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Heroin
Systematic (IUPAC) name
(5α,6α)-7,8-didehydro- 4,5-epoxy- 17-methylmorphinan- 3,6-diol diacetate
Identifiers
CAS number	561-27-3
ATC code	N02AA09
PubChem	5462328
ChemSpider	4575379
Chemical data
Formula	C21H23NO5
Mol. mass	369.41
Synonyms	Diamorphine, Diacetylmorphine, Acetomorphine, (Dual) Acetylated morphine, Morphine diacetate
Pharmacokinetic data
Bioavailability	<35% (oral), 44–61% (inhaled)[1]
Protein binding	0% (morphine metabolite 35%)
Metabolism	hepatic
Half life	3–5 min (IV, inhaled)[2]
Excretion	90% renal as glucuronides, rest biliary
Therapeutic considerations
Pregnancy cat.	Category X
Legal status	Prohibited (S9)(AU) Schedule I(CA) Class A(UK) Schedule I(US)
Dependence Liability	Extremely High
Routes	Inhalation, Transmucosal, Intravenous, Oral, Intranasal, Rectal, Intramuscular

Diacetylmorphine (INN), also known as diamorphine (BAN) and heroin, is a semi-synthetic opioid drug synthesized from morphine, a derivative of the opium poppy. It is the 3,6-diacetyl ester of morphine (hence diacetylmorphine). The white crystalline form is commonly the hydrochloride salt diacetylmorphine hydrochloride, however heroin freebase may also appear as a white powder.

As with other opioids, diacetylmorphine is used as both a pain-killer and a recreational drug and has high potential for abuse. Frequent and regular administration is associated with tolerance, moderate physical dependence, and severe psychological dependence with potential to develop into addiction.

Internationally, diacetylmorphine is controlled under Schedules I and IV of the Single Convention on Narcotic Drugs.^[1] It is illegal to manufacture, possess, or sell diacetylmorphine without a licence in Belgium, Denmark, Germany, Iran, India, the Netherlands, the United States, Australia, Canada, Ireland, Pakistan, the United Kingdom and Swaziland. Under the name diamorphine, it is a legally prescribed controlled drug in the United Kingdom. In the Netherlands, under the name diacetylmorphine, it is available for prescription to long-term addicts. Popular street names for the drug include black tar, skag, horse, smack, Junk, chieva, gear, Evil, "H", "Boy", "Big Boy", "dog food,'baby powder' 'brownstone'" and others.

Contents 1 History 2 Pharmacology 3 Usage and effects 3.1 Medical use 3.2 Recreational use 3.3 Effects 4 Regulation 5 Price 6 Production and trafficking: The Golden Triangle 6.1 Manufacturing 6.2 History of heroin traffic 6.3 Trafficking 7 Risks of use 8 Harm reduction approaches to heroin 9 Withdrawal 10 Heroin prescription 11 Controversy 12 Popular culture 12.1 Literature 12.2 Musicians who have used, or written about, heroin use 12.3 Film 13 See also 14 References 15 Literature 16 External links

[edit] History

The opium poppy was cultivated in lower Mesopotamia as long ago as 3400 BC.^[2] The chemical analysis of opium in the 19th century revealed that most of its activity could be ascribed to two alkaloids, codeine and morphine.

Diacetylmorphine was first synthesized in 1874 by C. R. Alder Wright, an English chemist working at St. Mary's Hospital Medical School in London, England. He had been experimenting with combining morphine with various acids. He boiled anhydrous morphine alkaloid with acetic anhydride over a stove for several hours and produced a more potent, acetylated form of morphine, now called diacetylmorphine. The compound was sent to F. M. Pierce of Owens College in Manchester for analysis, who reported the following to Wright:

Doses ... were subcutaneously injected into young dogs and rabbits ... with the following general results ... great prostration, fear, and sleepiness speedily following the administration, the eyes being sensitive, and pupils constrict, considerable salivation being produced in dogs, and slight tendency to vomiting in some cases, but no actual emesis. Respiration was at first quickened, but subsequently reduced, and the heart's action was diminished, and rendered irregular. Marked want of coordinating power over the muscular movements, and loss of power in the pelvis and hind limbs, together with a diminution of temperature in the rectum of about 4° (rectal failure).^[3]

Wright's invention, however, did not lead to any further developments, and diacetylmorphine only became popular after it was independently re-synthesized 23 years later by another chemist, Felix Hoffmann. Hoffmann, working at the Bayer pharmaceutical company in Elberfeld, Germany, was instructed by his supervisor Heinrich Dreser to acetylate morphine with the objective of producing codeine, a constituent of the opium poppy, similar to morphine pharmacologically but less potent and less addictive. But instead of producing codeine, the experiment produced an acetylated form of morphine that was one and a half to two times more potent than morphine itself. Bayer would name the substance "heroin", probably from the word heroisch, German for heroic, because in field studies people using the medicine felt "heroic".^[4]

From 1898 through to 1910, under the name heroin, diacetylmorphine was marketed as a non-addictive morphine substitute and cough suppressant. Bayer marketed heroin as a cure for morphine addiction before it was discovered that it is rapidly metabolized into morphine, and as such, heroin was essentially a quicker acting form of morphine. The company was embarrassed by this new finding and it became a historic blunder for Bayer.^[5]

As with aspirin, Bayer lost some of its trademark rights to "heroin" under the 1919 Treaty of Versailles following the German defeat in World War I.^[6]

In the U.S.A. the Harrison Narcotics Tax Act was passed in 1914 to control the sale and distribution of "heroin" and other opioids. This law did allow the drug to be prescribed and sold for medical purposes. In 1924, the United States Congress passed additional legislation banning the sale, importation or manufacture. It is now a Schedule I substance, and is thus illegal in the United States.

