Heroin

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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 g/mol
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	<10 minutes [1]
Excretion	90% renal as glucuronides, rest biliary
Therapeutic considerations
Pregnancy cat.	Category X
Legal status	Prohibited (S9) (AU) Schedule I (CA) ? (UK) Schedule I (US)
Dependence Liability	Extremely High
Routes	Inhalation, Transmucosal, Intravenous, Oral, Intranasal, Rectal, Intramuscular
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Heroin, or diacetylmorphine (INN), also known as diamorphine (BAN), is a semi-synthetic opioid drug synthesized from morphine, a derivative of the opium poppy. It is the 3,6-diacetyl ester of morphine (di (two)-acetyl-morphine). The white crystalline form is commonly the hydrochloride salt diacetylmorphine hydrochloride, though often adulterated thus dulling the sheen and consistency from that to a matte white powder, which heroin freebase typically is.^[2]

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

Internationally, heroin is controlled under Schedules I and IV of the Single Convention on Narcotic Drugs.^[3] It is illegal to manufacture, possess, or sell diacetylmorphine without a license 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. It is available for prescription to long-term users in the Netherlands, United Kingdom, Switzerland, Germany and Denmark alongside psycho-social care,^[4][5] and a similar program is being campaigned for by liberal political parties in Norway.

Contents 1 Etymology 2 History 3 Pharmacology 4 Usage and effects 4.1 Medical use 4.2 Recreational use 4.3 Effects 5 Regulation 6 Price 7 Production and trafficking: The Golden Triangle 7.1 Manufacturing 7.2 History of heroin traffic 7.3 Trafficking 8 Risks of use 9 Harm reduction 10 Withdrawal 11 Heroin prescription for addicts 12 Popular culture 12.1 Literature 12.2 Musicians who have used heroin, or written about heroin use 12.3 Film and TV 13 See also 14 References 15 Literature 16 External links

Etymology

The German drug company Bayer named its new over the counter drug "Heroin" in 1895.^[6] The name was derived from the German word "heroisch" (heroic) due to its perceived "heroic" effects upon a user.^[6] However it was chiefly developed as a morphine substitute for cough suppressants that did not have morphine's addictive side-effects; morphine at the time was a popular recreational drug so Bayer wanted to find a similar but non-addictive substitute to market.^[7] However, contrary to Bayer's advertising as a "non-addictive morphine substitute," heroin would soon have one of the highest rates of dependence amongst its users.^[8]

History

The opium poppy was cultivated in lower Mesopotamia as long ago as 3400 BCE.^[9] 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. He had been experimenting with combining morphine with various acids. He boiled anhydrous morphine alkaloid with acetic anhydride 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. Pierce told 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°.[10]

”

Wright's invention 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 Aktiengesellschaft Farbenfabriken (today 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, pharmacologically similar to morphine but less potent and less addictive. Instead the experiment produced an acetylated form of morphine one and a half to two times more potent than morphine itself.

From 1898 through to 1910 diacetylmorphine was marketed under the name heroin as a non-addictive morphine substitute and cough suppressant. Bayer marketed heroin as a cure for morphine addiction before it was discovered that it rapidly metabolizes into morphine. As such, heroin is essentially a quicker acting form of morphine. The company was embarrassed by the new finding, which became a historic blunder for Bayer.^[11]

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, which allowed the drug to be prescribed and sold for medical purposes. In 1924 the United States Congress banned its sale, importation or manufacture. It is now a Schedule I substance, which makes it illegal for non-medical use in signatory nations of the Single Convention on Narcotic Drugs treaty, including the United States.

Later, 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.^[12]

Pharmacology

When taken orally, diacetylmorphine undergoes extensive first-pass metabolism via deacetylation, making it a prodrug for the systemic delivery of morphine.^[13] 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.^[14] 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.^[15] 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.^[16]

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.^[17] The contribution of these receptors to the overall pharmacology of heroin remains unknown.

A subclass of morphine derivatives, namely the 3,6 esters of morphine, with similar effects and uses includes the clinically-used strong analgesics nicomorphine (Vilan), and dipropanoylmorphine; there is also the latter's dihydromorphine analogue, diacetyldihydromorphine (Paralaudin).

