HOME
The Info List - Theophylline


--- Advertisement ---



Theophylline, also known as 1,3-dimethylxanthine, is a methylxanthine drug used in therapy for respiratory diseases such as chronic obstructive pulmonary disease (COPD) and asthma under a variety of brand names. As a member of the xanthine family, it bears structural and pharmacological similarity to theobromine and caffeine, and is readily found in nature, and is present in tea (Camellia sinensis) and cocoa (Theobroma cacao). A small amount of theophylline is one of the products of caffeine metabolic processing in the liver.[1]

Contents

1 Medical uses

1.1 Uses under investigation

2 Adverse effects 3 Mechanisms of action 4 Natural occurrences 5 Pharmacokinetics

5.1 Absorption 5.2 Distribution 5.3 Metabolism 5.4 Elimination

6 History 7 References 8 External links

Medical uses[edit] The main actions of theophylline involve:

relaxing bronchial smooth muscle increasing heart muscle contractility and efficiency; as a positive inotrope increasing heart rate: (positive chronotropic)[2] increasing blood pressure increasing renal blood flow anti-inflammatory effects central nervous system stimulatory effect mainly on the medullary respiratory center.

The main therapeutic uses of theophylline are aimed at:

chronic obstructive pulmonary disease (COPD) asthma infant apnea Blocks the action of adenosine; an inhibitory neurotransmitter that induces sleep, contracts the smooth muscles and relaxes the cardiac muscle.

Uses under investigation[edit] A clinical study reported in 2008 that theophylline was helpful in improving the sense of smell in study subjects with anosmia.[3] Adverse effects[edit] The use of theophylline is complicated by its interaction with various drugs and by the fact that it has a narrow therapeutic window.[quantify] Its use must be monitored by direct measurement of serum theophylline levels to avoid toxicity. It can also cause nausea, diarrhea, increase in heart rate, abnormal heart rhythms, and CNS excitation (headaches, insomnia, irritability, dizziness and lightheadedness).[4][5] Seizures can also occur in severe cases of toxicity, and are considered to be a neurological emergency.[6] Its toxicity is increased by erythromycin, cimetidine, and fluoroquinolones, such as ciprofloxacin. It can reach toxic levels when taken with fatty meals, an effect called dose dumping.[7] Theophylline
Theophylline
toxicity can be treated with beta blockers. In addition to seizures, tachyarrhythmias are a major concern.[8] Mechanisms of action[edit] Like other methylated xanthine derivatives, theophylline is both a

competitive nonselective phosphodiesterase inhibitor,[9] which raises intracellular cAMP, activates PKA, inhibits TNF-alpha[10][11] and inhibits leukotriene[12] synthesis, and reduces inflammation and innate immunity[12] nonselective adenosine receptor antagonist,[13] antagonizing A1, A2, and A3 receptors almost equally, which explains many of its cardiac effects

