Heroin

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Diacetylmorphine
IUPAC name: (5α,6α)-7,8-didehydro-4,5-epoxy- 17-methylmorphinan-3,6-diol diacetate (ester)
CAS number 561-27-3	ATC code N02AA09
Chemical formula	C21H23NO5
Molecular weight	369.42
Bioavailability	?
Metabolism	?
Elimination half life	3 minutes
Excretion	?
Pregnancy category	?
Legal status	Schedule I (USA)
Delivery	Vaporized, Insufflated, Injected, Taken Orally

Indicated for: Relief of extreme pain Recreational uses: Euphoria Relaxation Unethical uses: ? Other uses: Pain Relief Cough Suppressant

Contraindications: Alcohol Barbituates Stimulants Other Opioids

Side effects: Severe: Atypical sensations: ? Cardiovascular: Lowered heart rate Ear, nose, and throat: ? Endocrinal: ? Eye: Pupil constriction Gastrointestinal: Nausea Constipation Hematological: ? Musculoskeletal: ? Neurological: Analgesia Psychological: Confusion Euphoria Sedation Respiratory: Slow respiration Shallow respiration Respiratory arrest Skin: Itchiness Urogenital and reproductive: ? Miscellaneous: ?

Heroin or diamorphine (INN) (colloquially referred to as junk, babania, horse, golden brown, smack, black tar, H, big H, lady H, dope, skag, juice, diesel, etc.) is an alkaloid opioid. Heroin is the 3,6-diacetyl derivative of morphine (hence diacetylmorphine) and is synthesised from it by acetylation. The white crystalline form is commonly the hydrochloride salt, diamorphine hydrochloride. It is highly addictive. Heroin is controlled under Schedules I and IV of the Single Convention on Narcotic Drugs[1] (http://www.incb.org/pdf/e/list/yellow.pdf).

Contents

1 History 2 Usage and effects 3 Production and trafficking 4 Direct short and long term effects of heroin use 5 General risks from illicit use 6 Withdrawal symptoms 7 Drug interactions 8 Cultural influences 8.1 Novels 8.2 Factual accounts 8.3 Films 8.4 Songs 8.5 Musicals 9 See also 10 External links 11 Books

History

Heroin was first synthesised in 1874 by C.R.A. Wright, a British chemist working at St. Mary's Hospital Medical School, London. 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. We now call it diacetylmorphine. The compound was sent to F.M. Pierce of Owens College, Manchester, for analysis. He 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 dilated, 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° [2] (http://adhpage.dilaudid.net/heroin.html)

Heinrich Dreser, of Bayer in Elberfeld, Germany, noticed that diacetylmorphine was more potent than morphine. Bayer registered Heroin (meaning 'heroic treatment' from the German word heroisch) as a trademark. From 1898 through to 1910 it was marketed as a non-addictive morphine substitute and cough medicine for children. As with Aspirin, Bayer lost some of its trademark rights to Heroin following World War I.

In 1914 the Harrison Narcotics Tax Act made it illegal to manufacture or possess heroin in the United States.

Usage and effects

Heroin is a μ-opioid (mu-opioid) agonist. Like all drugs of its class, it binds to and activates μ-opioid receptors found in the brain, spinal cord and gut. As a medicine, it is administered usually in the form of its hydrochloride as an analgesic for severe pain. It is illegal even for this purpose in the United States, but it is legally used by cancer patients in the United Kingdom and other countries.

Heroin is also widely and illicitly used as a powerful and addictive drug producing intense euphoria, which often disappears with increasing tolerance. Although many other μ-opioid agonists (e.g., morphine) can produce essentially the same effects, it is thought that heroin's popularity with recreational users comes from its especially rapid onset. This in turn comes from its high lipid solubility provided by the two acetyl groups, resulting in a very rapid penetration of the blood-brain barrier after nasal inhalation or intravenous injection. Once in the brain, heroin is rapidly metabolized into morphine by removal of the acetyl groups.

Methadone is another μ-opioid agonist often used to substitute for heroin in treatment for heroin addiction. Compared to heroin, methadone is well (but slowly) absorbed orally and has a much longer duration of action. Thus methadone maintenance avoids the rapid cycling between intoxication and withdrawal associated with heroin addiction. Also, by keeping the addict physically tolerant to opioids, methadone effectively blocks the euphoric effects of heroin. In this way, methadone has shown some success as a 'less harmful substitute'; it is in fact the single most effective treatment known for opioid addiction, and is recommended for those who have repeatedly failed complete detoxification.