Usage and effects

Worldwide, the UN estimates there are more than 50 million regular users of heroin, cocaine and synthetic drugs.^[18] Global users of heroin are estimated at between 15.16 million and 21.13 million people aged 15–64.^[19]

Medical use

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Under the name diamorphine, heroin is prescribed as a strong analgesic in the United Kingdom, where it is given via subcutaneous, intramuscular, intrathecal or intravenous route. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses. 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.^[20] Due to this, many hospitals changed to using morphine instead of diamorphine. Although there is no longer a problem with the manufacturing of heroin in the UK, many hospitals there have continued to use morphine.

Diamorphine continues 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. In the UK, it is a class A controlled drug. Registers of its use are required to be kept in hospitals.

Heroin is also used as a maintenance drug in the treatment of heroin addicts. Though this is somewhat controversial among proponents of a zero tolerance drug policy it has proven superior to methadone in improving the social and health situation of addicts.^[21] See: Heroin prescription for addicts

Recreational use

Diacetylmorphine is used as a recreational drug for the transcendent relaxation and intense euphoria it induces. Anthropologist Michael Agar once described heroin as "the perfect whatever drug."^[22] Tolerance quickly develops, and users need more of the drug to achieve the same effects. Its popularity with recreational drug users, compared to morphine, reportedly stems from its perceived different effects.^[23] 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. 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 recreational use, 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.^[24] 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.^[24]

One of the most common methods of illicit heroin use is via intravenous injection (colloquially termed "slamming" or "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.

Recreational users may also administer the drug through 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.^[25] 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. This method of administration is known as chasing the dragon (whereas smoking methamphetamine is known as "chasing the white dragon").

The onset of diacetylmorphine's effects depends upon the route 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.^[26] Intravenous injection provides the fastest and most intense rush^[27] within 7 to 8 seconds. Intra-muscular injection produces a relatively slow onset of 5 to 8 minutes. Snorting or smoking reaches peak effects within 10 to 15 minutes.^[28] If taken orally, the effects take approximately half an hour to set in, with an absence of a rush.

The diacetylmorphine dose used for recreational purposes is dependant on the frequency and level of use. A first-time user may ingest between 5 and 20 mg of diacetylmorphine, while an addict may require several hundred mg per day.^[29]

Large doses of heroin 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 heroin death was an accident, suicide or murder. Examples include the overdose deaths of Sid Vicious, Janis Joplin, Tim Buckley, Layne Staley, Bradley Nowell, Ted Binion, and River Phoenix.^[30]

Effects

Central nervous system:

• Drowsiness
• Disorientation
• Delirium

Neurological:

• Analgesia
• Tolerance
• Addiction (Physical Dependence)

Psychological:

• Addiction (Psychological Dependence)
• Anxiolysis
• Confusion
• Euphoria
• Somnolence

Cardiovascular & Respiratory:

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

Gastrointestinal:

• Nausea
• Vomiting (protracted)
• Constipation
• Dyspepsia

Musculoskeletal:

• Analgesia
• Ataxia
• Muscle spasticity

Skin:

• Itching
• Flushing/Rash

Miscellaneous:

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

Recreational uses: Euphoria Relaxation Medicinal uses: Powerful analgesic Cough suppressant anti-diarrheal

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

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.

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 €35-40 per gram. The price of white heroin is reported only by a few European countries and ranged between €27 and €110 per gram.^[33]

The United Nations Office on Drugs and Crime claims in its 2008 World Drug Report that typical US retail prices are US$172 per gram.^[34]

Production and trafficking: The Golden Triangle

Manufacturing

Heroin, also known as diacetyl morphine is produced from acetylation of morphine derived from natural opium sources. Numerous mechanical and chemical means are used to purify the final product. The final products have different appearance depending on purity and have different names.^[35]

History of heroin traffic

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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. The 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. Japan's war with China had cut the normal distribution routes for heroin and the war had generally disrupted the movement of opium.

