Tacrine (CED0003989)

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:45 UTC

Update Date

2026-05-14 16:37:09 UTC

SynCED ID

CED0003989

Secondary Accession Numbers

CHEM002185
T3D2772

Identification

Common Name

Tacrine

Class

Small Molecule

Description

Tacrine is an exogenous organic compound with the formula C13H14N2 and an average molecular weight of 198.26 g/mol. It exists as a solid at room temperature. Tacrine belongs to the benzoquinolines, a subclass of quinolines and derivatives within the organic compounds. The compound functions as a biological and chemical inhibitor of acetylcholinesterase (EC 3.1.1.7). It acts by reversibly binding acetylcholinesterase to slow the degradation of acetylcholine released by intact cholinergic neurons, thereby elevating acetylcholine concentrations in the cerebral cortex. In addition to acetylcholinesterase, recorded protein targets include cholinesterase (BCHE), solute carrier family 22 member 1 (SLC22A1), solute carrier family 22 member 2 (SLC22A2), acetylcholine receptor subunit epsilon (CHRNE), and 11 other proteins. Tacrine is used as an anti-dementia drug and is recorded in 24 sources. These include healthcare, pharmaceuticals and veterinary products; food, food processing and cookware, such as the processing of meats and fish and the preparation of vinegar and wine or sparkling wine; household cleaning and consumer products, including perfumes within detergents and soaps, cigar cigarettes, pipe accessories, and non-electric simulated smoking devices; electrical and electronic equipment, including antennas, amplifiers, conductive bodies, and electrically stimulated smoking devices; and building and construction materials, specifically floors. The recorded exposure route for this compound is oral.

Contaminant Type

Amine
Cholinesterase Inhibitor
Drug
Human Neurotoxin
Metabolite
Nootropic Agent
Organic Compound
Parasympathomimetic
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2,3,4-Tetrahydro-9-acridinamine	ChEBI
1,2,3,4-Tetrahydro-9-aminoacridine	ChEBI
5-Amino-6,7,8,9-tetrahydroacridine	ChEBI
9-Amino-1,2,3,4-tetrahydroacridine	ChEBI
Tetrahydroaminacrine	ChEBI
Tacrinal	Kegg
Tetrahydroaminoacridine	HMDB
Tetrahydroaminocrin	HMDB
Tetrahydroaminocrine	HMDB
THA	HMDB
1,2,3,4-Tetrahydroaminoacridine	HMDB
Horizon brand OF tacrine hydrochloride	HMDB
OTL pharm brand OF tacrine hydrochloride	HMDB
Parke davis brand OF tacrine hydrochloride	HMDB
Tenakrin	HMDB
Romotal	HMDB
Cognex	HMDB
Tacrine hydrochloride	HMDB
Woods brand OF tacrine hydrochloride	HMDB

Chemical Formula

C₁₃H₁₄N₂

Average Molecular Mass

198.264 g/mol

Monoisotopic Mass

198.116 g/mol

CAS Registry Number

321-64-2

IUPAC Name

1,2,3,4-tetrahydroacridin-9-amine

Traditional Name

tacrine

SMILES

NC1=C2CCCCC2=NC2=CC=CC=C12

InChI Identifier

InChI=1S/C13H14N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1,3,5,7H,2,4,6,8H2,(H2,14,15)

InChI Key

YLJREFDVOIBQDA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridines

Alternative Parents

Substituents

Acridine
4-aminoquinoline
Aminoquinoline
Aminopyridine
Benzenoid
Pyridine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic amine (CHEBI:45980 )
acridines (CHEBI:45980 )
a small molecule (CPD-10887 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

EC 3.1.1.7 (acetylcholinesterase) inhibitor (PMC2669703 , PMC13074758 )?An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
EC 3.1.1.8 (cholinesterase) inhibitor (PMC11834182 , PMC11834182 )?An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
cholinergic drug (PMC9143817 )?
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor (PMC5997408 , PMC5997408 )?
drug (PMC4525150 )?
inhibitor (PMC8615659 , PMC7517894 )?

