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    Fentanyl molecular structure

    Fentanyl Stats & Data

    Tnt Fent Fenty Fetty Actiq
    NPS DataHub
    MW528.6
    FormulaC28H36N2O8
    CAS990-73-8
    IUPACN-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide citrate
    SMILESCCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-].[H+].[H+].[H+]
    InChIKeyIVLVTNPOHDFFCJ-UHFFFAOYSA-N
    Phenethylamines; 2020/1. Von 2-Phenethylamin abgeleitete Verbindungen; 2021/1. Von 2-Phenethylamin abgeleitete Verbindungen; 2022/1. Von 2-Phenethylamin abgeleitete Verbindungen
    Chemical Class Opioid
    Psychoactive Class Depressant
    Half-Life 3-12 hours (varies by route and individual)

    Pharmacology

    DrugBank
    State Solid

    Description

    Fentanyl, a potent opioid agonist, was developed in the 1950s to fill a need for strong and rapid analgesia. Because of these characteristics, fentanyl is commonly used to treat chronic cancer pain or in anesthesia. Fentanyl is related to other opioids like morphine and oxycodone. Fentanyl's high potency has also made it a common adulterant in illicit drugs, especially heroin. In 2017, 47600 overdose deaths in the United States involved some opioid (over 2/3 of all overdose deaths). Opioid overdoses kill an average of 11 Canadians daily. Fentanyl was FDA approved in 1968.

    Mechanism of Action

    Fentanyl binds to opioid receptors, especially the mu opioid receptor, which are coupled to G-proteins. Activation of opioid receptors causes GTP to be exchanged for GDP on the G-proteins which in turn down regulates adenylate cyclase, reducing concentrations of cAMP. Reduced cAMP decreases cAMP dependant influx of calcium ions into the cell. The exchange of GTP for GDP results in hyperpolarization of the cell and inhibition of nerve activity.

    Pharmacodynamics

    Fentanyl produces strong analgesia through its activation of opioid receptors. It has a duration of action of several hours and a wider therapeutic index as patients develop tolerance to opioids. Fentanyl is associated with a risk of addiction and abuse and should not be mixed with alcohol or benzodiazepines.

    Metabolism

    Fentanyl is metabolized to a number of inactive metabolites. Fentanyl is 99% N-dealkylated to norfentanyl by cytochrome P450. It can also be amide hydrolyzed to despropionylfentanyl, or alkyl hydroxylated to hydroxyfentanyl which is N-dealkylated to hydroxynorfentanyl.

    Absorption

    Fentanyl sublingual tablets are 54% bioavailable, transmucosal lozenges are 50% bioavailable, buccal tablets are 65% bioavailable, sublingual spray is 76% bioavailable, and nasal spray is 20% more bioavailable than transmucosal (or approximately 64% bioavailable). Fentanyl transmucosal lozenges reach a Cmax of 0.4±0.1ng/mL for a 200µg dose and 2.5±0.6ng/mL for a 1600µg dose with a Tmax of 20-40 minutes. The AUC was 172±96ng\*min/mL for a 200µg dose and 1508±1360ng\*min/mL for a 1600µg dose. Fentanyl sublingual spray reached a Cmax of 0.20±0.06ng/mL for a 100µg dose and 1.61±0.60ng/mL for an 800µg dose with a Tmax of 0.69-1.25 hours, decreasing as the dose increased. The AUC was 1.25±0.67ng\*h/mL for a 100µg dose and 10.38±3.70ng\*h/mL for a 800µg dose. Fentanyl transdermal systems reached a Cmax of 0.24±0.20ng/mL with a Tmax of 3.6±1.3h for a 25µg/h dose. The AUC was 0.42±0.35ng/mL\*h. Fentanyl nasal spray reaches a Cmax of 815±301pg/mL with a Tmax of less than 1 hour for a 200µg/100µL dose. The AUC was 3772pg\*h/mL.

    Toxicity

    Fentanyl has an intravenous LD50 of 2.91mg/kg in rats, an oral LD50 of 18mg/kg in rats and 368mg/kg in mice. The LD50 in humans is not known. Symptoms of overdose include respiratory depression, somnolence, stupor, coma, skeletal muscle flaccidity, cold and clammy skin, pupillary constriction, pulmonary edema, bradycardia, hypotension, airway obstruction, atypical snoring, and death. In case of overdose, patients should receive naloxone or nalmefene to reverse the action of the opioids as well as supportive measures to maintain the airway or advanced life support in the case of cardiac arrest.