After World War II, the Mafia took advantage of the weakness of the postwar Italian government and set up heroin labs in Sicily. The Mafia took advantage of Sicily's location along the historic route opium took westward into Europe and the United States.^[36]

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 recreational use 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 (formerly Burma), the heartland of the Golden Triangle remained the second largest producer of heroin, after Afghanistan.^[37]

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.^[37] 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.

Trafficking

See also: Opium#Modern production and usage

Traffic is heavy worldwide, with the biggest producer being Afghanistan.^[38] According to U.N. sponsored survey,^[39] as of 2004^[update], Afghanistan accounted for production of 87 percent of the world's heroin.^[40] Afghan opium kills 100,000 people every year worldwide.^[41]

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.^[42] Opium production in that country has increased rapidly since, reaching an all-time high in 2006. War in Afghanistan once again appeared as a facilitator of the trade.^[43] Some 3.3 million Afghans are involved in producing opium.^[44]

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 Southeast 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.

Risks of use

• 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)^[45]

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.

Anthropologists Philippe Bourgois and Jeff Schonberg, who did a decade of field work among homeless heroin and crack addicts in San Francisco, reported that the African-American addicts they observed were more inclined to "direct deposit" heroin into a vein, rather than "skin-popping" their injections. (Skin-popping was a far more widespread practice among the white addicts: "By the midpoint of our fieldwork, most of the whites had given up searching for operable veins and skin-popped. They sank their needles perfunctorily, often through their clothing, into their fatty tissue.") Bourgois and Schonberg describes how the cultural difference between the African-Americans and the whites leads to this contrasting behavior, and also points out that the two different ways to inject heroin comes with different health risks. Skin-popping more often results in abscesses, and direct injection more often leads to fatal overdose and also to hepatitis C and HIV infection.^[46]

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.^[47] 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.^[48] 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.^[49]

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.^[50]

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.^[51][52][53] Symptoms include slurred speech and difficulty walking.

Cocaine is sometimes used in combination with heroin, and is referred to as a speedball when injected or moonrocks when smoked together. Cocaine acts as a stimulant, whereas heroin acts as a depressant. Coadministration provides an intense rush of euphoria with a high that combines both effects of the drugs, while excluding the negative effects, such as anxiety and sedation. The effects of cocaine wear off far more quickly than heroin, thus if an overdose of heroin was used to compensate for cocaine, the end result is fatal respiratory depression.

Harm reduction

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 usually fund 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).

Another harm reduction measure employed for example in Switzerland and Germany are safe injection sites where users can inject heroin and cocaine under the supervision of medically trained staff. Those establishments also often include a cafeteria and a designated area where the sale and acquisition of small amounts of drugs among users is tolerated. Safe injection sites are low threshold and allow social services to approach problem users that would otherwise be hard to reach.^[54]

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.^[55]

Heroin prescription for addicts

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 40 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 16th month during a period of ten years, 1959–1968.^[56] 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.^[57]

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 to avoid medical problems stemming from 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 day.^[58] A national referendum in November 2008 showed 68% of voters supported the plan,^[59] 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,^[60] and Canadian^[61] cities to try out their own heroin prescription programs.^[62] Some Australian cities (such as Sydney) have instituted legal heroin supervised injecting centers, in line with other wider harm minimization programs.

Since January 2009 Denmark has prescribed heroin to a few addicts that have tried methadone and subutex without success.^[63] Beginning in February 2010, addicts in Copenhagen and Odense will be eligible to receive free heroin. Later in 2010 other cities including Århus and Esbjerg will join the scheme. In total, around 230 addicts will be able to receive free heroin.^[64] However, Danish addicts will only be able to inject heroin according to the policy set by Danish National Board of Health.^[65] Of the estimated 1500 drugs users who does not benefit from the current oral substitution treatment, approximately 900 will not be in the target group for treatment with injectable heroin, either because of "massive multiple drug abuse of non-opioids" or "not wanting treatment with injectable heroin".^[66]

In July 2009, the German Bundestag passed a law allowing heroin prescription as a standard treatment for addicts; while heroin prescription was started in 2002, it was only authorized as a large-scale trial.^[67]

Popular culture

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Literature

• In the 1926 novel, The Murder of Roger Ackroyd, there is a discussion between the book’s protagonist, Hercule Poirot, and the book’s narrator, Dr. James Sheppard, regarding a discovery the former made in a summer house on the estate where the novel’s titular character was murdered. In Chapter 13, “The Goose Quill,” Poirot discovers a goose quill used by addicts to carry “snow,” as the powdered form of heroin was then known. This clue is considered integral to solving the murder.

