphetamine laboratories convert
at a rate of 50% to 75%.[100]
Most methods of illicit production involve protonation of the hydroxyl group on the ephedrine or pseudoephedrine
molecule. Methamphetamine is most structurally similar to methcathinone and amphetamine. The most common
method for small-scale methamphetamine labs in the United States is primarily called the "Red, White, and Blue
Process", which involves red phosphorus, pseudoephedrine or ephedrine (white), and iodine (which is technically a
purple color in elemental form), from which hydroiodic acid is formed. In Australia, criminal groups have been
known to substitute "red" phosphorus with either hypophosphorous acid or phosphorous acid.[101] This is a
hazardous process for amateur chemists, because phosphine gas, a side-product from in situ hydroiodic acid
production, is extremely toxic to inhale.
Another common method uses the Birch reduction (also called the "Nagai method"),[102] in which metallic lithium,
commonly extracted from non-rechargeable lithium batteries, is substituted for difficult-to-find metallic sodium.
However, the Birch reduction is dangerous because the alkali metal and liquid anhydrous ammonia are both
Methamphetamine
11
extremely reactive, and the temperature of liquid ammonia makes it susceptible to explosive boiling when reactants
are added.
A completely different procedure of synthesis uses the
reductive
amination
of
phenylacetone
with
[104]
methylamine,
both of which are currently DEA list
I chemicals (as are pseudoephedrine and ephedrine).
The reaction requires a catalyst that acts as a reducing
agent, such as mercury-aluminum amalgam or platinum
dioxide, also known as Adams' catalyst. This was once
the preferred method of production by motorcycle
gangs in California,[105] until DEA restrictions on the
chemicals made the process difficult. Other less
common methods use other means of hydrogenation,
such as hydrogen gas in the presence of a catalyst.
Anti-meth sign on tank of anhydrous ammonia (Otley, Iowa).
Methamphetamine labs can give off noxious fumes,
Anhydrous ammonia is a common farm fertilizer which is also a
critical ingredient in making methamphetamine. In 2005, the state of
such as phosphine gas, methylamine gas, solvent
Iowa gave out thousands of locks in order to prevent criminals from
vapors, acetone or chloroform, iodine vapors, white
[103]
accessing the tanks.
phosphorus,
anhydrous
ammonia,
hydrogen
chloride/muriatic
acid,
hydrogen
iodide,
lithium/sodium metal, ether, or methamphetamine vapors. If performed by amateurs, manufacturing
methamphetamine can be extremely dangerous. If the red phosphorus overheats, because of a lack of ventilation,
phosphine gas can be produced. This gas is highly toxic and, if present in large quantities, is likely to explode upon
autoignition from diphosphine, which is formed by overheating phosphorus.
In recent years, reports of a simplified "Shake 'n Bake" synthesis have surfaced. The method is suitable for such
small batches that pseudoephedrine restrictions are less effective, it uses chemicals that are easier to obtain (though
no less dangerous than traditional methods), and it is so easy to carry out that some addicts have made the drug while
driving.[106] Producing methamphetamine in this fashion can be extremely dangerous and has been linked to several
fatalities.[107]
Methamphetamine
12
Production and distribution
Until the early 1990s, methamphetamine for the U.S.
market was made mostly in labs run by drug traffickers
in Mexico and California. Indiana state police found
1,260 labs in 2003, compared to just 6 in 1995,
although this may be partly a result of increased police
activity.[108] As of 2007, drug and lab seizure data
suggests that approximately 80 percent of the
methamphetamine used in the United States originates
from larger laboratories operated by Mexican-based
syndicates on both sides of the border and that
approximately 20 percent comes from small toxic labs
(STLs) in the United States.[109]
Industrial-scale methamphetamine and MDMA chemical factory in
Cikande, Indonesia.
Mobile and motel-based methamphetamine labs have
caught the attention of both the U.S. news media and
the police. Such labs can cause explosions and fires and
expose the public to hazardous chemicals. Those who
manufacture methamphetamine are often harmed by
toxic gases. Many police departments have specialized
task forces with training to respond to cases of
methamphetamine production. The National Drug
Threat Assessment 2006, produced by the Department
of
Justice,
found
"decreased
domestic
methamphetamine production in both small and
large-scale laboratories", but also that "decreases in
domestic methamphetamine production have been
offset by increased production in Mexico." The report
concluded that "methamphetamine availability is not
likely to decline in the near term."[110]
In July 2007, Mexican officials at the port of Lázaro
Cárdenas seized a ship carrying 19 tons of
pseudoephedrine, a raw material needed for
methamphetamine.[111] The shipment originated in Hong Kong and passed through the United States at the port of
Long Beach prior to its arrival in Mexico.