Theophylline
Theophylline
has been shown to inhibit TGF-beta-mediated conversion of pulmonary fibroblasts into myofibroblasts in COPD and asthma via cAMP-PKA pathway and suppresses COL1 mRNA, which codes for the protein collagen.[14] It has been shown that theophylline may reverse the clinical observations of steroid insensitivity in patients with COPD and asthmatics who are active smokers (a condition resulting in oxidative stress) via a distinctly separate mechanism. Theophylline
Theophylline
in vitro can restore the reduced HDAC (histone deacetylase) activity that is induced by oxidative stress (i.e., in smokers), returning steroid responsiveness toward normal.[15] Furthermore, theophylline has been shown to directly activate HDAC2.[15] (Corticosteroids switch off the inflammatory response by blocking the expression of inflammatory mediators through deacetylation of histones, an effect mediated via histone deacetylase-2 (HDAC2). Once deacetylated, DNA is repackaged so that the promoter regions of inflammatory genes are unavailable for binding of transcription factors such as NF-κB
NF-κB
that act to turn on inflammatory activity. It has recently been shown that the oxidative stress associated with cigarette smoke can inhibit the activity of HDAC2, thereby blocking the anti-inflammatory effects of corticosteroids.) Natural occurrences[edit] Theophylline
Theophylline
is naturally found in cocoa beans. Amounts as high as 3.7 mg/g have been reported in Criollo cocoa beans.[16] Trace amounts of theophylline are also found in brewed tea, although brewed tea provides only about 1 mg/L,[17] which is significantly less than a therapeutic dose. Pharmacokinetics[edit] Absorption[edit] When theophylline is administered intravenously, bioavailability is 100% (citation needed) Distribution[edit] Theophylline
Theophylline
is distributed in the extracellular fluid, in the placenta, in the mother's milk and in the central nervous system. The volume of distribution is 0.5 L/kg. The protein binding is 40%. The volume of distribution may increase in neonates and those suffering from cirrhosis or malnutrition, whereas the volume of distribution may decrease in those who are obese. Metabolism[edit] Theophylline
Theophylline
is metabolized extensively in the liver (up to 70%). It undergoes N-demethylation
N-demethylation
via cytochrome P450 1A2. It is metabolized by parallel zero order and Michaelis-Menten pathways. Metabolism may become saturated (non-linear), even within the therapeutic range. Small dose increases may result in disproportionately large increases in serum concentration. Methylation
Methylation
to caffeine is also important in the infant population. Smokers and people with hepatic (liver) impairment metabolize it differently. Both THC and nicotine have been shown to increase the rate of theophylline metabolism.[18] Elimination[edit] Theophylline
Theophylline
is excreted unchanged in the urine (up to 10%). Clearance of the drug is increased in children (age 1 to 12), teenagers (12 to 16), adult smokers, elderly smokers, as well as in cystic fibrosis, and hyperthyroidism. Clearance of the drug is decreased in these conditions: elderly, acute congestive heart failure, cirrhosis, hypothyroidism and febrile viral illness. The elimination half-life varies: 30 hours for premature neonates, 24 hours for neonates, 3.5 hours for children ages 1 to 9, 8 hours for adult non-smokers, 5 hours for adult smokers, 24 hours for those with hepatic impairment, 12 hours for those with congestive heart failure NYHA class I-II, 24 hours for those with congestive heart failure NYHA class III-IV, 12 hours for the elderly. History[edit] Theophylline
Theophylline
was first extracted from tea leaves and chemically identified around 1888 by the German biologist Albrecht Kossel.[19][20] Seven years later, a chemical synthesis starting with 1,3-dimethyluric acid was described by Emil Fischer and Lorenz Ach.[21] The Traube purine synthesis, an alternative method to synthesize theophylline, was introduced in 1900 by another German scientist, Wilhelm Traube.[22] Theophylline's first clinical use came in 1902 as a diuretic.[23] It took an additional 20 years until it was first reported as an asthma treatment.[24] The drug was prescribed in a syrup up to the 1970s as Theostat 20 and Theostat 80, and by the early 1980s in a tablet form called Quibron. References[edit]