    Indication

    Fentanyl intravenous or intramuscular injections are indicated for short term analgesia during induction, maintenance, and recovery from general or regional anesthesia. These injections are also used with a neuroleptic for premedication, induction, and as an adjunct to maintenance of anesthesia. Finally, fentanyl intravenous or intramuscular injections are used with oxygen for anesthesia in high risk patients. Fentanyl sublingual tablets, transmucosal lozenges, buccal tablets, sublingual sprays, transdermal systems, and nasal sprays are indicated for the management of breakthrough pain in opioid tolerant cancer patients who require around the clock pain management.

    Half-life

    The half life of fentanyl is 7 hours. The half life of fentanyl sublingual spray is 5-12 hours.

    Protein Binding

    Fentanyl is 80-85% bound to plasma proteins. In one study, a 0.1µg/L solution of fentanyl was 77.9±1.1% bound to human serum albumin and 12.0±5.4% bound to α-1 acid glycoprotein. A 0.1µg/L solution of norfentanyl, the primary metabolite of fentanyl, was 7.62±1.2% bound to human serum albumin and 7.24±1.9% bound to α-1 acid glycoprotein.

    Elimination

    Within 72 hours, 75% of a dose of fentanyl is excreted in the urine with <7% unchanged, and 9% is excreted in the feces with <1% unchanged.

    Volume of Distribution

    The intravenous volume of distribution is 4L/kg (3-8L/kg). The oral volume of distribution is 25.4L/kg. In hepatically impaired patients, the intravenous volume of distribution ranges from 0.8-8L/kg. Fentanyl crosses the blood brain barrier and the placenta.

    Clearance

    Total plasma clearance of fentanyl is 0.5L/hr/kg (0.3-0.7L/hr/kg) or 42L/hr. Following an intravenous dose, surgical patients displayed a clearance of 27-75L/h, hepatically impaired patients displayed a clearance of 3-80L/h, and renally impaired patients displayed a clearance of 30-78L/h.

    Receptor Profile

    Receptor Actions

    Agonists
    μ-opioid receptor agonist (full)

    Receptor Binding

    Mu-type opioid receptor agonist
    Delta-type opioid receptor agonist
    Kappa-type opioid receptor agonist
    ATP-dependent translocase ABCB1 inhibitor

    History & Culture

    1959–1968

    Fentanyl was first synthesized in 1959 by Belgian scientist Paul Janssen at Janssen Pharmaceutica, his relatively newly established pharmaceutical company. The compound was developed through systematic screening of chemical analogues of pethidine (marketed as Demerol) for enhanced opioid activity, with the goal of creating a potent and rapid-acting analgesic suitable for clinical use. The drug entered medical practice in 1968 when fentanyl citrate was approved by the FDA and introduced as a general anesthetic under the brand name Sublimaze, manufactured by McNeil Laboratories. The clinical success of fentanyl subsequently prompted the development of numerous structurally related analogues, including sufentanil, alfentanil, remifentanil, and the exceptionally potent carfentanil, all of which were subsequently introduced into medical practice.

    1990–2009

    In the mid-1990s, Janssen Pharmaceutica developed the Duragesic patch, a transdermal delivery system consisting of an inert alcohol gel infused with measured fentanyl doses designed to provide continuous opioid administration over 48 to 72 hours. Following successful clinical trials, this formulation significantly expanded fentanyl's applications in palliative care. The first rapid-acting fentanyl formulation for outpatient use appeared in 1998 with the introduction of Actiq, a flavored lollipop containing fentanyl citrate mixed with inert fillers intended for managing chronic breakthrough pain. Additional delivery methods followed, including the Fentora buccal tablet. In 2009, the FDA approved Onsolis, a buccal soluble film formulation designed for cancer pain management in opioid-tolerant patients. By 2012, fentanyl had become the most widely used synthetic opioid in clinical practice worldwide. Global medical consumption reached approximately 1,600 kilograms in 2015, and by 2019, it ranked as the 278th most commonly prescribed medication in the United States with over one million annual prescriptions. The drug is included on the World Health Organization's List of Essential Medicines.