One pound of methamphetamine, discovered on a
passenger at LAX airport.
In the United States, illicit methamphetamine comes in a variety of forms with prices varying widely over time.[112]
Most commonly, it is found as a colorless crystalline solid. Impurities may result in a brownish or tan color. Colorful
flavored pills containing methamphetamine and caffeine are known as yaa baa (Thai for "crazy medicine").
An impure form of methamphetamine is sold as a crumbly brown or off-white rock, commonly referred to as "peanut
butter crank".[113] Methamphetamine found on the street is rarely pure, but adulterated with chemicals that were used
to synthesize it. It may be diluted or cut with non-psychoactive substances like inositol, isopropylbenzylamine or
dimethylsulfone. Another popular method is to combine methamphetamine with other stimulant substances, such as
caffeine or cathine, into a pill known as a "Kamikaze", which can be particularly dangerous due to the synergistic
effects of multiple stimulants. It may also be flavored with high-sugar candies, drinks, or drink mixes to mask the
bitter taste of the drug. Coloring may be added to the meth, as is the case with "Strawberry Quick".[114] [115]
Methamphetamine
Natural occurrence
Methamphetamine has been reported to occur naturally in Acacia berlandieri, and possibly Acacia rigidula, trees
that grow in West Texas.[116] Methamphetamine and regular amphetamine were long thought to be strictly
human-synthesized,[117] but Acacia trees contain these and numerous other psychoactive compounds (e.g.,
mescaline, nicotine, dimethyltryptamine), and the related compound β-phenethylamine is known to occur from
numerous Acacia species.[118]
Terminology
Nicknames for methamphetamine are numerous and vary from region to region.
USA nicknames
Some common nicknames in the USA include "Snap,Crackle,Pop" "meth," "ice," "crystal," "crystal meth," "go," "go
fast," "Okie coke," and "tweak." Other referenced nicknames in the U.S. are "poor man's cocaine"[119] and
"Tina".[120]
Methamphetamine may also be referred to as "speed", a nickname that is commonly used for amphetamine (in
racemic or dextrorotary form), which differs from methamphetamine by the absence of a methyl group in its
chemical formula.[121]
It is also known as "batu" or "batunas" on Hawaii.[122] In the middle east it is known as "roni, ronin" or "bibo"
Nicknames in other countries
•
•
•
•
•
•
•
•
•
•
•
•
"ice" (Australia)[123]
"tik" (South Africa)[124]
"bato" (Philippines)[122]
"vint" (Russian for "a screw" (Russia))[125]
"ya ice" (Thai for "Ice drug" (Thailand))
"P" (from the "p" in "pure" (New Zealand))[126]
"필로폰" (Korean for "Philopon" (South Korea))
"shabu" (Japan, Hong Kong, Philippines, Malaysia)
"batu kilat" (Malaysian for "shining rocks" (Malaysia))[122]
"piko" (after the trade name "Pervitin" (Czech Republic))
"peří" (in translation "Feathers" phonetically similar to "Pervitin" (Czech Republic))
"perník" (in translation "gingerbread" phonetically similar to "Pervitin" (Czech Republic))
Legality
The production, distribution, sale, and possession of methamphetamine is restricted or illegal in many jurisdictions.
Methamphetamine has been placed in Schedule II of the United Nations Convention on Psychotropic Substances
treaty.[127]
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Further reading
• Yudko, Errol; McPherson, Sandra; Hall, Harold (2008-10-29). Methamphetamine Use: Clinical and Forensic
Aspects (http://search.barnesandnoble.com/booksearch/isbninquiry.asp?ean=9780849372735&
box=978-0849372735&pos=-1). 408 (2 ed.). Boca Raton, FL: CRC Press. ISBN 978-0849372735.
External links
• NLM Hazardous Substances Data Bank (http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+
@rn+@rel+537-46-2) - Entry for d-methamphetamine
• Desoxyn (http://www.lundbeckinc.com/USA/products/CNS/desoxyn/default.asp) - Prescription form of the
drug.