[edit] Pharmacology

When taken orally, diacetylmorphine undergoes extensive first-pass metabolism via deacetylation, making it a prodrug for the systemic delivery of morphine.^[7] When the drug is injected, however, it avoids this first-pass effect, very rapidly crossing the blood-brain barrier due to the presence of the acetyl groups, which render it much more lipid-soluble than morphine itself.^[8] Once in the brain, it then is deacetylated into 6-monoacetylmorphine (6-MAM) and morphine which bind to μ-opioid receptors, resulting in the drug's euphoric, analgesic (pain relief), and anxiolytic (anti-anxiety) effects; diacetylmorphine itself exhibits relatively low affinity for the μ receptor.^[9] Unlike hydromorphone and oxymorphone, however, administered intravenously, diacetylmorphine creates a larger histamine release, similar to morphine, resulting in the feeling of a greater subjective "body high" to some, but also instances of pruritus (itching) when they first start using .^[10]

Both morphine and 6-MAM are μ-opioid agonists which bind to receptors present throughout the brain, spinal cord and gut of all mammals. The μ-opioid receptor also binds endogenous opioid peptides such as β-endorphin, Leu-enkephalin, and Met-enkephalin. Repeated use of diacetylmorphine results in a number of physiological changes, including decreases in the number of μ-opioid receptors.^{[citation needed]} These physiological alterations lead to tolerance and dependence, so that cessation of diacetylmorphine use results in a set of extremely uncomfortable symptoms including pain, anxiety, muscle spasms, and insomnia called the opioid withdrawal syndrome. Depending on usage it has an onset 4 to 24 hours after the last dose of diacetylmorphine. Morphine also binds to δ- and κ-opioid receptors.

There is also evidence that 6-MAM binds to a subtype of μ-opioid receptors which are also activated by the morphine metabolite morphine-6β-glucuronide but not morphine itself.^[11] The contribution of these receptors to the overall pharmacology of heroin remains unknown.

[edit] Usage and effects

[edit] Medical use

Under the name diamorphine, diacetylmorphine is prescribed as a strong analgesic in the United Kingdom, where it is given via subcutaneous, intramuscular or intravenous route. Its use includes treatment for acute pain, such as in severe trauma, myocardial infarction, and following surgery, and chronic pain, including in cancer. In other countries it is more common to use morphine or other strong opioids in these situations.

In 2005, there was a shortage of diamorphine in the UK, due to a problem at the main UK manufacturers.^[12] Due to this, many hospitals changed to using morphine instead of diamorphine. Although there is no longer a problem with its manufacture, many hospitals have continued to use morphine.

Diamorphine is continued to be widely used in palliative care in the United Kingdom, where it is commonly given by the subcutaneous route, often via a syringe driver, if patients could not easily swallow oral morphine solution. The advantage of diamorphine over morphine is that diamorphine is more soluble and smaller volumes of diamorphine are needed for the same analgesic effect. Both of these factors are advantageous if giving high doses of opioids via the subcutaneous route, which is often necessary in palliative care.

The medical use of diamorphine (in common with other strong opioids such as morphine, fentanyl and oxycodone) is controlled in the United Kingdom by the Misuse of Drugs Act 1971. It is a schedule 2 controlled drug, and registers of its use are required to be kept in hospitals, and prescriptions for its use must be written with the form and strength of the preparation, and quantity stated in both words and figures.

[edit] Recreational use

Diacetylmorphine is used as a recreational drug for the profound relaxation and intense euphoria it produces, although the latter effect diminishes with increased tolerance. Its popularity with recreational drug users, compared to morphine, reportedly stems from its perceived different effects.^[13] In particular, users report an intense "rush" that occurs while the diacetylmorphine is being metabolized into 6-monoacetylmorphine (6-MAM) and morphine in the brain. Any intravenous opioid will induce rapid, profound effects, but diacetylmorphine produces more euphoria than other opioids upon injection. One possible explanation is the presence of 6-monoacetylmorphine, a metabolite unique to diacetylmorphine. While other opioids of abuse, such as codeine, produce only morphine, heroin also leaves 6-MAM, also a psycho-active metabolite. However, this perception is not supported by the results of clinical studies comparing the physiological and subjective effects of injected diacetylmorphine and morphine in individuals formerly addicted to opioids; these subjects showed no preference for one drug over the other. Equipotent, injected doses had comparable action courses, with no difference in subjects' self-rated feelings of euphoria, ambition, nervousness, relaxation, drowsiness, or sleepiness.^[14] Short-term addiction studies by the same researchers demonstrated that tolerance developed at a similar rate to both diacetylmorphine and morphine. When compared to the opioids hydromorphone, fentanyl, oxycodone, and pethidine/meperidine, former addicts showed a strong preference for diacetylmorphine and morphine, suggesting that diacetylmorphine and morphine are particularly susceptible to abuse and addiction. Morphine and diacetylmorphine were also much more likely to produce euphoria and other positive subjective effects when compared to these other opioids.^[14]

One of the most common methods of illicit diacetylmorphine use is via intravenous injection (colloquially termed "shooting up"). Heroin base (commonly found in the UK and Europe), when prepared for injection will only dissolve in water when mixed with an acid (most commonly citric acid powder or lemon juice) and heated. Heroin in the US is most commonly its hydrochloride salt, requiring just water to dissolve. Users tend to initially inject in the easily accessible veins in the arm, but as these veins collapse over time through damage caused by the acid, the user will often resort to injecting in other veins such as those in the legs, groin or neck.

Recreational users may also administer the drug through means of snorting, or smoking by inhaling its vapors when heated; either with tobacco in a rolled cigarette or by heating the drug on aluminium foil from underneath. When heated the heroin powder changes to a thick liquid, similar in consistency to molten wax, and it will run across the foil giving off smoke which the user inhales through a tube, usually made from foil also so that any heroin that collects on the inside of the tube can be smoked afterward. The user follows the "blob" of heroin with the intention of inhaling, through the tube, as much of the smoke as possible - i.e. "chasing the dragon."

The onset of diacetylmorphine's effects depends upon the route of administration. Orally, since diacetylmorphine is completely metabolized in vivo to morphine before crossing the blood-brain barrier the effects are the same as with oral morphine. Snorting results in an onset within 3 to 5 minutes; smoking results in an almost immediate effect that builds in intensity; intravenous injection induces a rush and euphoria usually taking effect within 30 seconds; intramuscular and subcutaneous injection take effect within 3 to 5 minutes.