    1970s–present

    Illicit use of pharmaceutical fentanyl and clandestinely produced analogues first emerged in the mid-1970s, initially appearing within medical professional communities with access to the drug. The street name "China White" came to refer to various illicitly manufactured fentanyl analogues, particularly α-methylfentanyl and 3-methylfentanyl. A significant outbreak of overdose deaths occurred in 2006 when illegally manufactured fentanyl, frequently mixed with cocaine or heroin, appeared in the United States and Canada. This wave of fatalities was heavily concentrated in Dayton, Chicago, Detroit, and Philadelphia. Beginning around 2013, overdose deaths involving illicit fentanyl began accelerating dramatically. By 2018, fentanyl had surpassed heroin as the primary driver of drug overdose mortality in the United States. While deaths from prescription opioids remained relatively stable between 2011 and 2021, synthetic opioid deaths—predominantly involving fentanyl—increased from approximately 2,600 to over 70,600 annually. In 2021, fentanyl and its analogues were responsible for more than 71,238 overdose deaths in the United States alone. Estonia has been documented as experiencing the world's longest continuous fentanyl epidemic, a situation exacerbated by disruptions to heroin supply following the Taliban's ban on opium cultivation in Afghanistan. Due to fentanyl's extreme lethality, the substance has been voluntarily prohibited by major darknet markets.

    2002–2018

    Fentanyl and its analogues have been employed in several notable governmental operations. During the Moscow theater hostage crisis in October 2002, Russian Spetsnaz security forces deployed an aerosolized chemical agent to incapacitate hostage-takers. The agent was widely suspected to be a fentanyl derivative, possibly carfentanil or remifentanil, though Russian authorities never officially confirmed the specific compound used. In August 2018, Nebraska became the first American state to use fentanyl as part of a lethal injection protocol. Carey Dean Moore, at that time one of the longest-serving death row inmates in the United States, was executed at Nebraska State Penitentiary using an intravenous sequence of four drugs that included fentanyl citrate to induce unconsciousness and respiratory suppression.

    Effect Profile

    Curated + 128 Reports
    Opioid 7.6

    Strong pain relief and sedation with moderate euphoria and itching/nausea

    Euphoria / Warmth×3
    78.0 6/20
    Analgesia×2
    105.9 2/20
    Sedation / Relaxation×1
    84.6 4/20
    Itching / Nausea×1
    67.9 3/20
    Catalog Erowid

    User Experiences

    Pain Relief "Carfentanyl is stronger hypnosedative under analgesic equivalent doses as fentanyl." Bluelight
    Sedation "(Cheap, good painkiller, not making me too tired (stimulating me!), easy to have a lifelong supply if you can control their usage a little, not being organotoxic at all, etc..)." Bluelight
    Euphoria "I felt as if there was alot of pressure in my head but it felt great, I was a little nervous of nodding and never waking up but effects subsided about 30 minutes later." Bluelight

    Tolerance & Pharmacokinetics

    drugs.wiki
    Half-Life
    3-12 hours (varies by route and individual)
    Addiction Potential
    Very high. Fentanyl is highly addictive with a significant risk of dependence, overdose, and death, especially when used outside medical supervision.

    Tolerance Decay

    Full tolerance 3d Half tolerance 7d Baseline ~21d

    Fentanyl tolerance decays significantly within 1–2 weeks of abstinence. Tolerance to analgesic effects is lost faster than tolerance to respiratory depression, creating a dangerous window where returning to a previous dose can cause fatal overdose. Even brief periods of abstinence (3–5 days) substantially reduce tolerance. Sources: StatPearls Fentanyl (NBK459275), PCSS Opioid Tolerance, American Addiction Centers.