• Erowid Methamphetamine Vault (http://www.erowid.org/chemicals/meth/meth.shtml)
• EMCDDA drugs profiles: Methamphetamine (2007) (http://www.emcdda.europa.eu?nnodeid=25480)
• EMCDDA paper on Methamphetamine supply in Europe (2009) (http://laniel.free.fr/INDEXES/BooksIndex/
METH OEDT/Meth_OEDT_Sommaire.htm)
• A Key to Methamphetamine-Related Literature (http://www.nyhealth.gov/diseases/aids/harm_reduction/
crystalmeth/docs/meth_literature_index.pdf) - A comprehensive thematic index of methamphetamine research
published in academic and scientific journals with links from citations to the PubMed abstracts.
•
•
•
•
•
•
•
• Meth FAQ (http://www.erowid.org/chemicals/meth/meth_faq.shtml#synthesis) - More detailed synthesis
and synthesis from other sources.
DEA's Methamphetamine News Releases (http://www.usdoj.gov/dea/pubs/pressrel/meth_index.html)
Poison Information Monograph (http://www.inchem.org/documents/pims/pharm/pim334.htm) (PIM 334:
Methamphetamine)
Chronic Amphetamine Use and Abuse (http://www.acnp.org/g4/GN401000166/Default.htm) - A thorough
review on the effects of chronic use (American College of Neuropsychopharmacology)
Self-help guide for family members and loved ones of methamphetamine addicts (http://methcoaster.yolasite.
com/)
U.S. National Library of Medicine: Drug Information Portal - Methamphetamine (http://druginfo.nlm.nih.gov/
drugportal/dpdirect.jsp?name=Methamphetamine)
ChemSub Online: Methamphetamine (http://chemsub.online.fr/name/methamphetamine.html)
Mice On Meth (http://www.educatedearth.net/video.php?id=4326) - Video of mice suffering from
methamphetamine addiction.
18
Methamphetamine
Documentaries
• The Ice Age (http://abc.net.au/4corners/special_eds/20060320/) - ABC Australia - 4 Corners — Australian
methamphetamine use.
• Frontline - The Meth Epidemic (http://www.pbs.org/wgbh/pages/frontline/meth/) - PBS United States —
Frontline.
• The World's Most Dangerous Drug (http://shop.nationalgeographic.com/product/1167/3408/1074.html) National Geographic.
• The City Addicted to Crystal Meth - BBC (Louis Theroux) (http://www.bbc.co.uk/iplayer/episode/
b00m572d/Louis_Theroux_The_City_Addicted_to_Crystal_Meth)
Academic Sources
• History and Epidemiology of Amphetamine Abuse in United States (http://books.google.com/books?hl=en&
lr=&id=gVw_wzZU4x8C&oi=fnd&pg=PA113&dq=history+methamphetamine&ots=qAxtq4m1HZ&
sig=najz_xcJJ782gsd41TEqXm40igo#v=onepage&q=history methamphetamine&f=false)
• Methamphetamine, the Crystal Method, and the War on Drugs (http://law.bepress.com/expresso/eps/639/)
• The Methamphetamine Crisis in American Indian and Native Alaskan Communities (http://studentpulse.com/
articles/77/
the-methamphetamine-crisis-in-american-indian-and-native-alaskan-communities-toward-a-new-research-agenda)
19
Article Sources and Contributors
Article Sources and Contributors
Methamphetamine Source: http://en.wikipedia.org/w/index.php?oldid=418900180 Contributors: 16x9, 17Drew, 2112iceman, 2D, 2help, 5 albert square, 78UnicornBrina, 97198, 9dephillis, A
Softer Answer, A. Parrot, A8UDI, A930913, ABCD, ABF, ABrundage, AMX, AThing, Aaron Brenneman, AaronRosenberg, Abrightcoldday, Abrooke, Acabtp, Academic Challenger,
Acroterion, Adagio, Adam McMaster, Adam.J.W.C., Ahoerstemeier, Aillema, Aitias, Ajwitney, Akersmc, Alan Liefting, Alan Rockefeller, Alansohn, Albert109, Alexander Iwaschkin, Algae,