The diacetylmorphine dose used for recreational purposes depends strongly on the frequency of use. A first-time user typically ingests between 5 and 20 mg of diacetylmorphine, but an individual who is heavily dependent on the drug may require several hundred mg per day.^[15]

Large doses of diacetylmorphine can cause fatal respiratory depression, and the drug has been used for suicide or as a murder weapon. The serial killer Dr Harold Shipman used it on his victims as did Dr John Bodkin Adams (see his victim, Edith Alice Morrell). Because significant tolerance to respiratory depression develops quickly with continued use and is lost just as quickly during withdrawal, it is often difficult to determine whether a diacetylmorphine death was an accident, suicide or murder. Examples include the overdose deaths of Sid Vicious, Janis Joplin, Tim Buckley, Layne Staley, Bradley Nowell, Jim Morrison, and Ted Binion.^[16]

[edit] Effects

Central nervous system:

• Drowsiness
• Disorientation
• Delirium

Cardiovascular & Respiratory:

• Bradycardia
• Hypotension
• Hypoventilation
• Shallow breathing
• Respiratory depression

Eyes, Ears, mouth, and nose:

• Dry mouth (Xerostomia)
• Miosis, or pupil constriction ("pinpoint pupils")

Gastrointestinal:

• Nausea
• Vomiting (protracted)
• Constipation
• Dyspepsia

Urinary System:

• Urinary retention

Musculoskeletal:

• Analgesia
• Ataxia
• Muscle spasticity

Neurological:

• Analgesia
• Physical dependence

Psychological:

• Anxiolysis
• Confusion
• Euphoria
• Psychological dependence
• Somnolence

Skin:

• Itching
• Flushing/Rash

Indicated for: Relief of Extreme Pain Recreational uses: Euphoria Relaxation Other uses: Pain relief Cough suppressant anti-diarrheal

Contraindications: Alcohol Barbiturates and Benzodiazepines Stimulants Other opioids (depends heavily on tolerance)

[edit] Regulation

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In the Netherlands, diamorphine (heroin) is a List I drug of the Opium Law. It is available for prescription under tight regulation to long-term heroin addicts for whom methadone maintenance treatment has failed. Heroin is exclusively available for prescription to long-term heroin addicts, and cannot be used to treat severe pain or other illnesses.

In the United States, heroin is a schedule I drug according to the Controlled Substances Act of 1970, making it illegal to possess without a DEA license. Possession of more than 100 grams of heroin or a mixture containing heroin is punishable with a minimum mandatory sentence of 5 years of imprisonment in a federal prison.

In Canada, heroin is a controlled substance under Schedule I of the Controlled Drugs and Substances Act (CDSA). Any person who seeks or obtains heroin without disclosing authorization 30 days prior to obtaining another prescription from a practitioner is guilty of an indictable offense and subject to imprisonment for a term not exceeding seven years. Possession of heroin for the purpose of trafficking is guilty of an indictable offense and subject to imprisonment for life.

In Hong Kong, heroin is regulated under Schedule 1 of Hong Kong's Chapter 134 Dangerous Drugs Ordinance. It is available by prescription. Anyone who supplies heroin without a valid prescription can be fined $10,000 (HKD). The penalty for trafficking or manufacturing heroin is a $5,000,000 (HKD) fine and life imprisonment. Possession of heroin without a license from the Department of Health is illegal with a $1,000,000 (HKD) fine and/or 7 years of jail time.

In the United Kingdom, heroin is available by prescription, though it is a restricted Class A drug. According to the 50th edition of the British National Formulary (BNF), diamorphine hydrochloride may be used in the treatment of acute pain, myocardial infarction, acute pulmonary oedema, and chronic pain. The treatment of chronic non-malignant pain must be supervised by a specialist. The BNF notes that all opioid analgesics cause dependence and tolerance but that this is "no deterrent in the control of pain in terminal illness". When used in the palliative care of cancer patients, heroin is often injected using a syringe driver.

[edit] Price

The European Monitoring Centre for Drugs and Drug Addiction reports that the retail price of brown heroin varies from 14.5€ per gram in Turkey to 110€ per gram in Sweden, with most European countries reporting typical prices of 45-55€ per gram. The price of white heroin is reported only by a few European countries and ranged between 27€ and 110€ per gram.^[18]

The United Nations Office on Drugs and Crime claims in its 2008 World Drug Report that typical US retail prices are 172 dollars per gram.^[19]

[edit] Production and trafficking: The Golden Triangle

[edit] Manufacturing

Heroin is produced for the black market by refining opium. The first step of this process involves isolation of morphine from opium. This crude morphine is then acetylated by heating with acetic anhydride. Purification of the obtained crude heroin and conversion to the hydrochloride salt results in a water-soluble form of the drug that is a white or yellowish powder.

Crude opium is carefully dissolved in hot water but the resulting hot soup is not boiled. Mechanical impurities - twigs - are scooped together with the foam. The mixture is then made alkaline by gradual addition of lime. Lime causes a number of unwelcome components present in opium to precipitate out of the solution. (The impurities include inactive alkaloids, resins, proteins). The precipitate is removed by filtration through a cloth, washed with additional water and discarded. The filtrates containing the water-soluble calcium salt of morphine (calcium morphinate) are then acidified by careful addition of ammonium chloride. This causes morphine (as a free phenol) to precipitate. The morphine precipitate is collected by filtration and dried before the next step. The crude morphine (which makes only about 10% of the weight of opium) is then heated together with acetic anhydride at 85 °C (185 °F) for six hours. The reaction mixture is then cooled, diluted with water, made alkaline with sodium carbonate, and the precipitated crude heroin is filtered and washed with water. This crude water-insoluble freebase product (which by itself is usable, for smoking) is further purified and decolorised by dissolution in hot alcohol, filtration with activated charcoal and concentration of the filtrates. The concentrated solution is then acidified with hydrochloric acid, diluted with ether, and the precipitated heroin hydrochloride is the purest form of heroin collected by filtration. This precipitate is the so-called "no. 4 heroin", commonly known as "china white". China white is heroin in its purest form. Heroin freebase cut with a small amount of caffeine (to help vaporise it more efficiently), typically brown in appearance, is known as "no. 3 heroin". These two forms of heroin are the standard products exported to the Western market. Heroin no. 3 predominates on the European market, where heroin no. 4 is relatively uncommon. Another form of heroin is "black tar" which is common in the western United States and is produced in Mexico.

