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Fentanyl
Systematic (IUPAC) name
N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenyl-propanamide
Identifiers
CAS number 437-38-7
ATC code N01AH01 N02AB03
PubChem 3345
DrugBank APRD00347
Chemical data
Formula C22H28N2O 
Mol. mass 336. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug A section of the Anatomical Therapeutic Chemical Classification System. A section of the Anatomical Therapeutic Chemical Classification System. PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 471 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 87. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 5 °C (190 °F)
Pharmacokinetic data
Bioavailability 92% (transdermal)
50% (buccal)
33% (ingestion)
Protein binding 80-85%
Metabolism hepatic, primarily by CYP3A4
Half life 7 hours (range 3–12 h)
Excretion Urine
Therapeutic considerations
Pregnancy cat.

C(US)
Legal status

Class A(UK) Schedule II(US)
Dependence Liability Moderate - High
Routes TD, IM, IV, oral, sublingual, buccal

Fentanyl is a powerful opioid analgesic with a potency approximately 81 times that of morphine. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of A drug's efficiency may be affected by the degree to which it binds to the proteins within Blood plasma. Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The liver is a vital organ in the human body and is present in Vertebrates and some other animals Cytochrome P450 3A4 (abbreviated CYP3A4) ( a member of the Cytochrome P450 mixed-function oxidase system is one of the most important enzymes involved in the metabolism The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical if it is used as directed by the mother during The United States of America —commonly referred to as the The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction The Misuse of Drugs Act 1971 (c38 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom, the UK or Britain,is a Sovereign state located The Controlled Substances Act ( CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control The United States of America —commonly referred to as the In Pharmacology and Toxicology, a route A transdermal patch or skin patch is a Medicated Adhesive patch that is placed on the Skin to deliver a specific Dose of medication Intramuscular injection is the injection of a substance directly into a Muscle. Intravenous therapy or IV therapy is the giving of Liquid substances directly into a Vein. Buccal mucosa is Mucous membrane of the inside of the Cheek. It is non-keratinised and is continuous with the mucosae of the soft palate under surface of tongue and An opioid is a chemical Substance that has a Morphine -like action in the body Medical uses Morphine can be used as an analgesic in hospital settings to relieve pain in Myocardial infarction pain in Fentanyl has an LD50 of 3. In Toxicology, the median lethal dose, LD50 (abbreviation for “Lethal Dose 50%” or LCt50 (Lethal Concentration & Time of a 1 milligrams per kilogram in rats and 0. 03 milligrams per kilogram in monkeys. The LD50 in humans, by intravenous injection in an opiate-naive individual (without tolerance), is 0. 5-1 milligrams. Due to its potency, its ability to subdue pain in a short period of time has warranted it a Schedule II drug in the United States. The Controlled Substances Act ( CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control

Contents

History

Fentanyl was first synthesized by Janssen Pharmaceutica (Belgium) in 1959, and was one of the first few on a long list of helpful pharmaceuticals produced by Paul Janssen's relatively new Janssen Pharmaceutica. Janssen Pharmaceutica, is a Pharmaceutical company based in Beerse, in the Campine region of the province of Antwerp, Belgium. The Kingdom of Belgium is a Country in northwest Europe. It is a founding member of the European Union and hosts its headquarters as well as those Paul Adriaan Jan Baron Janssen (born on 12 September 1926 in Turnhout, Belgium - 11 November, 2003 in Rome, Janssen Pharmaceutica, is a Pharmaceutical company based in Beerse, in the Campine region of the province of Antwerp, Belgium. Fentanyl was introduced into medical practice in the 1960s as an intravenous anesthetic under the trade name of Sublimaze. The 1960s decade refers to the years from the beginning of 1960 to the end of 1969 Anesthesia, or anaesthesia (see spelling differences; from Greek grc αν- an-, "without" and grc αἲσθησις