^ Mandal, Ananya. " Caffeine
Caffeine
Pharmacology". Website Medical News.  ^ Alboni et al. Effects of Permanent Pacemaker and Oral Theophylline in Sick Sinus Syndrome The THEOPACE Study: A Randomized Controlled Trial ^ For Some Who Have Lost Their Sense Of Smell, A Once Popular Asthma Drug Could Help. Science Daily, American Physiological Society ^ MedlinePlus Drug Information: Theophylline ^ THEOPHYLLINE - ORAL 24 HOUR TABLET (Uni-Dur) side effects, medical uses, and drug interactions ^ Yoshikawa H (Apr 2007). "First-line therapy for theophylline-associated seizures". Acta Neurol Scand. 115 (4 Suppl): 57–61. doi:10.1111/j.1600-0404.2007.00810.x. PMID 17362277.  ^ Hendeles L, Weinberger M, Milavetz G, Hill M, Vaughan L (1985). "Food-induced "dose-dumping" from a once-a-day theophylline product as a cause of theophylline toxicity". Chest. 87 (6): 758–65. doi:10.1378/chest.87.6.758. PMID 3996063.  ^ Seneff M, Scott J, Friedman B, Smith M (1990). "Acute theophylline toxicity and the use of esmolol to reverse cardiovascular instability". Annals of Emergency Medicine. 19 (6): 671–3. doi:10.1016/s0196-0644(05)82474-6. PMID 1971502.  ^ Essayan DM (2001). "Cyclic nucleotide phosphodiesterases". J Allergy Clin Immunol. 108 (5): 671–80. doi:10.1067/mai.2001.119555. PMID 11692087.  ^ Deree J, Martins JO, Melbostad H, Loomis WH, Coimbra R (2008). "Insights into the Regulation of TNF-α Production in Human Mononuclear Cells: The Effects of Non-Specific Phosphodiesterase Inhibition". Clinics (Sao Paulo). 63 (3): 321–8. doi:10.1590/S1807-59322008000300006. PMC 2664230 . PMID 18568240.  ^ Marques LJ, Zheng L, Poulakis N, Guzman J, Costabel U (February 1999). " Pentoxifylline
Pentoxifylline
inhibits TNF-alpha production from human alveolar macrophages". Am. J. Respir. Crit. Care Med. 159 (2): 508–11. doi:10.1164/ajrccm.159.2.9804085. PMID 9927365.  ^ a b Peters-Golden M, Canetti C, Mancuso P, Coffey MJ (2005). "Leukotrienes: underappreciated mediators of innate immune responses". J. Immunol. 174 (2): 589–94. doi:10.4049/jimmunol.174.2.589. PMID 15634873.  ^ Daly JW, Jacobson KA, Ukena D (1987). " Adenosine
Adenosine
receptors: development of selective agonists and antagonists". Prog Clin Biol Res. 230 (1): 41–63. PMID 3588607.  ^ Yano Y, Yoshida M, Hoshino S, Inoue K, Kida H, Yanagita M, Takimoto T, Hirata H, Kijima T (2006). "Anti-fibrotic effects of theophylline on lung fibroblasts". Biochemical and Biophysical Research Communications. 341 (3): 684–90. doi:10.1016/j.bbrc.2006.01.018. PMID 16430859.  ^ a b Ito K, Lim S, Caramori G, Cosio B, Chung KF, Adcock IM, Barnes PJ (2002). "A molecular mechanism of action of theophylline: Induction of histone deacetylase activity to decrease inflammatory gene expression". Proceedings of the National Academy of Sciences of the United States of America. 99 (13): 8921–6. doi:10.1073/pnas.132556899. PMC 124399 . PMID 12070353.  ^ Apgar, Joan L; Tarka, Stanly M. Jr. (1998). "Methylxanthine composition and consumption patterns of cocoa and chocolate products and their uses". In Gene A. Spiller. Caffeine. CRC Press. p. 171. ISBN 0-8493-2647-8. Retrieved 2013-11-10.  ^ MAFF Food Surveillance Information Sheet ^ "RxList Marinol Interactions". 2008-05-29. Retrieved 2013-06-02.  (accessdate may be 2013-02-06) ^ Kossel A (1888). "Über eine neue Base aus dem Pflanzenreich". Ber. Dtsch. Chem. Ges. 21: 2164–2167. doi:10.1002/cber.188802101422.  ^ Kossel A (1889). "Über das Theophyllin, einen neuen Bestandtheil des Thees". Hoppe-Seyler's Z. Physiol. Chem. 13: 298–308.  ^ Fischer E, Ach L (1895). "Synthese des Caffeins". Ber. Dtsch. Chem. Ges. 28 (3): 3139. doi:10.1002/cber.189502803156.  ^ Traube W (1900). "Der synthetische Aufbau der Harnsäure, des Xanthins, Theobromins, Theophyllins und Caffeïns aus der Cyanessigsäure]". Chem. Ber. 33 (3): 3035–3056. doi:10.1002/cber.19000330352.  ^ Minkowski O (1902). "Über Theocin (Theophyllin) als Diureticum". Ther. Gegenwart. 43: 490–493.  ^ Schultze-Werninghaus G, Meier-Sydow J (1982). "The clinical and pharmacological history of theophylline: first report on the bronchospasmolytic action in man by S. R. Hirsch in Frankfurt (Main) 1922". Clin. Allergy. 12 (2): 211–215. doi:10.1111/j.1365-2222.1982.tb01641.x. PMID 7042115. 