“Yes, heroin ‘snow.’ Drug-takers carry it like this, and sniff it up the nose.”

“Diamorphine hydrochloride,” I murmured mechanically.

“This method of taking the drug is very common on the other side. Another proof, if we wanted one, that the man come from Canada or the States.”^[68]

• 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)

Musicians who have used heroin, or written about heroin use

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• Nikki Sixx of Mötley Crüe released diaries from his time as a heroin addict named The Heroin Diaries: A Year in the Life of a Shattered Rock Star. An album was also produced based on the book.

• Kurt Cobain (front man of the grunge band Nirvana) was addicted to heroin for a stomach problem: he said he could not get any relief from any other substance. He allegedly committed suicide after taking heroin.

• Jim Morrison reportedly died of an overdose of heroin in a bathtub in Paris.

• The Velvet Underground song "Heroin" (from their first album The Velvet Underground and Nico) describes the use and effects of the drug, with Lou Reed singing from the perspective of a heroin addict, describing his thoughts and feelings while under the effects of the drug, while the music (led by a dissonant viola and guitar strums) is played to resemble the effects of heroin use (with rushed and calm parts interchanging). The song was ranked #448 on Rolling Stone Magazine's list of the 500 Greatest Songs of All Time. Another famous song from the album, "I'm Waiting for the Man", tells the story of a New Yorker waiting for his drug dealer, describing the city environment, and then buying and using the heroin, only to conclude singing "until tomorrow, but it's just another time".

• Neil Young wrote a song called "The Needle and the Damage Done" about heroin. The song reflected on the musicians he knew that took heroin and died from it.

• Pete Doherty, former Libertines frontman and current Babyshambles singer, has had a long-standing battle with heroin addiction.

• Led Zeppelin guitar player Jimmy Page struggled with heroin from 1975 to the early 1980s. The heroin had very serious effects on him, including hampering his guitar playing skills, and making him ultra-thin in the early 80's.

• 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."^[69]

• Megadeth's song from Megadeth's Album Youthanasia - Addicted to Chaos, is influenced by Dave Mustaine's use of heroin previously.

• Rozz Williams's final album before his suicide, The Whorse's Mouth, dealt with his heroin addiction.^[70]

• 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.^[71]

• Dee Dee Ramone of punk rock band The Ramones was addicted to heroin throughout most of his career. After leaving the band in 1992, he seemed to give up the substance. However, he was found dead from a heroin overdose in 2002.

• Hillel Slovak, founding member of the Red Hot Chili Peppers, died of a 'speedball' overdose, which includes both cocaine and heroin. Together with band member Anthony Kiedis, he battled a heroin addiction prior to his death.

• Anthony Kiedis, also a founding member of the Red Hot Chili Peppers, wrote about his heroin addiction in his autobiography, Scar Tissue.

• Layne Staley, frontman of Alice in Chains, was addicted to heroin and died of a 'speedball' overdose.

• Brad Nowell died of a heroin overdose shortly before Sublime's first major label album came out.

• Slash (guitarist for Guns N' Roses) documents his extensive heroin use in his self-titled autobiography.

• B.G. (rapper from New Orleans) raps about his previous addiction to heroin (via injection) in numerous songs.

• Etta James stated in her autobiography that she had many troubles with heroin addiction in the 1970s and 80s, admitting she was often in rehabilitation centers.

• Jerry Garcia (guitarist for the Grateful Dead) was a user of heroin for many years. He died in a rehabilitation facility while trying to get help for his heroin addiction.

• Phil Anselmo of Pantera was reported to have been addicted to Heroin up until the early 2000s.

• GG Allin, cult punk rock singer, was addicted to heroin and died of an accidental overdose in 1993, only six days after leaving prison and three days after attending the premier of the film, Hated.