Alhutch, Alias Flood, AllGloryToTheHypnotoad, Allison Stillwell, Allyn, Alodyne, Alpha Quadrant (alt), Alphaquad, Alvis, Alwaysasking, Alxndr, Alyaly94, Amazon10x, Anchoress,
Andrea105, Andrew73, Andrewlp1991, Andy5421, Andypham3000, Angel caboodle, Angieb1728, Angr, Animum, Ann Stouter, Anna Frodesiak, Annetterj, Anonymous editor,
Ansbachdragoner, Antaeus Feldspar, Antandrus, Anthelion, Anthony Appleyard, Anthonyhcole, Anxietycello, Anypodetos, Aphid360, Aplomado, Apollogroove, AppleNick, Arakunem,
Aramgutang, Ardg08, Aremith, Arichnad, Arohanui, Aron1, Arrowfrog amped, Artaxiad, ArthurDenture, Aruton, Asalazaro, Ashlux, Ashumeetsingh, Ask123, Astanhope, Astral Zen, Atif.t2,
Atlant, Atombomb, Atrain472, Attys, AubreyEllenShomo, Aude, Audiosmurf, August Potential, Auton1, Avoided, AxelBoldt, Axeman89, Azazell0, B. Fairbairn, BalthCat, Banime, Barbatus,
Barefootguru, Barrykmorris, Barticus88, Bastique, Bataluis, Bayhemp, Bdell555, Beefman, Beetstra, Beland, Belbo Casaubon, Ben Arnold, Benandorsqueaks, Benbread, Bender235,
Benjah-bmm27, Benjiboi, Benjiwolf, Bento00, Benvogel, Benwedge, Bestlyriccollection, Bettia, Bgpaulus, BigBadaboom0, Bigkev, Billwhittaker, Birlanady, Bk0, Black Kite, Blaireaux,
Blchrist, Blinkfreak182, Blobglob, Blue520, Bluerasberry, Bobmack89x, Bobo192, Bobomatic, Bogey97, Bombyx, Bonecrushah, Bongwarrior, Bonus Onus, BorgQueen, BorisTM, Bornhj,
Boston, Bovineone, Bradby, Brainmuncher, Brandon, Brandon will03, Brant.irons, Brevmhoy, Brianga, Brianski, Bronayur, Brooker, Brucestaffxxx, Bryan Derksen, Bubby the Tour G, Bubeck,
Bulldog 466, Bundybear22, Burleigh2, Burningview, Burntsauce, ButOnMethItIs, Butros, Bxj, C6541, CIreland, CJ, CKelly, COMPFUNK2, CSWarren, Cacycle, Cadmium, Cahk,
Cajolingwilhelm, Caknuck, Calmer Waters, Caltas, CambridgeBayWeather, Can't sleep, clown will eat me, Canderson7, CanisRufus, Capricorn42, Capt. James T. Kirk, Careless hx, Carleas,
Carlmoe, Casforty, Casito, Castlemj, Cath0de, Centrx, Ceyockey, Charlesdrakew, ChemNerd, Chewzz, Chibps, ChicXulub, Chickenfeathers, Chovain, Chowbok, Chris 73, Chris Capoccia, Chris
Henniker, Chris Longley, Chris b shanks, Chris the speller, Chris9181, Chrislk02, ChristopherM, CiTrusD, Ciphergoth, Cit helper, Cjas, Clarince63, Cliff smith, CliffC, Closedmouth, Clovis
Sangrail, Cmichael, Codetiger, Cogorno, ConMan, Corentinoger, Corvus cornix, CosmicFalcon, Countmippipopolous, Courcelles, Crazy Wolf, Crazycanuck, Crazym108, Crimsone, Critical Info,
Crystallina, Crywalt, Csab, Cst17, Ctjf83, Cubs Fan, Cunningham, Curtholr, Cybercobra, Cyberfunk, DARTH SIDIOUS 2, DJBullfish, DMacks, DTM, DVD R W, Da Joe, Da nuke, Dabomb87,
Dale Arnett, Damianhamliness, Damicatz, DancingMan, DancingPenguin, Danger, Daniel Brockman, DanielDeibler, Danski14, Dante Alighieri, Danthemankhan, Dar-Ape, DarkShroom, Darth
Panda, Dasune, David.Monniaux, Davidknippers, Davidmpye, Davidruben, Davidwr, Dawn Bard, Dbfirs, Dbratland, Dbtfz, Dcflyer, Dcooper, Ddhix 2002, Ddoomdoom, De728631, Debresser,
Dedust57, Demonkey36, Den99hd, Deor, DerHexer, DerechoReguerraz, Detourne, Devourer09, Dg7891, Dhcodnsdlqslek, Dhollm, Dicklyon, Digdan, Dikjosef, Dina, Dinglu14, Dippit, Dirk
Gently, Discospinster, Dismas, Djbaniel, Djhofrich, Djramone, Djtophat12, Dkedke, Dmackie, Dmjames, Dmod, Dobermanji, DocWatson42, Doctormatt, Doktordoris, DonCalo, Donama,