The initial stage of opium refining—the isolation of morphine—is relatively easy to perform in rudimentary settings - even by substituting suitable fertilizers for pure chemical reagents. However, the later steps (acetylation, purification, and conversion to the hydrochloride salt) are more involved—they use large quantities of chemicals and solvents and they require both skill and patience. The final step is particularly tricky as the highly flammable ether can easily ignite during positive-pressure filtration (the explosion of vapor-air mixture can obliterate the refinery). If the ether does ignite, the result is a catastrophic explosion.

[edit] History of heroin traffic

This section may contain original research or unverified claims. Please improve the article by adding references. See the talk page for details. (September 2007)

The origins of the present international illegal heroin trade can be traced back to laws passed in many countries in the early 1900s that closely regulated the production and sale of opium and its derivatives including heroin. At first, heroin flowed from countries where it was still legal into countries where it was no longer legal. By the mid-1920s, heroin production had been made illegal in many parts of the world. An illegal trade developed at that time between heroin labs in China (mostly in Shanghai and Tianjin) and other nations. The weakness of government in China and conditions of civil war enabled heroin production to take root there. Chinese triad gangs eventually came to play a major role in the heroin trade. French Connection route started in the 1930s.

Heroin trafficking was virtually eliminated in the U.S. during World War II due to temporary trade disruptions caused by the war.^{[citation needed]} Japan's war with China had cut the normal distribution routes for heroin and the war had generally disrupted the movement of opium.^{[citation needed]}

After World War II, the Mafia took advantage of the weakness of the postwar Italian government and set up heroin labs in Sicily.^{[citation needed]} The Mafia took advantage of Sicily's location along the historic route opium took westward into Europe and the United States.^{[citation needed]}

Large scale international heroin production effectively ended in China with the victory of the communists in the civil war in the late 1940s.^{[citation needed]} The elimination of Chinese production happened at the same time that Sicily's role in the trade developed.

Although it remained legal in some countries until after World War II, health risks, addiction, and widespread abuse led most western countries to declare heroin a controlled substance by the latter half of the 20th century.

In late 1960s and early 70s, the CIA supported anti-Communist Chinese Nationalists settled near Sino-Burmese border and Hmong tribesmen in Laos. This helped the development of the Golden Triangle opium production region, which supplied about one-third of heroin consumed in US after 1973 American withdrawal from Vietnam. As of 1999, Myanmar (former Burma), the heartland of the Golden Triangle remained the second largest producer of heroin, after Afghanistan.^[20]

Soviet-Afghan war led to increased production in the Pakistani-Afghani border regions, as U.S.-backed mujaheddin militants raised money for arms from selling opium, contributing heavily to the modern Golden Crescent creation. By 1980, 60% of heroin sold in the U.S. originated in Afghanistan.^[20] It increased international production of heroin at lower prices in the 1980s. The trade shifted away from Sicily in the late 1970s as various criminal organizations violently fought with each other over the trade. The fighting also led to a stepped up government law enforcement presence in Sicily.

[edit] Trafficking

See also: Opium production

Traffic is heavy worldwide, with the biggest producer being Afghanistan.^[21] According to U.N. sponsored survey,^[22] as of 2004^[update], Afghanistan accounted for production of 87 percent of the world's heroin.^[23]

The cultivation of opium in Afghanistan reached its peak in 1999, when 225,000 acres - 350 square miles - of poppies were sown. The following year the Taliban banned poppy cultivation, a move which cut production by 94 percent. By 2001 only 30 square miles of land were in use for growing opium poppies. A year later, after American and British troops had removed the Taliban and installed the interim government, the land under cultivation leapt back to 285 square miles, with Afghanistan supplanting Burma to become the world's largest opium producer once more. ^[24] Opium production in that country has increased rapidly since, reaching an all-time high in 2006. War once again appeared as a facilitator of the trade.^[25]

At present, opium poppies are mostly grown in Afghanistan, and in Southeast Asia, especially in the region known as the Golden Triangle straddling Myanmar, Thailand, Vietnam, Laos and Yunnan province in the People's Republic of China. There is also cultivation of opium poppies in the Sinaloa region of Mexico and in Colombia. The majority of the heroin consumed in the United States comes from Mexico and Colombia. Up until 2004, Pakistan was considered one of the biggest opium-growing countries.

Conviction for trafficking in heroin carries the death penalty in most South-east Asian, some East Asian and Middle Eastern countries (see Use of death penalty worldwide for details), among which Malaysia, Singapore and Thailand are the most strict. The penalty applies even to citizens of countries where the penalty is not in place, sometimes causing controversy when foreign visitors are arrested for trafficking, for example the arrest of nine Australians in Bali, the death sentence given to Nola Blake in Thailand in 1987, or the hanging of an Australian citizen Van Tuong Nguyen in Singapore, both in 2005.

[edit] Risks of use

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• For intravenous users of heroin (and any other substance), the use of non-sterile needles and syringes and other related equipment leads to several serious risks:
  • the risk of contracting blood-borne pathogens such as HIV and hepatitis
  • the risk of contracting bacterial or fungal endocarditis and possibly venous sclerosis
  • abscesses
• Poisoning from contaminants added to "cut" or dilute heroin
• Chronic constipation
• Addiction and increasing tolerance
• Physical dependence can result from prolonged use of all opioids, resulting in withdrawal symptoms on cessation of use
• Decreased kidney function (although it is not currently known if this is due to adulterants or infectious diseases)^[26]

Many countries and local governments have begun funding programs that supply sterile needles to people who inject illegal drugs in an attempt to reduce these contingent risks and especially the contraction and spread of blood-borne diseases. The Drug Policy Alliance reports that up to 75% of new AIDS cases among women and children are directly or indirectly a consequence of drug use by injection. The United States federal government does not operate needle exchanges, although some state and local governments do support needle exchange programs.