External links[edit]

Wikimedia Commons has media related to Theophylline.

v t e

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short-acting β2 agonists

Bitolterol Carbuterol Fenoterol Isoetarine Pirbuterol Procaterol Reproterol Rimiterol Salbutamol
Salbutamol
(albuterol)#/ Levosalbutamol
Levosalbutamol
(levalbuterol) Terbutaline Tulobuterol

Long-acting β2 agonists

Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol Salmefamol

Ultra-long-acting β2 agonists

Abediterol Carmoterol Indacaterol Olodaterol Vilanterol

Other

Epinephrine# Hexoprenaline Isoprenaline
Isoprenaline
(isoproterenol) Orciprenaline
Orciprenaline
(metaproterenol)

Glucocorticoids

Beclometasone# Betamethasone Budesonide Ciclesonide Flunisolide Fluticasone Mometasone Triamcinolone

Anticholinergics/ muscarinic antagonist

Aclidinium bromide Glycopyrronium bromide Ipratropium bromide# Oxitropium bromide Tiotropium bromide Umeclidinium bromide

Mast cell stabilizers

Cromoglicate Nedocromil

Xanthines

Acefylline Ambuphylline Bamifylline Doxofylline Enprofylline Etamiphylline Proxyphylline Theophylline/Aminophylline/Choline theophyllinate

Eicosanoid
Eicosanoid
inhibition

Leukotriene
Leukotriene
antagonists

Montelukast Pranlukast Zafirlukast

Arachidonate 5-lipoxygenase inhibitors

Zileuton

Thromboxane receptor antagonists

Ramatroban Seratrodast

Non-xanthine PDE4 inhibitors

Ibudilast Roflumilast

Others/unknown

Amlexanox Eprozinol Fenspiride Omalizumab

Combination products

Aclidinium/formoterol Beclometasone/formoterol Beclometasone/formoterol/glycopyrronium Budesonide/formoterol Fluticasone
Fluticasone
furoate/vilanterol Fluticasone
Fluticasone
propionate/salmeterol Indacaterol/glycopyrronium bromide Ipratropium bromide/salbutamol Mometasone/formoterol Umeclidinium bromide/vilanterol

#WHO-EM ‡Withdrawn from market Clinical trials:

†Phase III §Never to phase III

v t e

Purine receptor
Purine receptor
modulators

Receptor (ligands)

P0 (adenine)

Agonists: 8-Aminoadenine Adenine

P1 (adenosine)

Agonists: 2-(1-Hexynyl)-N-methyladenosine 2-Cl-IB-MECA 2'-MeCCPA 4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil 5'-N-ethylcarboxamidoadenosine Adenosine ADP AMP Apadenoson ATL-146e ATP BAY 60–6583 Binodenoson Capadenoson CCPA CGS-21680 CP-532,903 Evodenoson GR 79236 LUF-5835 LUF-5845 N6-Cyclopentyladenosine Namodenoson Neladenoson dalanate Piclidenoson Regadenoson SDZ WAG 994 Selodenoson Sonedenoson Tecadenoson UK-432,097