Chemical Roles

EC 3.1.1.7 (acetylcholinesterase) inhibitor ?

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	183.5°C
Boiling Point	Not Available
Solubility	217 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.13	ALOGPS
logP	2.63	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	8.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.91 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	61.74 m³·mol⁻¹	ChemAxon
Polarizability	22.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00r2-0900000000-e2921d2cb64d7c502a4b	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-453e4e963f034e9de4cf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-256a5702a96325bc74f2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-af483bfb98e7e2b87b39	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006t-0900000000-3c9902ca237f9c26a2fb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006x-0900000000-dec59115a19fdec78a9f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-c04cbf634e493a774cd5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006t-0900000000-2ea3694383dd21b13356	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-2ffc3da62f3c0184f7c5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-676b079fd7de743702db	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-67a5eac4e8faa4d5cd65	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-b04e175289861dc518f1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006t-0900000000-9ebb090b4661d7668df3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-f2347baf04672bb9e5bb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-9a37bfbb7353bd8bce87	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001j-0900000000-2f420836beda4ff3e6b2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-2275f7938116d06948a0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-2900000000-1f84e054a206191e525d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-e9e614ab5237139c5988	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-0903202525aeeeca151c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00l2-0900000000-ba164ed659e5620dad0a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-d2d648aa4423d0c7a455	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-d2d648aa4423d0c7a455	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014m-0900000000-28208ede76de2a1de764	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-d89ea9976ffd35a15c71	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-d89ea9976ffd35a15c71	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fr-4900000000-898bdc0aea53b4a93d9f	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
370.0 Log mg/kg [210:660]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Tacrine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Overdosage with cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved.

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Health Effects

Health Effect	Relationship	Direction	Description	Reference
Alzheimer's disease	Not Available	Not Available	A neurodegenerative disease which causes neural atrophy, leading to dementia and memory loss.	PMC7474395 , PMC6271686
diarrhea	Associated With?	Not Available	A disorder characterized by an increase in frequency and/or loose or watery bowel movements. (NCI CTCAE)	PMC9143817
nausea	Associated With?	Not Available	A disorder characterized by a queasy sensation and/or the urge to vomit. (NCI CTCAE)	PMC2690856 , PMC6625431
vomiting	Associated With?	Not Available	A disorder characterized by the reflexive act of ejecting the contents of the stomach through the mouth. (NCI CTCAE)	PMC2690856 , PMC6625431
cognitive impairment	Has Therapeutic Effect On	Not Available	Not Available	PMC6359223
memory impairment	Not Available	Not Available	A disorder characterized by a deterioration in memory function. (NCI CTCAE)	PMC3834986
agitation	Associated With?	Not Available	A disorder characterized by a state of restlessness associated with unpleasant feelings of irritability and tension. (NCI CTCAE)	PMC9143817
lupus nephritis	Not Available	Not Available	Not Available	PMC7474395
Poor appetite	Associated With?	Not Available	Not Available	PMC6625431
diarrheal disease	Associated With?	Not Available	Not Available	PMC6625431
Cognitive Dysfunction	Not Available	Not Available	Not Available	PMC3834986
Dyskinesia	Not Available	Not Available	Not Available	PMC7474395
Clumsiness	Associated With?	Not Available	Not Available	PMC6625431