Chemistry

Synthesis

The synthesis of fentanyl (N-phenyl-N-(1-phenethyl-4-piperidinyl)propanamide) by Janssen Pharmaceutica was achieved in four steps, starting from 4-piperidinone hydrochloride. Janssen Pharmaceutica, is a Pharmaceutical company based in Beerse, in the Campine region of the province of Antwerp, Belgium. 4-Piperidinone (4-piperidone piperidin-4-one is a derivative of Piperidine with the Molecular formula C 5 H 9 N[[Oxygen The 4-piperidinone hydrochloride was first reacted with phenethyl bromide to give N-phenethyl-4-piperidinone (NPP). N -Phenethyl-4-piperidinone (NPP is a derivative of 4-piperidinone with the Molecular formula C 5 H 9 N[[Oxygen Treatment of the NPP intermediate with aniline followed by reduction with sodium borohydride afforded 4-anilino-N-phenethyl-piperidine (ANPP). Aniline, phenylamine or aminobenzene is an Organic compound with the formula C6H7N Sodium borohydride, also known as sodium tetrahydroborate, has the Chemical formula Na[[boron B]] H 4 Finally ANPP and propionic anhydride are reacted to form the amide product. Propanoic anhydride, also called propionic anhydride, is a simple Acid anhydride.

Analogues

The pharmaceutical industry has developed several analogues of fentanyl:

Therapeutic use

Fentanyls are extensively used for anesthesia and analgesia, most often in the operating room and intensive care unit. Anesthesia, or anaesthesia (see spelling differences; from Greek grc αν- an-, "without" and grc αἲσθησις Fentanyl transdermal patch (Durogesic/Duragesic) is used in chronic pain management. A transdermal patch or skin patch is a Medicated Adhesive patch that is placed on the Skin to deliver a specific Dose of medication Fentanyl patches work by releasing fentanyl into body fats, which then slowly release the drug into the blood stream over 48 to 72 hours, allowing for long lasting relief from pain. In the past few years, the patches have gone generic and are available for lower costs. A generic drug (generic drugs short generics is a drug which is produced and distributed without Patent protection Fentanyl patches are manufactured in five patch sizes: 12. 5 micrograms/h, 25 µg/h, 50 µg/h, 75 µg/h, and 100 µg/h. Dosage is based on the size of the patch, since the transdermal absorption rate is generally constant at a constant skin temperature. Rate of absorption is dependent on a number of factors. Body temperature, skin type, amount of body fat, and placement of the patch can have major effects. The different delivery systems used by different makers will also affect individual rates of absorption. The typical patch will take effect under normal circumstances usually within 8-12 hours, thus fentanyl patches are often prescribed with another opiate (such as morphine sulfate) to handle breakthrough-pain.

Fentanyl lozenges (Actiq) are a solid formulation of fentanyl citrate on a stick in the form of a lollipop that dissolves slowly in the mouth for transmucosal absorption. Actiq by Cephalon, is a solid formulation of Fentanyl citrate on a plastic stick that dissolves slowly in the Mouth for absorption across the Buccal A lollipop, pop, lolly, sucker, or sticky-pop is a type of Confectionery consisting mainly of hardened flavored Sucrose These lozenges are intended for opioid-tolerant individuals and are effective in treating breakthrough cancer pain. Most Cancer patients will from time to time experience pain which is normally treated by pain medications It is also useful for breakthrough pain for those suffering bone injuries, severe back pain, neuropathy, arthritis, and some other examples of chronic nonmalignant pain. The unit is a berry-flavored lozenge on a stick which is swabbed on the mucosal surfaces inside the mouth—inside of the cheeks, under and on the tongue and gums—to release the fentanyl quickly into the system. It is most effective when the lozenge is consumed in 15 minutes. The drug is less effective if swallowed, as despite good absorbance from the small intestine there is extensive first pass metabolism, leading to an oral bioavailability of 33%. Fentanyl lozenges are available in six dosages, from 200 to 1600 µg in 200 µg increments (excluding 1000 µg and 1400 µg). These are now available in the United states in generic form,[1] through an FTC consent agreement. [2]
However, most patients find it takes 10-15 minutes to use all of one lozenge, and those with a dry mouth cannot use this route. In addition, nurses are unable to document how much of a lozenge has been used by a patient, making drug records inaccurate. The development of small fentanyl buccal pellets (Fentora) may be much more practical. These are effervescent tablets placed in the cheek and are absorbed through the buccal mucosa. Cheeks ( Latin: buccae) constitute the area of the Face below the Eyes and between the Nose and the left or right Ear Buccal mucosa is Mucous membrane of the inside of the Cheek. It is non-keratinised and is continuous with the mucosae of the soft palate under surface of tongue and One advantage of such tablets is claimed to be quicker absorption into the bloodstream at lower dosage levels.