A heroin overdose is usually treated with an opioid antagonist, such as naloxone (Narcan), or naltrexone, which has high affinity for opioid receptors but does not activate them. This reverses the effects of heroin and other opioid agonists and causes an immediate return of consciousness but may precipitate withdrawal symptoms. The half-life of naloxone is much shorter than that of most opioid agonists, so that antagonist typically has to be administered multiple times until the opioid has been metabolized by the body.

Depending on drug interactions and numerous other factors, death from overdose can take anywhere from several minutes to several hours due to anoxia because the breathing reflex is suppressed by µ-opioids. An overdose is immediately reversible with an opioid antagonist injection. Heroin overdoses can occur due to an unexpected increase in the dose or purity or due to diminished opioid tolerance. However, many fatalities reported as overdoses are probably caused by interactions with other depressant drugs like alcohol or benzodiazepines.^[27] It should also be noted that since heroin can cause nausea and vomiting, a significant number of deaths attributed to heroin overdose are caused by aspiration of vomit by an unconscious victim. Some sources give a figure of between 75 and 375 mg for a 75 kg being fatal for 50% of opiate naive people.^[28] Street heroin is of widely varying and unpredictable purity. This means that the user may prepare what they consider to be a moderate dose while actually taking far more than intended. Also, tolerance typically decreases after a period of abstinence. If this occurs and the user takes a dose comparable to their previous use, the user may experience drug effects that are much greater than expected, potentially resulting in a dangerous overdose.

It has been speculated that an unknown portion of heroin related deaths are the result of an overdose or allergic reaction to quinine, which may sometimes be used as a cutting agent.^[29]

A final factor contributing to overdoses is place conditioning. Heroin use is a highly ritualized behavior. While the mechanism has yet to be clearly elucidated, longtime heroin users display increased tolerance to the drug in locations where they have repeatedly administered heroin. When the user injects in a different location, this environment-conditioned tolerance does not occur, resulting in a greater drug effect. The user's typical dose of the drug, in the face of decreased tolerance, becomes far too high and can be toxic, leading to overdose.^[30]

A small percentage of heroin smokers and occasionally IV users may develop symptoms of toxic leukoencephalopathy. The cause has yet to be identified, but one speculation is that the disorder is caused by an uncommon adulterant that is only active when heated.^[31][32][33] Symptoms include slurred speech and difficulty walking.

Cocaine sometimes proves to be fatal when used in combination with heroin. Though "speedballs" (when injected) or "moonrocks" (when smoked) are a popular mix of the two drugs among users, combinations of stimulants and depressants can have unpredictable and sometimes fatal results. In the United States in early 2006, a rash of deaths was attributed to either a combination of fentanyl and heroin, or pure fentanyl masquerading as heroin particularly in the Detroit Metro Area; one news report refers to the combination as 'laced heroin', though this is likely a generic rather than a specific term.^[34]

[edit] Harm reduction approaches to heroin

Proponents of the harm reduction philosophy seek to minimize the harms that arise from the recreational use of heroin. Safer means of taking the drug, such as smoking or nasal, oral and rectal insertion, are encouraged, due to injection having higher risks of overdose, infections and blood-borne viruses. Where the strength of the drug is unknown, users are encouraged to try a small amount first to gauge the strength, to minimize the risks of overdose. For the same reason, poly drug use (the use of two or more drugs at the same time) is discouraged. Users are also encouraged to not use heroin on their own, as others can assist in the event of an overdose. Heroin users who choose to inject should always use new needles, syringes, spoons/steri-cups and filters every time they inject and not share these with other users. Governments that support a harm reduction approach often run Needle & Syringe exchange programs, which supply new needles and syringes on a confidential basis, as well as education on proper filtering prior to injection, safer injection techniques, safe disposal of used injecting gear and other equipment used when preparing heroin for injection may also be supplied including citric acid sachets/vitamin C sachets, steri-cups, filters, alcohol pre-injection swabs, sterile water ampules and tourniquets (to stop use of shoe laces or belts).

[edit] Withdrawal

The withdrawal syndrome from heroin may begin within 6 to 24 hours of discontinuation of the drug; however, this time frame can fluctuate with the degree of tolerance as well as the amount of the last consumed dose. Symptoms may include: sweating, malaise, anxiety, depression, priapism, extra sensitivity of the genitals in females, general feeling of heaviness, cramp-like pains in the limbs, excessive yawning or sneezing, tears, rhinorrhea, sleep difficulties (insomnia), cold sweats, chills, severe muscle and bone aches; nausea and vomiting, diarrhea, cramps, and fever.^[35] Many users also complain of a painful condition, the so-called "itchy blood", which often results in compulsive scratching that causes bruises and sometimes ruptures the skin, leaving scabs. Abrupt termination of heroin use often causes muscle spasms in the legs (restless leg syndrome, (also known as "kicking the habit")). The intensity of the withdrawal syndrome is variable depending on the dosage of the drug used and the frequency of use. Very severe withdrawal can be precipitated by administering an opioid antagonist to a heroin addict.

Three general approaches are available to ease the physical part of opioid withdrawal. The first is to substitute a longer-acting opioid such as methadone or buprenorphine for heroin or occasionally another short-acting opioid and then slowly taper the dose.

In the second approach, benzodiazepines such as diazepam (Valium) may be recommended for opiate withdrawal especially if there is comorbid alcohol withdrawal. Benzodiazepines may temporarily ease the anxiety, muscle spasms, and insomnia associated with opioid withdrawal. The use of benzodiazepines must be carefully monitored because these drugs have a high risk of physical dependence as well as abuse potential and have little or no cross tolerance with opiates and thus are not generally recommended as a first line treatment strategy. Also, although very unpleasant, opioid withdrawal is seldom fatal, whereas complications related to withdrawal from benzodiazepines, barbiturates and alcohol withdrawal (such as psychosis, suicidal depression, epileptic seizures, cardiac arrest, and delirium tremens) can prove hazardous and are potentially life-threatening.