• Bad Religion bassist, Jay Bentley was a heroin addict during the late 80's/early 90's. Bad Religion guitarist, Brett Gurewitz was also known for "experimenting" with heroin. Both entered rehab in the mid 90's and both are currently off drugs.

• NOFX drummer, Erik Sandin was a heroin addict from the 80's to the early 90's. The band told him if he didn't quit doing heroin, they wouldn't allow him to play on their new album. He quit taking heroin and since then has been completely sober and has been NOFX's drummer since that period.

Film and TV

• In 1916's short comedy The Mystery of the Leaping Fish (a parody of a coke-shooting Sherlock Holmes, played by Douglas Fairbanks), discovers a contraband container of opium (which he eagerly tastes).

• The first serious film drama about heroin addiction by a major studio was Otto Preminger's The Man with the Golden Arm, released in 1955. This tells the story of a heroin addict (played by Frank Sinatra) who gets clean while in prison but struggles to stay that way in the outside world. The film was nominated for three Academy Awards, including Sinatra for Best Actor in a Leading Role. The movie also sparked a change in the Hollywood Production Code, allowing motion pictures more freedom to explore hitherto taboo subjects such drug abuse.

• Quentin Tarantino's 1994 film Pulp Fiction fully depicts the steps of heroin injection by Vincent Vega (John Travolta), and subsequent near-fatal overdose by Mia Wallace (Uma Thurman) via snorting.

• Darren Aronosfky's 2000 film Requiem for a Dream, based on the book of the same name, 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 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.^[72]

• The film "Christiane F." portrays 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.^[73]

• 1971's The Panic In Needle Park starring Al Pacino revolves around Pacino's character and his girlfriend's addictions to heroin and the repercussions of it. The film features graphic scenes of users injecting the drug.

• Season 3 of the TV series 24 depicts Kiefer Sutherland starring as Jack Bauer struggling with a heroin addiction.

See also

Look up heroin in Wiktionary, the free dictionary.

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

v • d • e Recreational drug use Major Recreational Drugs Cannabinoids THC (Cannabis · Hashish · Hash oil) Depressants Barbiturates · Benzodiazepines · Ethanol (Alcoholic beverages) · GHB · Nonbenzodiazepines · Kava Entactogens MDA · MDMA (Ecstasy) Hallucinogens Psychedelics Bufotenin (Yopo · Vilca · Psychoactive toads) · DMT (Ayahuasca) · LSD-25 · Mescaline (Peyote · San Pedro · Peruvian Torch) · Psilocybin & Psilocin (Psilocybin mushrooms) Dissociatives DXM · Inhalants (Nitrous oxide) · Ketamine · PCP · Salvinorin A (Salvia divinorum) Deliriants Datura · Deadly Nightshade · Henbane · Mandrake Opioids Codeine · Diacetylmorphine (heroin) · Hydrocodone · Morphine (Opium) · Oxycodone · Kratom Stimulants Amphetamine · Arecoline (Areca) · Betel · Caffeine (Coffee - Tea) · Cathinone (Khat) · Cocaine (Coca) · Ephedrine (Ephedra) · Methamphetamine · Methylphenidate · Nicotine (Tobacco) · Theobromine (Cocoa) Culture and Related Topics Cannabis 420 · Stoner Film · Spiritual Use of Cannabis · Medical Cannabis · Cannabis Cultivation · Cannabis smoking Psychedelic Art · Drug · Experience · Literature · Music Other Counterculture of the 1960s · Club Drug · Dance Party · Drug Tourism · Drug Paraphernalia · Hippie · Party and Play · Poly Drug Use · Rave · Sex and Drugs Spiritual use of drugs Problems with Drug Use Abuse · Addiction (Prevention · Rehabilitation · Responsible Use) · Illegal Trade · Overdose Legality of Drug Use International 1961 Narcotic Drugs · 1971 Psychotropic Substances · 1988 Drug Trafficking State Level Drug Policy (Prohibition · Decriminalization) · Policy Reform (Liberalization · Harm Reduction · Demand Reduction) Other Designer Drug · Drug Possession · Drug Test · Hard and Soft Drugs · Narc · War on Drugs Lists of Countries by... Alcohol Consumed · Cannabis Legality (Annual Use · Lifetime Use) · Cocaine Use · Opiate Use · Tobacco Smoked