In palliative care transdermal fentanyl has a definite, but limited, role for:

Fentanyl is sometimes given intrathecally as part of spinal anesthesia or epidurally for epidural anesthesia and analgesia. Spinal analgesia, (or commonly called spinal anesthesia or sub-arachnoid block (S The term epidural is often short for epidural anesthesia, a form of Regional anesthesia involving injection of drugs through a Catheter placed into the The term epidural is often short for epidural anesthesia, a form of Regional anesthesia involving injection of drugs through a Catheter placed into the Because of fentanyl's high lipid solubility its effects are more localised than morphine and some clinicians prefer to use the morphine to get a wider spread of analgesia.


Adverse events

Fentanyl's major side effects (more than 10% of patients) include diarrhea, nausea, constipation, dry mouth, somnolence, confusion, asthenia,and sweating; and, less frequently (3 to 10% of patients), abdominal pain, headache, fatigue, anorexia and weight loss, dizziness, nervousness, hallucinations, anxiety, depression, flu-like symptoms, dyspepsia, dyspnea, hypoventilation, apnea, and urinary retention. Asthenia ( Greek: ασθένεια, lit lack of strength but also disease) is a medical term denoting symptoms of physical weakness Dyspepsia (from the Greek "δυς-" (Dys- and "πέψη" (Pepse known in plain English as indigestion, meaning hard Dyspnea or dyspnoea (pronounced disp-nee-ah, IPA /dɪsp'niə/ from Latin dyspnoea, from Greek dyspnoia from In Medicine, hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate ( hypo means "below" to perform needed Fentanyl use has also been associated with aphasia. [3]

Adverse effects

Like other lipid soluble drugs, the pharmacodynamics of fentanyl are poorly understood. The manufacturers acknowledge there is no data on the pharmacodynamics of fentanyl in elderly, cachectic or debilitated patients, frequently the type of patient for which transdermal fentanyl is being used. Cachexia (kəˈkɛksiə is loss of weight, Muscle atrophy, fatigue weakness and significant loss of appetite in someone who is not actively trying to This may explain the increasing number of reports of respiratory depression events since the late 1970s. In Medicine, hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate ( hypo means "below" to perform needed [4][5][6][7][8][9][10] In 2006 the U. S. Food and Drug Administration started investigating several respiratory deaths.

The precise reason for sudden respiratory depression is unclear, but there are several hypotheses:


Fentanyl has a therapeutic index of 270. The therapeutic index (also known as therapeutic ratio) is a comparison of the amount of a therapeutic agent that causes the therapeutic effect to the amount that causes toxic [11]

Illicit use

Fentanyl powder seized by a Lake County Deputy Sheriff in Painesville, Ohio, where a male subject had been discovered unresponsive and struggling to breathe
Fentanyl powder seized by a Lake County Deputy Sheriff in Painesville, Ohio, where a male subject had been discovered unresponsive and struggling to breathe