Heroin is similar in effects on brain chemistry to endorphins, the natural (endogenous) opioids of the body and less potent. It competes with the endorphins for the specialized endorphine (opioid) receptors found on the surfaces of some body cells. The body responds by reducing (or even stopping) production of endorphins when heroin is consumed. Endorphins are regularly released in the brain and nerves and attenuate pain. Their other functions, if any, are still obscure. The reduced endorphin production in heroin users makes them dependent on the heroin since a lack of either endorphins or heroin results in the extreme symptoms including pain (even in the absence of physical trauma). This is what causes the withdrawal symptoms in heroin addicts as the body takes some time to restore endorphin production.

The University of Chicago undertook preliminary development of a heroin vaccine in monkeys during the 1970s, but it was abandoned. There were two main reasons for this. Firstly, when immunised monkeys had an increase in dose of x16, their antibodies became saturated and the monkey had the same effect from heroin as non-immunised monkeys. Secondly, until they reached the x16 point immunised monkeys would substitute other drugs to get a heroin-like effect. These factors suggested that immunised human addicts would simply either take massive quantities of heroin, or switch to other hard drugs.

Production and trafficking

Heroin is a controlled substance produced for the market through opium refinement processes. Traffic is heavy worldwide, with the biggest producer being Afghanistan, which after a ban on poppy growing by the Taliban in 2001 dropped its production by 95% but revived it to record numbers following the U.S. military occupation and fall of the Taliban government. Currently, an estimated 86% of the global heroin supply is cultivated in Afghanistan, up from 75% in 2003 according to the UN Office of Drugs and Crime. The estimated value of the 2003 harvest is 2.8 billion U.S. dollars. Some observers, particularly political conservatives in the United States, have accused China of being a leading producer of heroin, but evidence in support of this is questionable. Heroin is one of the most profitable illicit drugs since it is compact and easily concealed. At present, opium poppies are mostly grown in the Middle East, Pakistan, and Afghanistan, and in Asia, especially in the region known as the Golden Triangle straddling Myanmar, Thailand, Vietnam, Laos and Yunnan province in 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.

Direct short and long term effects of heroin use

• mental confusion
• euphoria
• slow and shallow respiration leading to respiratory arrest
• nausea and vomiting
• constipation
• death, caused either directly via overdose, or through diseases transmitted intravenously via contaminated injection needles (Some countries have instituted programs to supply clean needles to addicts to reduce these risks, but others — including the United States — have resisted such efforts.)

General risks from illicit use

• HIV/AIDS and hepatitis infections from shared needles
• overdose, sometimes fatal
• long-term criminal involvement to support heroin habits
• malnourishment
• bacterial or fungal endocarditis
• skin conditions from constant injecting, often with poor technique
• poisoning from contaminants added to 'cut' or dilute heroin.

Withdrawal symptoms

The withdrawal syndrome from heroin (or any other short-acting opioid) can begin within 12 hours of discontinuation of the sustained use of the drug: sweating, malaise, anxiety, depression, persistent and intense penile erection in males (priapism), general feeling of heaviness, cramp-like pains in the limbs, yawning and lachrymation, sleep difficulties, nausea and vomiting, diarrhoea, cramps and fever occur. Many addicts also complain of a painful condition, the so-called "itchy blood". Abrupt termination of heroin use causes muscle spasms in the legs of the user, hence the term "kicking the habit." However, it must be noted that each person's symptoms can be unique. There is also a significant risk of tonic-clonic or grand mal seizures (although less so than during withdrawal from sedatives such as barbiturates), which can lead to stroke possibly resulting in permanent disability including blindness or paralysis, or heart attacks, which can potentially be fatal. Users seeking to take the "cold-turkey" (without any preparation or accompaniments) approach are generally more likely to experience the negative effects of withdrawals.

Two general approaches are available to ease opioid withdrawal. The first is to substitute a longer-acting opioid such as methadone for heroin or another short-acting opioid and then slowly taper the dose. The other approach, which can be used alone or in combination, is to relieve withdrawal symptoms with non-opioid medications.

In the second approach, benzodiazepines such as diazepam (Valium) ease the often extreme anxiety of opioid withdrawal. Many symptoms of opioid withdrawal are due to rebound hyperactivity of the sympathetic nervous system, and this can be effectively suppressed with clonidine (Catapres), a centrally-acting alpha-2 agonist primarily used to treat hypertension. Many addicts who have been through these programs say that the agony of withdrawal is very much attenuated.

For those who repeatedly fail attempts at complete detoxification and relapse to heroin use, maintenance with regular doses of methadone is recommended.

Drug interactions

Opiates are strong central nervous system depressants, but regular users develop physiological tolerance allowing gradually increased dosages. In combination with other central nervous system depressants, heroin may still kill experienced users.