Many symptoms of opioid withdrawal are due to rebound hyperactivity of the sympathetic nervous system, which can be suppressed with clonidine (Catapres), a centrally-acting alpha-2 agonist primarily used to treat hypertension. Another drug sometimes used to relieve the "restless legs" symptom of withdrawal is baclofen, a muscle relaxant. Diarrhoea can likewise be treated with the peripherally active opioid drug loperamide.

Methadone is another μ-opioid agonist most often used to substitute for heroin in treatment for heroin addiction. Compared to heroin, methadone is well (but slowly) absorbed by the gastrointestinal tract and has a much longer duration of action of approximately 24 hours. Thus methadone maintenance avoids the rapid cycling between intoxication and withdrawal associated with heroin addiction. In this way, methadone has shown success as a substitute for heroin; despite bearing about the same addiction potential as heroin, it is recommended for those who have repeatedly failed to complete withdrawal or have recently relapsed. Patients properly stabilized on methadone display few subjective effects to the drug (i.e., it does not make them "high"), and are unable to obtain a "high" from other opioids except with very high doses. Methadone, since it is longer-acting, produces withdrawal symptoms that appear later than with heroin, but usually last considerably longer and can in some cases be more intense. Methadone withdrawal symptoms can potentially persist for over a month, compared to heroin where significant physical symptoms subside within 4 - 7 days.

Buprenorphine is another opioid that was recently licensed for opioid substitution treatment. As a μ-opioid receptor partial agonist, patients develop less tolerance to it than to heroin or methadone due to its partial activation of the opiate receptor. Patients are unable to obtain a "high" from other opioids during buprenorphine treatment except with very high doses. It also has less severe withdrawal symptoms than heroin or other full agonist opiates when discontinued abruptly, although the duration of the withdrawal syndrome is often longer than that seen with heroin. It is usually administered sublingually (dissolved under the tongue) every 24-48 hrs. Buprenorphine is also a κ opioid receptor antagonist, which led to speculation that the drug might have additional antidepressant effects; however, no significant difference was found in symptoms of depression between patients receiving buprenorphine and those receiving methadone.^[36]

Researchers at Johns Hopkins University have been testing a sustained-release "depot" form of buprenorphine that can relieve cravings and withdrawal symptoms for up to six weeks.^[37] A sustained-release formulation would allow for easier administration and adherence to treatment, and reduce the risk of diversion or misuse.

Three opioid antagonists are available: naloxone and the longer-acting naltrexone and nalmefene. These medications block the ability of heroin, as well as the other opioids to bind to the receptor site.

There is also a controversial treatment for heroin addiction based on an Iboga-derived African drug, ibogaine. Many people travel abroad for ibogaine treatments that generally interrupt substance use disorders for 3-6 months or more in up to 80% of patients.^[38]

[edit] Heroin prescription

The UK Department of Health's Rolleston Committee report in 1926 established the British approach to heroin prescription to users, which was maintained for the next forty years: dealers were prosecuted, but doctors could prescribe heroin to users when withdrawing from it would cause harm or severe distress to the patient. This "policing and prescribing" policy effectively controlled the perceived heroin problem in the UK until 1959 when the number of heroin addicts doubled every sixteenth month during a period of ten years, 1959-1968.^[39] The failure changed the attitudes; in 1964 only specialized clinics and selected approved doctors were allowed to prescribe heroin to users. The law was made more restrictive in 1968. Beginning in the 1970s, the emphasis shifted to abstinence and the use of methadone, until now only a small number of users in the UK are prescribed heroin.^[40]

In 1994 Switzerland began a trial heroin maintenance program for users that had failed multiple withdrawal programs. The aim of this program is to maintain the health of the user in order to avoid medical problems stemming from the use of illicit street heroin. Reducing drug-related crime and preventing overdoses were two other goals. The first trial in 1994 involved 340 users, although enrollment was later expanded to 1000 based on the apparent success of the program. Participants are allowed to inject heroin in specially designed pharmacies for 15 Swiss Francs per dose.^[41] A national referendum in November 2008 showed 68% of voters supported the plan,^[42] introducing heroin prescription into federal law. The trials before were based on time-limited executive ordinances.

The success of the Swiss trials led German, Dutch,^[43] and Canadian^[44] cities to try out their own heroin prescription programs.^[45] Some Australian cities (such as Sydney) have instituted legal heroin supervised injecting centers, in line with other wider harm minimization programs.

Starting in January 2009 Denmark is also going to prescribe heroin to a few addicts that have tried methadone and subutex without success.^[46]

[edit] Controversy

It has been claimed that sustained use of heroin for as little as three days can cause withdrawal symptoms to appear if use is stopped, and the myth that "just one shot will hook you for life" has been one of the many sensationalist claims made about the drug. A belief in its overwhelming ability to addict anyone who tries it is one of the main justifications for heroin's continuing prohibition. The truth is that true physical dependence on heroin demonstrated by genuine physical withdrawal symptoms upon discontinuation of consumption (as opposed to a mental or psychological craving to repeat the heroin experience) is not acquired any faster than with continuous use of any other opiate, normally between three to six weeks in an opiate naive person. Many times patients in UK hospitals are treated with diamorphine daily for many weeks following painful surgery without experiencing any withdrawal upon discontinuation of the drug.^[47][48]

[edit] Popular culture

This article contains too many minor or trivial fictional references. Mere trivia, or references unimportant to the overall plot of a work of fiction, should be deleted. See also what Wikipedia is not.