Antagonists: 8-Chlorotheophylline 8-Phenyl-1,3-dipropylxanthine 8-Phenyltheophylline Acefylline Aminophylline ATL-444 Bamifylline Cafedrine Caffeine Caffeine
Caffeine
citrate Cartazolate CGH-2466 CGS-15943 Choline theophyllinate CPX CVT-6883 Dimethazan DMPX DPCPX Dyphylline Enprofylline Etazolate Fenethylline IBMX Isovaleric acid Istradefylline KF-26777 MRE3008F20 MRS-1220 MRS-1334 MRS-1706 MRS-1754 MRS-3777 Paraxanthine Pentoxifylline Preladenant Propentofylline Proxyphylline PSB-10 PSB-11 PSB-36 PSB-603 PSB-788 PSB-1115 Reversine Rolofylline SCH-442,416 SCH-58261 Theacrine Theobromine Theodrenaline Theophylline Tozadenant Tracazolate VUF-5574 ZM-241,385

P2 (nucleotide)

P2X (ATP)

Agonists: 2-Me-SATP α,β-Me-ATP Adenosine ADP AMP Ap4A Ap5A ATP ATPγS BzATP Cibacron blue CTP D-β,γ-Me-ATP GTP HT-AMP Ivermectin L-β,γ-Me-ATP MRS-2219 PAPET-ATP UTP Zinc

Antagonists: 5-BDBD A-317491 A-438079 A-740003 A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin
Emodin
(Rheum officinale) Evans Blue GW-791343 HMA Ip5I isoPPADS JNJ-47965567 KN-04 KN-62 Magnesium MRS-2159 NF-023 NF-110 NF-157 NF-279 NF-449 Opiranserin (VVZ-149) Oxidized-ATP Phenol Red Phenolphthalein PPADS PPNDS PSB-12062 Puerarin
Puerarin
(Radix puerariae) Purotoxin 1 RB-2 Ro 0437626 Ro 51 RO-3 Sodium ferulate
Sodium ferulate
(Angelica sinensis, Ligusticum wallichii) Suramin TC-P 262 Tetramethylpyrazine
Tetramethylpyrazine
(ligustrazine) (Ligusticum wallichii) TNP-ATP Zinc

P2Y

Agonists: 2-Me-SADP 2-Me-SATP 2-Thio-UTP 5-Br-UDP 5-OMe-UDP α,β-Me-ATP Adenosine ADP ADPβS Ap3A AR-C 67085MX ATP ATPγS CTP dATP Denufosol Diquafosol IDP ITP INS-365 INS-37217 MRS-2365 MRS-2690 MRS-2693 MRS-2768 MRS-2957 MRS-4062 NF-546 PAPET-ATP PSB-0474 PSB-1114 UDP UDPβS UDP-galactose UDP-glucose UDP-N-acetylglucosamine Up3U UTP UTPγS

Antagonists: 2-Me-SAMP A3P5PS AMPαS Ap4A AR-C 66096 AR-C 67085MX AR-C 69931MX AR-C 118925XX ATP BzATP C1330-7 Cangrelor Clopidogrel Elinogrel Ip5I MRS-2179 MRS-2211 MRS-2279 MRS-2395 MRS-2500 MRS-2578 NF-157 NF-340 PIT PPADS Prasugrel PSB-0739 RB-2 Regrelor Suramin Ticagrelor Ticlopidine UDP

Transporter (blockers)

CNTs

6-Hydroxy-7-methoxyflavone Adenosine dMeThPmR Estradiol KGO-2142 KGO-2173 MeThPmR Phloridzin Progesterone

ENTs

Barbiturates Benzodiazepines Cilostazol Dilazep Dipyridamole Estradiol Ethanol Hexobendine NBMPR Pentoxifylline Progesterone Propentofylline

PMAT

Decynium-22

Enzyme (inhibitors)

XO

Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol Myricetin Niraxostat Oxipurinol Phytic acid Pistacia integerrima Propolis Quercetin Tisopurine Topiroxostat

Others

Aminopterin Azathioprine Methotrexate Mycophenolic acid Pemetrexed Pralatrexate Many others

Others

Precursors: Adenine Adenosine AMP ADP ATP Cytosine Cytidine CMP CDP CTP Guanine Guanosine GMP GDP GTP Hypoxanthine Inosine IMP IDP ITP Ribose Uracil Uridine UMP UDP UTP