Illicit use of pharmaceutical fentanyls first appeared in the mid-1970s in the medical community and continues in the present. Lake County is a County located in the US state of Ohio. As of 2000 the population was 227511 Painesville is a city in Lake County, Ohio, United States, along the Grand River. Drug abuse has a wide range of definitions related to taking a Psychoactive drug or Performance enhancing drug for a non-therapeutic or non-medical effect This article is about the Decade 1970-1979 For the Year 1970 see 1970. United States authorities classify fentanyl as a narcotic. The term narcotic (ναρκωτικός is believed to have been coined by the Greek physician Galen to refer to agents that benumb or deaden causing loss To date, over 12 different analogues of fentanyl have been produced clandestinely and identified in the U. Clandestine chemistry generally refers to Chemistry carried out in illegal drug Laboratories (known colloquially as labs) but can include any S. drug traffic. The biological effects of the fentanyls are similar to those of heroin, with the exception that many users report a noticeably less euphoric 'high' associated with the drug and stronger sedative and analgesic effects. Heroin ( INN: diacetylmorphine, BAN: diamorphine) is a semi-synthetic opioid synthesized from Morphine, a derivative Because the effects of fentanyl last for only a very short time, it is even more addictive than heroin, and regular users may become addicted very quickly. Additionally, fentanyl may be hundreds of times more potent than street heroin, and tends to produce significantly worse respiratory depression, making it somewhat more dangerous than heroin to users — though in some places, it is sold as heroin, often leading to overdoses. In Medicine, hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate ( hypo means "below" to perform needed Fentanyl is most commonly used orally, but like heroin, can also be smoked, snorted or injected. Many fentanyl overdoses are initially classified as heroin overdoses. [12]

Fentanyl is normally sold on the black market in the form of transdermal fentanyl patches such as Duragesic, diverted from legitimate medical supplies. Duragesic and Durogesic (ˌdɚə'dʒiʒɪk are the trade names of Fentanyl transdermal therapeutic systems, and are used for moderate to severe pain relief The patches may be cut up and eaten, or the gel from inside the patch smoked. To prevent the removal of the fentanyl base, Janssen-Cilag, the inventor of the Fentanyl patch designed the Durogesic patch. Janssen-Cilag, a Johnson & Johnson subsidiary was founded in the early nineties by joining the marketing organizations of Cilag and Janssen Pharmaceutica The Durogesic patches contain their Fentanyl throughout the plastic matrix instead of gel incorporated into a reservoir on the patch. Manufacturers such as Mylan have also produced Durogesic style fentanyl patches that contain the chemical in a silicone matrix, preventing the removal of the fentanyl-containing gel present in other products. Duragesic and Durogesic (ˌdɚə'dʒiʒɪk are the trade names of Fentanyl transdermal therapeutic systems, and are used for moderate to severe pain relief [1] Another dosage form of fentanyl which has appeared on the streets are the fentanyl lollipops Actiq, which are sold under the street name of "percopop". Actiq by Cephalon, is a solid formulation of Fentanyl citrate on a plastic stick that dissolves slowly in the Mouth for absorption across the Buccal The pharmacy retail price ranges from US$10 to US$30 per unit (based on strength of lozenge), with the black market cost anywhere from US$15 to US$40 per unit, depending on the strength. The United States dollar ( sign: $; code: USD) is the unit of Currency of the United States; it has also been Non-medical use of fentanyl by individuals without opiate tolerance can be very dangerous and has resulted in numerous deaths. [2] Even those with opiate tolerances are at high risk for overdoses. Once the fentanyl is in the user's system it is extremely difficult to stop its course because of the nature of absorption. Illicitly synthesized fentanyl powder has also appeared on the US market. Because of the extremely high strength of pure fentanyl powder, it is very difficult to dilute appropriately, and often the resulting mixture may be far too strong and consequently very dangerous. Some heroin dealers mix fentanyl powder with larger amounts of heroin in order to increase potency or compensate for low-quality heroin, and to increase the volume of their product. As of December 2006, a mix of fentanyl and either cocaine or heroin has caused an outbreak in overdose deaths in the United States, heavily concentrated in the cities of Detroit, Philadelphia, Pittsburgh, St. Louis, Milwaukee, Camden, Chicago,[13] Little Rock, and Dallas. Cocaine ( benzoylmethyl ecgonine) is a Crystalline Tropane Alkaloid that is obtained from the leaves of the Coca plant Heroin ( INN: diacetylmorphine, BAN: diamorphine) is a semi-synthetic opioid synthesized from Morphine, a derivative Philadelphia (ˌfɪləˈdɛlfiə The City of Camden is the County seat of Camden County, New Jersey, in the United States. Chicago (ʃɪˈkɑːgoʊ is the largest City by population in the state of Illinois and the American Midwest of the United States. Little Rock is the Capital and the most populous city of the U [14] The mixture of fentanyl and heroin is known as "magic", among other names, on the street. [15]