[edit] Literature

• Beat Generation author William S. Burroughs wrote about his experiences with heroin in numerous books, starting with the 1953 semi-autobiographical Junkie (aka Junky).
• The Basketball Diaries is a 1978 book written by American author and musician Jim Carroll. It is an edited collection of the diaries he kept between the ages of twelve and sixteen. Set in New York City, they detail his daily life, sexual experiences, high school basketball career, Cold War paranoia, the counterculture movement, and, especially, his addiction to heroin, which began when he was 13. The book was made into a film under the same name in 1995 starring Leonardo DiCaprio.
• Irvine Welsh's 1993 novel Trainspotting which was later made into a feature film under the same name explores the turbulent lives of an eccentric group of heroin users.
• Allen Hoey's 2006 novel, Chasing the Dragon, examines the use of heroin among jazz musicians in the 1950s.
• A 2007 book entitled The Heroin Diaries by author and musician Nikki Sixx from Mötley Crüe and Sixx:A.M. chronicles his heroin addiction in his diary between the years 1986-1987, as well as his chronic extreme hedonism, attitudes, drug use and his inevitable route to dying and coming back to life.
• A 2008 book entitled "The Death Proclamation of Generation X: A Self-Fulfilling Prophesy of Goth, Grunge and Heroin" by researcher Maxim W. Furek investigates the prominence of heroin in music, motion pictures and Generation X culture. Published by i-Universe. ISBN 978-0-595-46319-0

[edit] Musicians who have used, or written about, heroin use

• Jay-Z, in his song "I Know" from his 2007 American Gangster album wrote from the perspective of actually personifying the drug and how it interacts with and effects it's users and abusers minds. From the same album came the single "Blue Magic", who's name is a direct reference to the kind of heroin that Frank Lucas sold in the movie American Gangster, the CD even came in a package similar to the one Lucas' heroin was sold in.

• A number of songs by the Velvet Underground refer to heroin, including "I'm Waiting For The Man" and"Heroin". These are some of the first references in popular music to the drug.

• Kurt Cobain of Nirvana was heavily addicted to heroin. His autopsy showed that he had 3 times the lethal dosage of heroin and other substances before he died.

• Megadeth frontman Dave Mustaine is known for his past heroin drug abuse.

• Andrew Wood from grunge band Mother Love Bone died from heroin overdose before Mother Love Bone's first album was released.

• Alice in Chains frontman Layne Staley was also a well published heroin addict, right up to his death by overdose in April 2002. He wrote countless songs about his drug addiction including "God Smack", "Junkhead", and "Hate to Feel".

• Jazz artist Miles Davis was a heroin addict.

• John Lennon wrote the song "Cold Turkey" about his and Yoko Ono's attempts to get off the drug.

• David Bowie's first single "Space Oddity," was seemingly about his experience with heroin, as his 1980 single "Ashes to Ashes" included the lines that refer to Major Tom as "... a junkie/strung out on heaven's high/hitting an all-time low."^[49]

• The Rolling Stones' 1973 song "Coming Down Again" was written by Keith Richards about his experiences with heroin; "Before They Make Me Run" (1978) is about his views on overcoming his addiction.

• The Stranglers' single "Golden Brown", from the late 1970s, is believed by some to be about a batch of brown heroin from Afghanistan that arrived in the UK around that time.

• Bradley Nowell of Sublime wrote the song "Pool Shark", which deals with his heroin addiction.

• Dee Dee Ramone (aka Douglas Colvin) of the US punk band The Ramones used heroin and wrote the song "Chinese Rocks".

• The songs "Mr. Brownstone" and "Bad Obsession" by Guns N' Roses also deal with heroin.

• The Red Hot Chili Peppers have numerous drug references in their music, most famously "Under the Bridge", a song about Anthony Kiedis's heroin experience in the chicano-run areas of Los Angeles. "Knock Me Down" was about the band's first guitarist, Hillel Slovak who died after overdosing on a mix of cocaine and heroin.

• Black Sabbath wrote a song, "Hand of Doom", which talks about the negative effects of heroin.

• Nikki Sixx wrote a song about his heroin addiction, which is included on the 1987 Motley Crue album "Girls, Girls, Girls" titled "Dancing on Glass". Sixx also wrote the hit "Kickstart My Heart" which was written about a Heroin overdose by Sixx. Sixx also wrote "The Heroin Diaries".

• Suede recorded many songs about heroin. They have two songs which refer to lead singer Brett Anderson's addiction to the drug, and one simply called "Heroin", which features on their second LP Dog Man Star

• The Used song, "Let It Bleed" refers to frontman Bert McCracken's heroin addiction before the band started.

• 80's pop superstar Boy George used heroin. He also wrote and recorded a song of his experience with the drug titled "You Are My Heroin" in 1988.

• Rozz Williams' final album before his suicide, The Whorse's Mouth, dealt with his heroin addiction.^[50]

• Many songs by singer song writer Elliott Smith such as "A Fond Farewell", and "King's Crossing" refer to his addiction with heroin.

• Argentinian band Sumo's lead singer Luca Prodan, escaped from Europe to Argentina to get rid of his heroin addiction.

• Wil Francis, lead singer for the American post-hardcore band Aiden was addicted to heroin, and makes several references to his addiction in the album Nightmare Anatomy, including "Genetic Design for Dying".

• Industrial metal band Ministry's track Just One Fix deals with Al Jourgensen's heroin use.

• Philip Anselmo from Heavy Metal band Pantera overdosed on heroin after a show, inspiring the song "Death Rattle".

• Pete Townshend suffered from heroin addiction in the 1980s. There are several passing references to heroin in his solo work, including "your love is like heroin" and "his pride is just like heroin".

• Sid Vicious from the Sex Pistols died of a heroin overdose, and allegedly stabbed his girlfriend to death while both were strung out on heroin.

• The Gun Club, LA based punk-rock group released the song "She's Like Heroin To Me" on their first album Fire of Love in 1981

• The Brian Jonestown Massacre On their eight studio album And This Is Our Music two songs concern the use of heroin; "Prozac vs. Heroin" and "Prozac vs. Heroin Revisited"

[edit] Film

• Darren Aronosfky's 2000 film Requiem for a Dream depicts the lives of a group of heroin addicts and the devastating results of their addiction.

• The film Trainspotting, based on the book of the same name, revolves around a group of heroin users and the attempts of one of the group's efforts to quit.

• The film RENT (2005), based on the musical by Jonathan Larson, includes a character, mimi who struggles with a heroin addiction and has contracted AIDS from her usage.