References

Literature

• Diary Of A Drug Fiend by Aleister Crowley (1922)
• Junkie (novel) by William S. Burroughs (1953) ISBN 0142003166
• 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
• Seeds of Terror: How Heroin is Bankrolling the Taliban and Al Qaeda, by Gretchen Peters, publ. Thomas Dunne Books (2009)

External links

Wikimedia Commons has media related to: Heroin

• UNODC - United Nations Office on Drugs and Crime - Afghan Opium Survey 2009
• 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

v • d • e Opioids (N02A) Opium and Poppy straw derivatives Crude opiate extracts Compote/Kompot/Polish heroin · Diascordium · B & O Supprettes · Dover's powder · Laudanum · Mithridate · Opium · Paregoric · Poppy straw concentrate · Poppy tea · Smoking Opium · Theriac Natural Opiates Opium Alkaloids see also: Components of Opium Codeine · Morphine · Oripavine · Pseudomorphine · Thebaine Alkaloid Salts Mixtures Pantopon · Papaveretum (Omnopon) · Tetrapon Semisynthetics Morphine Family 14-Hydroxymorphine · 14β-Hydroxymorphine · 14β-Hydroxymorphone · 2,4-Dinitrophenylmorphine · 6-Methyldihydromorphine · 6-Methylenedihydrodesoxymorphine · 6-Acetyldihydromorphine/6-Monoacetyldihydromorphine · Acetyldihydromorphine · Azidomorphine · Chlornaltrexamine · Chloromorphide · Dihydrodesoxymorphine (Desomorphine) · Dihydromorphine · Ethyldihydromorphine · Hydromorphinol · Methyldesorphine · N-Phenethylnormorphine · Pseudomorphine 3,6 Diesters of Morphine Acetylpropionylmorphine · Diacetyldihydromorphine (Dihydroheroin) · Dibenzoylmorphine · Dipropanoylmorphine · Heroin (Diacetylmorphine) · Heroin-7,8-Oxide · Nicomorphine Codeine-Dionine Family 14-Hydroxydihydrocodeine · Acetylcodeine · Benzylmorphine · Codeine methylbromide · Desocodeine · Methyldihydromorphine (Dihydroheterocodeine) · Ethylmorphine (Dionine) · Heterocodeine · Isocodeine · Morpholinylethylmorphine (Pholcodine) · Myrophine · Nalodeine · Transisocodeine Morphinones 14-Ethoxymetopon · 14-Methoxymetopon · 14β-Hydroxymorphone · 14-O-Methyloxymorphone · 14-Phenylpropoxymetopon · 7-Spiroindanyloxymorphone · 8,14-Dihydroxydihydromorphinone · Acetylmorphone · Ethyldihydromorphinone · Hydromorphinone · Hydromorphone · Hydroxycodeine · Methyldihydromorphinone · Metopon · Morphinol · Morphinone · N-Phenethyl-14-ethoxymetopon · Oxymorphol · Oxymorphone · Pentamorphone · Semorphone Codeinones 1-carboxy-14-hydroxydihydrocodeinone · 1-carbethoxy-14-hydroxydihydrocodeinone · Thebacon (Acetyldihydrocodeinone / Dihydrocodeinone enol acetate) · Codeinone · Codorphone · Codoxime · Hydrocodone · Monodihydrocodeineone · Oxycodone Dihydrocodeine Series 14-hydroxydihydrocodeine · Acetyldihydrocodeine · Dihydrocodeine · Dihydrodesoxycodeine/Desocodeine · Dihydroisocodeine · Nicocodeine · Nicodicodeine Nitrogen Morphine Derivatives Codeine-N-Oxide · Heroin-N-Oxide · Hydromorphone-N-Oxide · Morphine-N-Oxide Hydrazones Hydromorphazone · Morphazone · Oxymorphazone  Others α-chlorocodide · Pholcodine Active Opiate Metabolites Codeine-N-Oxide (Genocodeine) · Dihydromorphine-6-glucuronide · Hydromorphone-N-Oxide · Heroin-7,8-Oxide · Morphine-6-glucuronide · 6-Acetylmorphine · Morphine-N-Oxide (Genomorphine) · Naltrexol · Norcodeine · Normorphine Morphinans Morphinan Series 4-chlorophenylpyridomorphinan · Cyclorphan · Dextro-3-hydroxy-N-allylmorphinan · Dimemorfan · Levargorphan · Levallorphan · Levorphanol · Levorphan · Levophenacylmorphan · Levomethorphan · Norlevorphanol · N-Methylmorphinan · Oxilorphan · Phenomorphan · Methorphan / Racemethorphan · Morphanol / Racemorphanol · Ro4-1539 · Stephodeline · Xorphanol Others 1-Nitroaknadinine · 14-episinomenine · 5,6-Dihydronorsalutaridine · 6-Ketonalbuphine · Aknadinine · Butorphanol · Cephakicine · Cephasamine · Cyprodime · Drotebanol · Fenfangjine G · Nalbuphine · Sinococuline · Sinomenine (Cocculine) · Tannagine Benzomorphans 5,9-DEHB · Alazocine · Anazocine · Bremazocine · Cogazocine · Cyclazocine · Dezocine · Eptazocine · Etazocine · Ethylketocyclazocine · Fluorophen · Ketazocine · Metazocine · Pentazocine · Phenazocine · Quadazocine · Thiazocine · Tonazocine · Volazocine · Zenazocine 4-Phenylpiperidines Pethidines (Meperidines) Allylnorpethidine · Anileridine · Benzethidine · Carperidine · Difenoxin · Diphenoxylate · Etoxeridine (Carbetidine) · Furethidine · Hydroxypethidine (Bemidone) · Hydroxymethoxypethidine · Morpheridine · Oxpheneridine (Carbamethidine) · Meperidine-N-Oxide · Pethidine (Meperidine) · Pethidine Intermediate A · Pethidine Intermediate B (Norpethidine) · Pethidine Intermediate C (Pethidinic Acid) · Pheneridine · Phenoperidine · Piminodine · Properidine (Ipropethidine) · Sameridine Prodines Allylprodine · Isopromedol · Meprodine (α-meprodine / β-meprodine) · MPPP (Desmethylprodine) · PEPAP · Prodine (α-prodine / β-prodine) · Prosidol · Trimeperidine (Promedol) Ketobemidones Acetoxyketobemidone · Droxypropine · Ketobemidone · Methylketobemidone · Propylketobemidone Others Alvimopan · Loperamide · Picenadol Open Chain Opioids Amidones Dextromethadone · Dextroisomethadone · Dipipanone · Hexalgon (Norpipanone) · Isomethadone · Levoisomethadone · Levomethadone · Methadone · Methadone intermediate · Normethadone · Norpipanone · Phenadoxone (Heptazone) · Pipidone Methadols Dimepheptanol (Racemethadol) · Levacetylmethadol · Noracetylmethadol Moramides Dextromoramide · Levomoramide · Moramide intermediate · Racemoramide Thiambutenes Diethylthiambutene · Dimethylthiambutene · Ethylmethylthiambutene · Piperidylthiambutene · Pyrrolidinylthiambutene · Thiambutene · Tipepidine Phenalkoxams Dextropropoxyphene (Propoxyphene) · Dimenoxadol · Dioxaphetyl Butyrate · Levopropoxyphene · Norpropoxyphene Ampromides Diampromide · Phenampromide · Propiram Others IC-26 · Isoaminile · Lefetamine · R-4066 Anilidopiperidines 3-Allylfentanyl · 3-Methylfentanyl · 3-Methylthiofentanyl · Alfentanil · α-methylacetylfentanyl · α-methylfentanyl · α-methylthiofentanyl · Benzylfentanyl · β-hydroxyfentanyl · β-hydroxythiofentanyl · β-methylfentanyl · Brifentanil · Carfentanil · Fentanyl · Lofentanil · Mirfentanil · Ocfentanil · Ohmefentanyl · Parafluorofentanyl · Phenaridine · Remifentanil · Sufentanil · Thenylfentanyl · Thiofentanyl · Trefentanil Oripavine derivatives 