Toxicology studies of heroin overdose deaths reveal frequent involvement of other central nervous system depressants, including alcohol, benzodiazepines such as valium, and occasionally methadone. Ironically, benzodiazepines and methadone are often used in the treatment of heroin addiction.

Cocaine also proves to be often fatal when used in combination with heroin. Though "speedballs" (when injected) or "moonrocks" (when smoked) are a popular mix of the two drugs used among addicts, combinations of stimulants and depressants can have unpredictable and sometimes fatal results.

A heroin overdose is usually treated with an opioid antagonist, such as naloxone (Narcan) or naltrexone, which have a high affinity for opioid receptors but do not activate them. This blocks heroin and other opioid agonists and causes an immediate return of consciousness and start of withdrawal symptoms when administered intraveneously.

Cultural influences

Due to both the dramatic effects of the drug on the consumer's life and the widespread use of heroin amongst artists, heroin consumption and addiction has been featured in numerous works of art, ranging from songs and films to novels. Amongst these are:

Novels

• Basketball Diaries, The by Jim Carroll
• Cain's Book by Alexander Trocchi
• Drawing Of The Three, The, book 2 of The Dark Tower series by Stephen King
• Diary of a drug fiend by Aleister Crowley
• Jesus' Son by Denis Johnson
• Junk by Melvin Burgess
• Junky by William S. Burroughs
• Less Than Zero by Bret Easton Ellis
• The Man With the Golden Arm by Nelson Algren
• Naked Lunch by William S. Burroughs
• Requiem for a Dream by Hubert Selby
• Smack by Melvin Burgess
• Trainspotting by Irvine Welsh

Factual accounts

• The Heroin User's Handbook by Dr. Francis Moraes
• Permanent Midnight by Jerry Stahl
• The Survival of the Coolest by William Pryor
• Wir Kinder vom Bahnhof Zoo (life story of Christiane F. a teenage German addict)
• "Paranoid" Mick Wall
• "Getting off Right: A Safety Manual for Injection Drug Users" by Harm Reduction Coalition
• "How to Stop Time, Heroin from A-Z" by Anne Marlowe

Films

• Bad Lieutenant directed by Abel Ferrara
• The Crow directed by Alex Proyas
• French Connection II directed by John Frankenheimer
• Gridlock'd directed by Vondie Curtis-Hall
• More directed by Barbet Schroeder
• Naked Lunch directed by David Cronenberg
• Payback directed by Brian Helgeland
• Permanent Midnight directed by David Veloz
• Pulp Fiction directed by Quentin Tarantino
• Ray directed by Taylor Hackford
• Requiem for a Dream directed by Darren Aronofsky
• Rush directed by Lili Zanuck
• The Salton Sea directed by D.J. Caruso
• Sid and Nancy directed by Alex Cox
• Trainspotting directed by Danny Boyle
• Wasted directed by Stephen T. Kay