• The film Candy starring Heath Ledger focused on a couple very much in love and destroyed by heroin addiction.

• Party Monster, a movie based on James St. James' true tales of New York City club kids in the late 1980s, shows an extreme use of heroin and other drugs such as ketamine (Special K) and cocaine.

• The Film "Gia" based on a true story of model Gia Carangi is about her addiction and use of heroin and how it affected her.

• The film "Christiane F." portraying the troubles of young heroin users in Berlin.

• The film "Things We Lost in the Fire", deals with Benicio del Toro's character's struggle to get clean.

• The film American Gangster is based on real life drug lord Frank Lucas who sold heroin.

• In the T.V. show Lost, Charlie Pace is a heroin addict. Also, Mr. Eko is hired to smuggle drugs out of Nigeria but the plane crashes on the island.

[edit] See also

Look up heroin in Wiktionary, the free dictionary.

• Alphamethylfentanyl another drug with the street name "China White"
• Morphine
• Opioids
• Black Tar Heroin
• Cheese (recreational drug)
• HIV in Yunnan
• Drugs and prostitution
• Ibogaine
• Monoacetylmorphine
• Dipropanoylmorphine
• Diacetyldihydromorphine
• Recreational drug use
• Psychoactive drug
• The Great Binge
• Opium
• Polish heroin
• Poppy
• Drug injection
• Illegal drug trade
• Illicit drug use in Australia
• Entomotoxicology

[edit] References

[edit] Literature

• Diary Of A Drug Fiend by Aleister Crowley (1922)
• Heroin (1998) ISBN 1-56838-153-0
• Heroin Century (2002) ISBN 0-415-27899-6
• This is Heroin (2002) ISBN 1-86074-424-9
• The Heroin User's Handbook by Francis Moraes (paperback 2004) ISBN 1-55950-216-9
• The Little Book of Heroin by Francis Moraes (paperback 2000) ISBN 0-914171-98-4
• Heroin: A True Story of Addiction, Hope and Triumph by Julie O'Toole (paperback 2005) ISBN 1-905379-01-3
• The Heroin Diaries: A Year in the Life of a Shattered Rockstar by Nikki Sixx (2007) ISBN 978-0743486-28-6
• Heroin: The Myths and the Facts by Richard Ashley (1972), St. Martin's Press, Library of Congress No. 72-89417
• "The Death Proclamation of Generation X: A Self-Fulfilling Prophesy of Goth, Grunge and Heroin" by Maxim W. Furek, M. (2008), i-Universe. ISBN 978-0-595-46319-0

[edit] External links

Wikimedia Commons has media related to: Heroin

• Border Stories: Heroin use and the AIDS epidemic in Tijuana, Mexico (VIDEO)
• Geopium: Geopolitics of Illicit Drugs in Asia, especially opium and heroin production and trafficking in and around Afghanistan and Burma (Articles and maps and French and English)
• Drugs Factfile what you really need to know
• The mismanagement of methadone
• Harrowing Heroin by Geoff Morton
• National Alliance of Advocates for Buprenorphine Treatment - non-profit education website for treatment of Heroin addiction
• NIDA InfoFacts on Heroin
• ONDCP Drug Facts
• United States Department of State fact sheet: anti-narcotics efforts in Pakistan - dated June 7, 2002
• BBC Article entitled 'When Heroin Was Legal'. References to the United Kingdom and the United States
• Harm reduction strategies in relation to heroin and other illicit drugs
• Heroin news page - Alcohol and Drugs History Society

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v • d • e Analgesic products (N02A, N02B) Opioids See also: Opioids template Opium & alkaloids thereof Codeine · Morphine · Opium · Laudanum · Paregoric Semi-synthetic opium derivatives Acetyldihydrocodeine · Benzylmorphine · Desomorphine · Dihydrocodeine · Dihydromorphine · Ethylmorphine · Diamorphine · Hydrocodone · Hydromorphinol · Hydromorphone · Nicocodeine · Nicodicodeine · Nicomorphine · Oxycodone · Oxymorphone · Dihydrocodeinone Synthetic opioids Alphaprodine · Anileridine · Buprenorphine · Butorphanol · Dextromoramide · Dextropropoxyphene · Dezocine · Fentanyl · Ketobemidone · Levorphanol · Methadone · Meptazinol · Nalbuphine · Pentazocine · Propoxyphene · Propiram · Pethidine · Phenazocine · Piminodine · Piritramide · Tapentadol · Tilidine · Tramadol · Pyrazolones Ampyrone/Aminophenazone · Metamizole · Phenazone Cannabinoids Ajulemic acid · AM404 · Cannabidiol · Cannabis · Nabilone · Tetrahydrocannabinol Anilides Paracetamol (acetaminophen) · Phenacetin · Propacetamol Non-steroidal anti-inflammatories See also: NSAIDs template Propionic acid class Fenoprofen · Flurbiprofen · Ibuprofen · Ketoprofen · Naproxen · Oxaprozin Oxicam class Meloxicam · Piroxicam Acetic acid class Diclofenac · Indometacin · Ketorolac · Nabumetone · Sulindac · Tolmetin COX-2 inhibitors Celecoxib · Rofecoxib · Valdecoxib · Parecoxib · Lumiracoxib Anthranilic acid (fenamate) class Meclofenamate · Mefenamic acid Salicylates Aspirin (Acetylsalicylic acid) · Benorylate · Diflunisal · Ethenzamide · Magnesium salicylate · Salicin · Salicylamide · Salsalate · Trisalate · Wintergreen (Methyl salicylate) Atypical, adjunct and potentiators, miscellaneous Bicifadine · Camphor · Clonidine · Cyclobenzaprine · Duloxetine · Flupirtine · Gabapentin · Glafenine · Menthol · Nefopam · Orphenadrine · Scopolamine · Tebanicline · Trazodone · Ziconotide

International Chemical Identifier
InChI=	1/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
InChIKey=	GVGLGOZIDCSQPN-PVHGPHFFBL
CASRN=	561-27-3
PIN=	diacetylmorphine