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000380	Anti-dementia drugs?Anti-dementia drugs, primarily used to manage symptoms of cognitive decline in conditions such as Alzheimer's disease, include cholinesterase inhibitors and NMDA receptor antagonists.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000497	Floors?Floors in built environments can be a significant source of synthetic chemical contamination due to the materials and finishes used in their construction.	Building & Construction	PubChem
CEDs000505	Amplifiers?Amplifiers, commonly used in various electronic devices to enhance signal strength, can be a source of synthetic chemical contamination due to the materials and processes involved in their production and disposal.	Electrical & Electronic Equipment	PubChem
CEDs000506	Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.	Electrical & Electronic Equipment	PubChem
CEDs000507	Auxiliary Devices?Auxiliary devices, such as capacitors, transformers, and circuit breakers, are integral components in various electronic systems.	Electrical & Electronic Equipment	PubChem
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000519	Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.	Electrical & Electronic Equipment	PubChem
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	PubChem
CEDs000537	Television Systems?Television systems can be a source of synthetic chemical contamination due to the various materials and components used in their manufacture and operation.	Electrical & Electronic Equipment	PubChem
CEDs000539	Video Games?Video games, through their production and disposal processes, can be a source of synthetic chemical contamination.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000548	Preparation Of Vinegar?Vinegar is produced through the fermentation of ethanol by acetic acid bacteria, resulting in a solution that typically contains 4-8% acetic acid.	Food, food processing & cookware	PubChem
CEDs000549	Preparation Of Wine Or Sparkling Wine?The preparation of wine or sparkling wine involves various stages, including fermentation, aging, and bottling, which can introduce potential sources of synthetic chemical contamination.	Food, food processing & cookware	PubChem
CEDs000551	Processing Fish?Processing fish can lead to synthetic chemical contamination through various stages of production and preservation.	Food, food processing & cookware	PubChem
CEDs000552	Processing Meats?Processing meats can lead to synthetic chemical contamination primarily through the use of additives and preservatives.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	Household cleaning & consumer products	PubChem
CEDs000562	Pipe Accessories?Pipe accessories, such as fittings, connectors, and seals, are components used in plumbing systems to facilitate the flow of liquids and gases.	Household cleaning & consumer products	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000567	Tobacco Product Cases?Tobacco product cases can serve as a source of synthetic chemical contamination due to the presence of various additives and chemicals used in tobacco processing and product manufacturing.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000578	Making Cigars?The process of making cigars involves several steps, including the cultivation of tobacco, fermentation, and the application of various additives to enhance flavor and preservation.	Industrial manufacturing & chemical processing	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000620	Card Games?Card games often utilize synthetic materials for playing cards and associated gaming equipment, which may contain various chemicals such as polyvinyl chloride (PVC), plastics, and dyes.	Recreation & sports surfaces	PubChem
CEDs000630	Toys?Toys, particularly those made from synthetic materials such as plastics, can be a source of chemical contamination due to the presence of various additives and compounds used in their production.	Recreation & sports surfaces	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000634	Buckles?Buckles, commonly used as fasteners in clothing, accessories, and furniture, can be a source of synthetic chemical contamination due to the materials and coatings employed in their production.	Textiles, leather & furnishings	PubChem
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	PubChem
CEDs000643	Headwear?Headwear made from synthetic materials often incorporates chemicals used in the manufacturing and finishing processes, such as dyes, flame retardants, and water repellents.	Textiles, leather & furnishings	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000653	Sewing?Sewing processes often involve the use of various synthetic chemicals, which can become sources of contamination in the environment.	Textiles, leather & furnishings	PubChem
CEDs000658	Touch Fasteners?Touch fasteners, commonly known as hook-and-loop fasteners, are composed of synthetic materials such as nylon or polyester.	Textiles, leather & furnishings	PubChem
CEDs000662	Yarns Or Threads?Yarns or threads used in textiles can be a source of synthetic chemical contamination due to the production processes and treatments they undergo.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	PubChem
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000697	Submarines?Submarines, while essential for military and research purposes, can be a source of synthetic chemical contamination due to their use of various industrial chemicals.	Marine, shipping & aquaculture	PubChem
CEDs000727	Printing Machines Or Presses?Printing machines or presses commonly utilize synthetic chemicals such as inks, solvents, and cleaning agents.	Paper, pulp & fiber products	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

3 pathwaysPathway Source: PathBank

Tacrine Action Pathway (new)