Songs

• "Heroin," "I'm Waiting for the Man," "White Light/White Heat," and "Sister Ray" by The Velvet Underground
• "Macarthur Park" covered by Donna Summer
• "Voodoo" by Godsmack
• "Junkhead", "Real Thing", and "God Smack", by Alice in Chains
• "Junkie Man" by Tim Armstrong
• "Billy" by Bad Religion
• "Hand of Doom" by Black Sabbath
• "2x4" by Blind Melon
• "Beetlebum" by Blur
• "Heroin Girl" by Everclear
• "The Bewlay Brothers" and "China Girl" by David Bowie
• "Perfect Blue Buildings" by Counting Crows
• "Not If You Were the Last Junkie on Earth (Heroin Is So Passe)" by The Dandy Warhols
• "Givin' Up" by The Darkness
• "Aux enfants de la chance" and "My Lady Heroine" by Serge Gainsbourg
• "Baltimore Love Thing" by 50 cent
• "Jesus Shootin' Heroin" by The Flaming Lips
• "Surfin' on Heroin" by Forgotten Rebels
• "Black Balloon" by the Goo Goo Dolls
• "Mr. Brownstone" by Guns N' Roses
• "Mountain Song" by Jane's Addiction
• "Some Candy Talking" by The Jesus and Mary Chain
• "There She Goes" by The La's
• "Cold Turkey" by John Lennon
• "Signed D.C." by Love
• "The Needle and the Spoon" by Lynyrd Skynyrd
• "Use the Man" and "Poison Was the Cure" by Megadeth
• "Just One Fix" by Ministry
• "True Faith" by New Order
• "Dumb" by Nirvana
• "China Girl" and "Lust for Life" by Iggy Pop
• "Adios" by Rammstein
• "Heroin" by Q-Strange
• "Under the Bridge" by Red Hot Chili Peppers
• "Perfect Day" by Lou Reed
• "Braindead" by Red Red Meat
• "Junkie's Promise" by Sonic Youth
• "Dead Flowers", "Sister Morphine" and "Monkey Man" by The Rolling Stones
• "Needle in the Hay", "The White Lady Loves You More", and "King's Crossing" by Elliott Smith
• "Golden Brown" and "Skin Deep" by The Stranglers
• "Pool Shark" by Sublime
• "I Believe in You" by Talk Talk
• "Times of Trouble" by Temple of the Dog
• "Chinese Rocks" by The Heartbreakers and The Ramones (written by Richard Hell and Dee Dee Ramone)
• "Bad" and "Running to Stand Still" by U2
• "Fall to Pieces" by Velvet Revolver
• "Getting High Down Below" by Marty Willson-Piper
• "The Needle and the Damage Done" by Neil Young
• "Carmelita" by Warren Zevon
• "Opium Trail" by Thin Lizzy
• "Horrorshow" and "Skag and Bone Man" by The Libertines
• "Heroin or Suicide" by Leftover Crack
• "Gimme Heroin" By Morning Glory
• "Tension Head" by Queens of the Stone Age
• "Angel" by Sarah McLachlan
• "Nice Boys" by Rose Tattoo
• "Dead Men Tell No Tales" by Motörhead
• "Hurt" by Nine Inch Nails, famously covered by Johnny Cash
• "The Beast" by The Only Ones
• "The Addition" by Frank DeBlasi
• "Comfortably Numb" by Pink Floyd
• "Master of Puppets" by Metallica
• "Mutiny in heaven" by The Birthday Party
• "Sunday's slave" by Nick Cave and the Bad Seeds
• "Hateful" by The Clash
• "Chase The Dragon" by The Beasts of Bourbon
• "Opium" by Jump, Little Children
• "Poppies" by Marcy Playground
• "Mainliner" by Social Distortion
• "Lust for Life", "China Girl" by Iggy Pop
• "H." by Tool
• "Ljubav kao heroin" ("Love Like Heroin") by Laufer (Croatia)
• "Theme From a Nod", "Year Of The Horse" by White Star Line
• "Purple Pills" by D12/Eminem
• "Mojo Pin" by Jeff Buckley
• "Love In Vein" by Skinny Puppy

Musicals

• Rent by Jonathan Larson

See also

Template:Wikinews

• Black Tar Heroin
• List of famous opiate addicts
• Methadone
• Oxycodone
• Fentanyl
• Recreational drug use

External links

Template:Commons

• Forum about opiate addiction (http://www.heroin-detox.com)
• Geopium: Geopolitics of Illicit Drugs in Asia (French) (http://www.geopium.org)
• Good Drugs Guide (http://www.thegooddrugsguide.com/heroin/index.htm)
• Heroin Helper (http://www.heroinhelper.com/)
• From Flowers to Heroin (http://www.cia.gov/cia/publications/heroin/flowers_to_heroin.htm), CIA publication.
• The mismanagement of methadone (http://wired-vig.wired.com/wired/archive/13.04/bupe.html?pg=1&topic=bupe&topic_set=)
• An article on heroin production, from cultivation to the end (http://www.usdoj.gov/dea/pubs/intel/20026/20026.html)
• Erowid heroin vault (http://www.erowid.org/chemicals/heroin/heroin.shtml)

Books

• Heroin (1998) ISBN 1568381530
• Heroin Century (2002) ISBN 0415278996
• This is Heroin (2002) ISBN 1860744249

Analgesics edit (https://academickids.com:443/encyclopedia/index.php?title=Template:Analgesics&action=edit)
{Paracetamol (acetaminophen) } {Tetrahydrocannabinol} {Cannabinoids} {Ketamine}
NSAIDs edit (https://academickids.com:443/encyclopedia/index.php?title=Template:NSAIDs&action=edit) {Aspirin} {Celecoxib} {Diclofenac} {Ibuprofen} {Ketoprofen} {Ketorolac} {Naproxen} {Rofecoxib} {Indomethacin}
Opioids edit (https://academickids.com:443/encyclopedia/index.php?title=Template:Opioids&action=edit) {Alfentanil} {Buprenorphine} {Carfentanil} {Codeine} {Codeinone} {Dextropropoxyphene} {Dihydrocodeine} {Endorphin} {Fentanyl} {Heroin} {Hydrocodone} {Hydromorphone} {Methadone} {Morphine} {Morphinone} {Oxycodone} {Oxymorphone} {Pethidine} {Remifentanil} {Sufentanil} {Tramadol}

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