6,14-Endoethenotetrahydrooripavine · 7-PET · Acetorphine · Alletorphine · BU-48 · Buprenorphine · Butorphine · Cyprenorphine · Dihydroetorphine · Diprenorphine (M5050) · Etorphine · 18,19-Dehydrobuprenorphine (HS-599) · N-cyclopropylmethyl-noretorphine · Nepenthone · Norbuprenorphine · Thevinone · Thienorphine Phenazepines Ethoheptazine · Meptazinol · Metheptazine · Metethoheptazine · Proheptazine Pirinitramides Bezitramide · Piritramide Benzimidazoles Clonitazene · Etonitazene · Nitazene Indoles 18-MC · 7-Acetoxymitragynine · 7-Hydroxymitragynine · Akuammidine · Akuammine · Eseroline · Hodgkinsine · Ibogaine · Mitragynine · Noribogaine · Pericine · ψ-Akuammigine Diphenylmethylpiperazines BW373U86 · DPI-221 · DPI-287 · DPI-3290 · SNC-80 Opioid peptides see also: The Opioid Peptides Casomorphin · DADLE · DALDA · DAMGO · Dermenkephalin · Dermorphin · Deltorphin · DPDPE · Dynorphin · Endomorphin · Endorphin · Enkephalin · Gliadorphin · Morphiceptin · Nociceptin · Octreotide · Opiorphin · Rubiscolin · TRIMU 5 Others 3-(3-Methoxyphenyl)-3-ethoxycarbonyltropane · Azaprocin · BDPC · Bisnortilidine · BRL-52537 · Bromadoline • C-8813 · Ciramadol · Enadoline · Faxeladol · Herkinorin · J-113,397 · JTC-801 · Methopholine · NNC 63-0532 · Nortilidine · O-Desmethyltramadol · Phenadone · Prodilidine · Profadol · Ro64-6198 · Salvinorin A · SB-612,111 · SC-17599 · RWJ-394,674 · TAN-67 · Tapentadol · Tecodine · Tifluadom · Tilidine · Tramadol · Trimebutine · Viminol · W-18 · Opioid Antagonists & Inverse-Agonists 5'-Guanidinonaltrindole · β-Funaltrexamine · 6β-Naltrexol · Alvimopan · Amiphenazole · Binaltorphimine · Chlornaltrexamine · Clocinnamox · Cyclazocine · Cyprodime · Diprenorphine (M5050) · Fedotozine · JDTic · Levallorphan · Methocinnamox · Methylnaltrexone · Nalfurafine · Nalmefene · Nalmexone · Naloxazone · Naloxonazine · Naloxone · Naloxone benzoylhydrazone · Nalorphine · Naltrexone · Naltriben · Naltrindole · Norbinaltorphimine · Oxilorphan · S-allyl-3-hydroxy-17-thioniamorphinan (SAHTM)

v • d • e Analgesics (N02A, N02B) Opioids See also: Opioids template Opium & alkaloids thereof Codeine · Morphine · Opium · Laudanum · Paregoric Semi-synthetic opium derivatives Acetyldihydrocodeine · Benzylmorphine · Buprenorphine · Desomorphine · Dihydrocodeine · Dihydromorphine · Ethylmorphine · Diamorphine · Hydrocodone · Hydromorphinol · Hydromorphone · Nicocodeine · Nicodicodeine · Nicomorphine · Oxycodone · Oxymorphone Synthetic opioids Alphaprodine · Anileridine · 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 · Propyphenazone Cannabinoids Ajulemic acid · AM404 · Cannabidiol · Cannabis · Nabilone · Nabiximols · 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 Befiradol · Bicifadine · Camphor · Clonidine · Cyclobenzaprine · Duloxetine · Esreboxetine · Flupirtine · Gabapentin · Glafenine · Hydroxyzine · Menthol · Nefopam · Orphenadrine · Pregabalin · Scopolamine · Tebanicline · Trazodone · Ziconotide CNS: anat/physio/dev, noncongen/congen/neoplasia, symptoms+signs/eponymous, proc, medsN (1A/2AB/2C/3/4/7A/7B/7C/7D)

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