Donmike10, Doops, DoriSmith, DoubleBlue, Doug Bell, Dr Dec, Dr Ishmael, Dr. Bernice, Dr. Ke, DrHouse09, Dragon76, DragonflySixtyseven, Dragoon93, Drc79, Drisdred, Drphilharmonic,
Drumguy8800, Drunkenmonkey, DryGrain, Dsi2104, Dtmcquade, Dueche, Dureo, Durnienp, Dysprosia, EJF, ESkog, EamonnPKeane, Earfetish1, Ebonyks, Eclipsed Moon, Eco84, Ed
Fitzgerald, Edgar181, Edgarde, Edgeris, Editor182, Edivorce, Edward Bower, Eeekster, Eequor, Eggishorn, Eggroll65, Ehengmay, Ehn, El3ctr0nika, Elfzx3, Eliz81, Elkman, Eloil, Emdx,
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Boy, Eyeon, FF2010, FT2, Fabiform, Fade, Falcon Kirtaran, Falcon8765, Falcon9x5, FalloutFan15, Faradayplank, Faseidman, Fastily, Fastman99, FatalError, Favonian, FayssalF, Feinoha,
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Kendysz, Jakessister, James086, JamesAM, Jason M, Jasonglchu, Jawed, Jay Gatsby, Jayjay21, Jbob06, Jcrock, Jeff G., Jeffalex, Jeffy Raccoon, Jennavecia, Jeof0411, Jeremiahbell, Jesster79,
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Julesd, Junglecat, Junior Brian, Jusdafax, Justsail, KMFDM Fan, Kanodin, KarlM, Karn, Kartano, Katalaveno, Kathartic, Katieh5584, Kbdank71, Kbh3rd, Keapontruckin, Keith D, Kellyhuen,
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Kyle1278, L Kensington, La goutte de pluie, Lakers, Lancer8869, Lapaz, Larry Yuma, Laudaka, Laurinavicius, Layonard, Lazypplunite, Lcolonna, LeaveSleaves, Lemnpies2, Lemontune, Lerix,
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Image Sources, Licenses and Contributors
Image Sources, Licenses and Contributors
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file:Methamphetamine-3d-CPK.png Source: http://en.wikipedia.org/w/index.php?title=File:Methamphetamine-3d-CPK.png License: Creative Commons Attribution-Sharealike 2.5
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Kwj2772, MGA73, Mardetanha, Penubag, Pseudomoi, WikipediaMaster, 1 anonymous edits
Image:Blue Crystal Meth .jpg Source: http://en.wikipedia.org/w/index.php?title=File:Blue_Crystal_Meth_.jpg License: Public Domain Contributors: User:Psychonaught
File:Meth lab.jpg Source: http://en.wikipedia.org/w/index.php?title=File:Meth_lab.jpg License: Creative Commons Attribution-Sharealike 3.0 Contributors: User:Billwhittaker
Image:methamphetamine2.png Source: http://en.wikipedia.org/w/index.php?title=File:Methamphetamine2.png License: Public Domain Contributors: User:SubDural12
Image:Deux pilules de Desoxyn Gradumet 10mg.jpg Source: http://en.wikipedia.org/w/index.php?title=File:Deux_pilules_de_Desoxyn_Gradumet_10mg.jpg License: Public Domain
Contributors: Harbinary, Octavio L, Sanao, 2 anonymous edits
Image:Méthamphétamine pure.jpg Source: http://en.wikipedia.org/w/index.php?title=File:Méthamphétamine_pure.jpg License: Public Domain Contributors: United States Federal
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Image:methjakarta.jpg Source: http://en.wikipedia.org/w/index.php?title=File:Methjakarta.jpg License: Public Domain Contributors: Original uploader was Miserlou at en.wikipedia
File:Pound of methamphetamine .jpg Source: http://en.wikipedia.org/w/index.php?title=File:Pound_of_methamphetamine_.jpg License: Public Domain Contributors: U.S. Department of
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21

Methamphetamine - Department of Electrical Engineering

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