Several large quantities of illicitly-produced fentanyl have been seized by U. S. law enforcement agencies. In June 2006, 945 grams of 83% pure fentanyl powder were seized by Border Patrol agents in California from a vehicle which had entered from Mexico. The United States Border Patrol is a federal law enforcement agency within U [16] Mexico is the source of much of the illicit fentanyl for sale in the U. S. However, there has been one domestic fentanyl lab discovered by law enforcement, in April 2006 in Azusa, California. Azusa is a city in Los Angeles County, California, United States. The lab was a source of counterfeit 80 mg OxyContin tablets containing fentanyl instead of oxycodone, as well as bulk fentanyl and other drugs. Oxycodone is an Opioid Analgesic Medication synthesized from Thebaine. [17][18]

The "china white" form of fentanyl refers to the clandestinely produced analogue α-methylfentanyl (AMF). α-methylfentanyl is an Opioid Analgesic that is an analogue of Fentanyl. [19] Although AMF is described as having a short duration of action (90 minutes), the main bonus of inserting the α-Me can be thought analogously to phenethylamines and amphetamines. The name amphetamine actually is based on chemical structure: alpha methyl phenethyl amines.

Thus, the motivation for AMF is that despite the extra difficulty from a synthetic stand-point, the resultant drug is relatively more resistant to metabolic degradation resulting in a drug with an increased duration. [20] This is particularly noteworthy since an article in JPET reported that the main metabolite for fentanyl in vivo is the N-dealkylated metabolite. Additionally, AMF is reported to be at least three times more potent than fentanyl.