    Cross-Tolerances

    Morphine
    85% ●●●
    Heroin
    85% ●●●
    Oxycodone
    80% ●●●
    Hydromorphone
    80% ●●●
    Methadone
    70% ●●○
    Codeine
    65% ●●○
    Tramadol
    50% ●●○
    Kratom
    40% ●○○

    Experience Report Analysis

    Erowid BlueLight
    108 Reports
    1995–2025 Date Range
    37 With Age Data
    26 Effects Detected

    Demographics

    Gender Distribution

    Age Distribution

    Reports Over Time

    Effect Analysis

    Erowid + Bluelight

    Effects aggregated from 128 experience reports (108 Erowid + 20 Bluelight)

    128 Reports
    70 Effects Detected
    29 Positive
    27 Adverse
    14 Neutral

    Effect Sentiment Distribution

    Confidence Distribution

    Positive Effects 29

    Euphoria 44.5% 93%
    Sedation 35.2% 89%
    Contentment 35.0% 84%
    Empathy 23.4% 85%
    Anxiety Suppression 20.3% 80%
    Thought Deceleration 20.0% 84%
    Stimulation 19.5% 80%
    Tactile Enhancement 16.7% 70%
    Pain Relief 16.4% 88%
    Body High 15.7% 89%
    Peace 15.0% 87%
    Sociability Enhancement 15.0% 89%
    Focus Enhancement 13.0% 70%
    Music Enhancement 10.2% 70%
    Color Enhancement 10.2% 70%
    Heaviness 10.0% 85%
    Love 10.0% 88%
    Warmth 10.0% 90%
    Joy 10.0% 85%
    Drowsiness 5.0% 85%

    Adverse Effects 27

    Nausea 31.3% 88%
    Vomiting 20.0% 91%
    Confusion 10.2% 70%
    Numbness 10.0% 88%
    Insomnia 10.0% 92%
    Body Load 10.0% 80%
    Hot Flashes 10.0% 85%
    Headache 7.0% 78%
    Motor Impairment 6.2% 90%
    Increased Heart Rate 5.6% 70%
    Memory Suppression 5.6% 70%
    Sweating 5.6% 70%
    Respiratory Suppression 5.0% 95%
    Fear 5.0% 95%
    Panic 5.0% 90%
    Dizziness 5.0% 88%
    Eye Strain 5.0% 75%
    Vibrating 5.0% 85%
    Thought Disorganization 5.0% 88%
    Emotional Blunting 5.0% 85%

    Dose-Response Correlation

    How effect frequency changes across dose levels

    View data table
    Effect Threshold (n=12)
    Hospital 58.3%
    Euphoria 41.7%
    Nausea 33.3%
    Anxiety Suppression 33.3%
    Sedation 33.3%
    Body High 25.0%
    Stimulation 25.0%
    Tactile Enhancement 16.7%
    Empathy 16.7%
    Music Enhancement 16.7%
    Focus Enhancement 16.7%
    Headache 16.7%
    Confusion 16.7%

    Dose–Effect Mapping

    Experience Reports

    How reported effects shift across dose tiers, based on 108 experience reports.

    Limited tier coverage — most reports fall within the Threshold range. Effects at other dose levels may not be represented.

    Effect Threshold (n=12)
    hospital
    58%
    euphoria
    42%
    nausea
    33%
    anxiety suppression
    33%
    sedation
    33%
    body high
    25%
    stimulation
    25%
    tactile enhancement
    17%
    empathy
    17%
    music enhancement
    17%
    focus enhancement
    17%
    headache
    17%
    confusion
    17%

    Dosage Distribution

    Dose distribution from experience reports

    Median: 100.0 µg IQR: 50.0–2400.0 µg n=16

    Real-World Dose Distribution

    62K Doses

    From 96 individual dose entries

    Sublingual (n=16)

    Median: 0.17mg 25th: 0.09mg 75th: 0.5mg 90th: 1.0mg
    mg/kg median: 0.002 mg/kg 75th: 0.012

    Intravenous (n=7)

    Median: 0.2mg 25th: 0.1mg 75th: 0.28mg 90th: 0.3mg
    mg/kg median: 0.003 mg/kg 75th: 0.004

    Transdermal (n=34)

    Median: 0.05mg 25th: 0.03mg 75th: 0.1mg 90th: 0.1mg
    mg/kg median: 0.001 mg/kg 75th: 0.001

    Oral (n=7)

    Median: 0.38mg 25th: 0.08mg 75th: 0.7mg 90th: 1.12mg
    mg/kg median: 0.006 mg/kg 75th: 0.016