Others: Chrysophanol
Chrysophanol
(rhubarb)

See also: Receptor/signaling modulators

v t e

Phosphodiesterase inhibitors

PDE1

MMPX SCH-51866 Vinpocetine

PDE2

BAY 60-7550 Carbazeran EHNA Oxindole PDP

PDE3

Adibendan Amrinone
Amrinone
(inamrinone) Anagrelide Benafentrine Bucladesine Carbazeran Cilostamide Cilostazol Enoximone Imazodan KMUP-1 Meribendan Milrinone Olprinone Parogrelil Pimobendan Pumafentrine Quazinone RPL-554 Siguazodan Trequinsin Vesnarinone Zardaverine

PDE4

Apremilast Arofylline Atizoram Benafentrine Catramilast CC-1088 CDP-840 CGH-2466 Cilomilast Cipamfylline Crisaborole Denbutylline Drotaverine Etazolate Filaminast Glaucine HT-0712 ICI-63197 Indimilast Irsogladine Lavamilast Lirimilast Luteolin Mesembrenone Mesembrine Mesopram Oglemilast Piclamilast Pumafentrine Revamilast Ro 20-1724 Roflumilast Rolipram Ronomilast RPL-554 RS-25344 Tetomilast Tofimilast YM-976 Zardaverine

PDE5

Acetildenafil Aildenafil Avanafil Beminafil Benzamidenafil Dasantafil Icariin Gisadenafil Homosildenafil Lodenafil Mirodenafil MY-5445 Nitrosoprodenafil Norcarbodenafil SCH-51866 Sildenafil Sulfoaildenafil T-0156 Tadalafil Udenafil Vardenafil

PDE7

BRL-50481

PDE9

BAY 73-6691 PF-04447943

PDE10

Balipodect Mardepodect Papaverine TC-E 5005 Tofisopam

PDE11

BC11-38

Non-selective

Aminophylline Caffeine Choline theophyllinate CPX Dipyridamole Doxofylline Enprofylline Ibudilast IBMX Luteolin Paraxanthine Pentoxifylline Propentofylline Theobromine Theophylline Zaprinast

Unsorted

Diazepam Diprophylline DPCPX Furafylline Lisofylline MDL-12330A Moxaverine Oxagrelate Pentifylline Proxyphylline Quercetin Satigrel Tolafentrine Trapidil

See also: Receptor/signaling modulators

v t e

Stimulants

Adamantanes

Adapromine Amantadine Bromantane Memantine Rimantadine

Adenosine
Adenosine
antagonists

8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Paraxanthine SCH-58261 Theobromine Theophylline

Alkylamines

Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Levopropylhexedrine Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane

Ampakines

CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram

Arylcyclohexylamines

Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Benzazepines

6-Br-APB SKF-77434 SKF-81297 SKF-82958

Cholinergics

A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538

Convulsants

Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone

Eugeroics

Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol JZ-IV-10 Modafinil

Oxazolines

4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone

Phenethylamines

1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Ethylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MMA 4-Methylpentedrone 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine
Amphetamine
(Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine
Fenfluramine
(Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine IMP Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA
MDMA
(midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine
Methamphetamine
(Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N-Ethylbuphedrone N-Ethylhexedrone N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine (drug) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol
Salbutamol
(Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine

Phenylmorpholines

3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine

Piperazines

2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP oMPP Vanoxerine

Piperidines

1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate Methylphenidate
Methylphenidate
(Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate SCH-5472

Pyrrolidines

2-Diphenylmethylpyrrolidine 5-DBFPV α-PPP α-PBP α-PHP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone

Racetams

Oxiracetam Phenylpiracetam Phenylpiracetam
Phenylpiracetam
hydrazide

Tropanes

4-fluorotropacocaine 4'-Fluorococaine Altropane
Altropane
(IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane
Dichloropane
(RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (123I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121
RTI-121
(IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil
Troparil
(β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33

Tryptamines

4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT

Others

2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine

ATC code: N06B

Authority control

.