References

  1. ^ Barr Pharmaceuticals (2006-09-27). Barr Pharmaceuticals Inc, ( is global specialty pharmaceutical company that operates in more than 30 countries worldwide and is engaged in the development manufacture and marketing Year 2006 ( MMVI) was a Common year starting on Sunday of the Gregorian calendar. Events 489 - Odoacer attacks Theodoric at the Battle of Verona and is defeated again "Barr Launches Generic ACTIQ(R) Cancer Pain Management Product". Press release. A news release, media release, press release or press statement is a written or recorded Communication directed at members of the News Retrieved on 2006-09-30. Year 2006 ( MMVI) was a Common year starting on Sunday of the Gregorian calendar. Events 1399 - Henry IV is proclaimed King of England. 1744 - France and Spain defeat the
  2. ^ FTC (2004-08-09). "MMIV" redirects here For the Modest Mouse album see " Baron von Bullshit Rides Again " Events 48 BC - Caesar's civil war: Battle of Pharsalus - Julius Caesar decisively defeats Pompey at Pharsalus "With Conditions, FTC Allows Cephalon’s Purchase of CIMA, Protecting Competition for Breakthrough Cancer Pain Drugs". Press release. A news release, media release, press release or press statement is a written or recorded Communication directed at members of the News Retrieved on 2006-09-30. Year 2006 ( MMVI) was a Common year starting on Sunday of the Gregorian calendar. Events 1399 - Henry IV is proclaimed King of England. 1744 - France and Spain defeat the
  3. ^ http://www.drugs.com/pro/fentanyl-transdermal.html#A02A9CB6-35CF-4F01-A980-C3733E0F861A
  4. ^ Smydo J. Delayed respiratory depression with fentanyl. Anesthesia Progress. 26(2):47-8, 1979
  5. ^ van Leeuwen L. Deen L. Helmers JH. A comparison of alfentanil and fentanyl in short operations with special reference to their duration of action and postoperative respiratory depression. Anaesthesist. 30(8):397-9, 1981
  6. ^ Brown DL. Postoperative analgesia following thoracotomy. Danger of delayed respiratory depression. Chest. 88(5):779-80, 1985.
  7. ^ Bulow HH. Linnemann M. Berg H. Lang-Jensen T. LaCour S. Jonsson T. Respiratory changes during treatment of postoperative pain with high dose transdermal fentanyl. Acta Anaesthesiologica Scandinavica, 1995; 39(6): 835-9.
  8. ^ Nilsson C. Rosberg B. Recurrence of respiratory depression following neurolept analgesia. Acta Anaesthesiologica Scandinavica. 26(3):240-1, 1982
  9. ^ McLoughlin R. McQuillan R. Transdermal fentanyl and respiratory depression. Palliative Medicine, 1997; 11(5):419.
  10. ^ Regnard C, Pelham A. Severe respiratory depression and sedation with transdermal fentanyl: four case studies. Palliative Medicine, 2003; 17: 714-716.
  11. ^ New Anesthetic Agents, Devices, and Monitoring Techniques. Retrieved on 2007-10-20. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1740 - Maria Theresa takes the throne of Austria. France, Prussia, Bavaria and Saxony
  12. ^ [Boddiger, D. (2006, August 12). Fentanyl-laced street drugs “kill hundreds”. In EBSCOhost. Retrieved March 7, 2007, from http://proxy.clpccd.cc.ca.us:2271/ehost/ pdf?vid=8&hid=8&sid=e6bcbd34-2854-4beb-bfca-35460dd686e6%40sessionmgr7 ]
  13. ^ Press Release by the Chicago Police Department Police report about a death linked to heroin/fentanyl mixture August 24, 2006
  14. ^ SMU student's death blamed on rare drug
  15. ^ Fentanyl probe nets 3 suspects by Norman Sinclair and Ronald J. Hansen, The Detroit News, June 23, 2006, retrieved June 25, 2006.
  16. ^ INTELLIGENCE ALERT: HIGH PURITY FENTANYL SEIZED NEAR WESTMORELAND, CALIFORNIA, DEA Microgram, June 2006
  17. ^ INTELLIGENCE ALERT: LARGE FENTANYL / MDA / TMA LABORATORY IN AZUZA, CALIFORNIA - POSSIBLY THE “OC-80” TABLET SOURCE, DEA Microgram, April 2006.
  18. ^ INTELLIGENCE ALERT: OXYCONTIN MIMIC TABLETS (CONTAINING FENTANYL) NEAR ATLANTIC, IOWA, DEA Microgram, January 2006.
  19. ^ Behind the Identification of China White Analytical Chemistry, 53(12), 1379A-1386A (1981)
  20. ^ Van Bever W, Niemegeers C, Janssen P (1974). "Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-(3-methyl-1-(2-phenylethyl)-4-piperidyl)-N-phenylpropanamide and N-(3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl)-N-phenylpropanamide". J Med Chem 17 (10): 1047–51. doi:10.1021/jm00256a003. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 4420811.  

See also

External links

A psychoactive drug or psychotropic substance is a Chemical substance that acts primarily upon the Central nervous system where it alters Brain The Moscow theater hostage crisis, also known as the 2002 Nord-Ost siege, was the seizure of a crowded Moscow Theatre on October 23

Dictionary

fentanyl

-noun

  1. (pharmacology) A particular narcotic painkiller.
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