    Common Combinations

    Most co-occurring substances in experience reports

    Form / Preparation

    Most common forms and preparations reported

    Body-Weight Dosing

    Dose relative to body weight from reports with weight data

    Sublingual

    Median: 0.002 mg/kg IQR: 0.002–0.002 mg/kg n=6

    Unknown

    Median: 0.007 mg/kg IQR: 0.001–0.024 mg/kg n=7

    Transdermal

    Median: 0.001 mg/kg IQR: 0.001–0.031 mg/kg n=16

    Oral

    Median: 0.001 mg/kg IQR: 0.001–0.005 mg/kg n=5

    Redose Patterns

    Redosing behavior across 91 reports

    15.4% Redosed
    1.2 Avg Doses

    Opioid Equivalence (MME)

    NIH HEAL 2024 & CDC 2022
    ⚠ Citation & Disclaimer: Conversion factors sourced from the NIH HEAL Initiative MME Calculator (Adams et al., PAIN 2025), the CDC 2022 Clinical Practice Guideline for Prescribing Opioids for Pain, and the MDCalc MME Calculator. These are approximate equianalgesic ratios for educational reference only. Individual responses vary significantly based on genetics, tolerance, cross-tolerance, and route of administration. This is not medical advice. Do not use these conversions to adjust opioid dosing without professional medical guidance.
    0.077 mg Fentanyl 10 mg Morphine (oral)
    MME factor 130×

    Fentanyl ~77 µg buccal ≈ 10 mg Morphine oral (buccal factor 0.13)

    Extremely potent. Multiple formulations with different factors: buccal 0.13, oral lozenge 0.18, nasal 0.16, transdermal patch 2.4 per µg/hr. Evidence level: Very Low (D) for buccal; High (A) for patch.

    Legal Status

    Country Status Notes
    Australia Schedule 8 Classified as a Schedule 8 controlled drug, meaning it is available for legitimate medical use under strict prescription controls. Additionally designated as a border controlled substance under Criminal Code Act 9.1.314, with further restrictions imposed by individual states and territories. Unauthorized possession, production, or supply is prohibited.
    Austria Prescription only (SMG/AMG) Legal for medical use under the Arzneimittelgesetz (AMG). Unauthorized sale or possession without a prescription is illegal under the Suchtmittelgesetz (SMG, Narcotic Substances Act).
    Canada Schedule I CDSA Controlled under Schedule I of the Controlled Drugs and Substances Act. Medical use requires prescription. In some jurisdictions such as Ontario, patients prescribed fentanyl patches must return used patches to pharmacies before receiving prescription refills as a diversion prevention measure.
    Germany Anlage III BtMG Listed in Anlage III of the Betäubungsmittelgesetz (Narcotics Act), indicating it is a marketable and prescription-capable narcotic. Can only be prescribed using a special narcotic prescription form (Betäubungsmittelrezept).
    Italy Tabella I Listed in Tabella I of the official tables of narcotic and psychotropic substances maintained by the Ministry of Health. Possession, purchase, and sale without authorization are illegal.
    Netherlands List I (Opiumwet) Classified as a List I substance under the Opium Act. Medical use permitted with prescription, but unauthorized possession, production, and distribution are criminal offenses.
    Russia Schedule II Controlled as a Schedule II substance under Russian drug control legislation. Medical use permitted under strict controls; unauthorized possession and distribution are prohibited.
    Switzerland Verzeichnis A Specifically named in Verzeichnis A (List A) of controlled substances. Medicinal use is permitted with appropriate authorization, but non-medical possession and supply are prohibited.
    Turkey Red prescription only Designated as a 'red prescription' substance, the most restricted prescription category in Turkey. Illegal to sell or possess without a valid prescription from an authorized physician.
    United Kingdom Class A Controlled under the Misuse of Drugs Act 1971. Medical use permitted with appropriate prescription, but unauthorized possession, production, or supply carries severe criminal penalties.
    United States Schedule II Controlled under the Controlled Substances Act as a Schedule II opiate. FDA approved for medical use since 1968. Illegal to sell without a DEA license and illegal to possess without a valid prescription. Certain formulations such as Abstral require distributors to implement FDA-approved risk evaluation and mitigation strategy (REMS) programs.

    Harm Reduction

    drugs.wiki

    Fentanyl is extremely potent (about 50-100x morphine). Overdose risk is high, especially with illicit or unknown dosages. Illicit fentanyl is a major driver of opioid overdose deaths. Naloxone can reverse fentanyl overdose but may require higher/multiple doses. Use only as prescribed and avoid mixing with other CNS depressants.

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