Tacrine Drug Metabolism Action Pathway

Tacrine Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	Prediction Confidence Score 0.456 Applicability Domain 1.0 Statistical Significance 0.0042 Supporting Reference Compounds 793 E-value 32.6967
Click to view 3D structure	Beta-secretase 1	P56817	Humans	Predicted (SEA)	Prediction Confidence Score 0.43 Applicability Domain 0.537 Statistical Significance 0.0036 Supporting Reference Compounds 163 E-value 28.3371
Click to view 3D structure	Glycogen synthase kinase-3 beta	P49841	Humans	Predicted (SEA)	Prediction Confidence Score 0.428 Applicability Domain 1.0 Statistical Significance 0.0134 Supporting Reference Compounds 1157 E-value 104.707
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	Prediction Confidence Score 0.397 Applicability Domain 1.0 Statistical Significance 0.0055 Supporting Reference Compounds 451 E-value 43.0506
Click to view 3D structure	Histamine N-methyltransferase	Q01984	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.396 Applicability Domain 1.0 Statistical Significance 1.70e-04 Supporting Reference Compounds 7 E-value 1.32344
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	Prediction Confidence Score 0.393 Applicability Domain 1.0 Statistical Significance 0.0152 Supporting Reference Compounds 1130 E-value 118.175
Click to view 3D structure	Cannabinoid receptor 2	P34972	Humans	Predicted (SEA)	Prediction Confidence Score 0.388 Applicability Domain 1.0 Statistical Significance 0.0031 Supporting Reference Compounds 175 E-value 23.8219
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	Prediction Confidence Score 0.387 Applicability Domain 1.0 Statistical Significance 0.0032 Supporting Reference Compounds 373 E-value 24.9118
Click to view 3D structure	Amine oxidase [flavin-containing] B	P19643	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.373 Applicability Domain 1.0 Statistical Significance 0.0016 Supporting Reference Compounds 77 E-value 12.6894
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.367 Applicability Domain 1.0 Statistical Significance 0.0076 Supporting Reference Compounds 208 E-value 58.9319
Click to view 3D structure	Cannabinoid receptor 1	P21554	Humans	Predicted (SEA)	Prediction Confidence Score 0.366 Applicability Domain 1.0 Statistical Significance 0.0045 Supporting Reference Compounds 200 E-value 35.2657
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Known	Not Available
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	Prediction Confidence Score 0.9 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 406 E-value 0.155698
Click to view 3D structure	Cholinesterase	P06276	Humans	Predicted (SEA)	Prediction Confidence Score 0.9 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 234 E-value 0.0778492
Click to view 3D structure	Cholinesterase	P81908	Equus caballus	Predicted (SEA)	Prediction Confidence Score 0.894 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 201 E-value 0.0778492
Click to view 3D structure	Acetylcholinesterase	P37136	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.89 Applicability Domain 1.0 Statistical Significance 4.00e-05 Supporting Reference Compounds 95 E-value 0.311397
Click to view 3D structure	Acetylcholinesterase	O42275	Electrophorus electricus	Predicted (SEA)	Prediction Confidence Score 0.818 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 206 E-value 0.0778492
Click to view 3D structure	Norepinephrine transporter	Q9WTR4	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.774 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 112 E-value 0.155698
Click to view 3D structure	Butyrylcholinesterase	Q9N1N9	Equus caballus	Predicted (SEA)	Prediction Confidence Score 0.738 Applicability Domain 1.0 Statistical Significance 9.00e-05 Supporting Reference Compounds 44 E-value 0.700643
Click to view 3D structure	Butyrylcholinesterase	Q9JKC1	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.715 Applicability Domain 1.0 Statistical Significance 1.30e-04 Supporting Reference Compounds 32 E-value 1.01204
Click to view 3D structure	Acetylcholinesterase	P23795	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.715 Applicability Domain 1.0 Statistical Significance 1.20e-04 Supporting Reference Compounds 50 E-value 0.934191
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.688 Applicability Domain 1.0 Statistical Significance 1.80e-04 Supporting Reference Compounds 297 E-value 1.40129
Click to view 3D structure	Acetylcholinesterase	P21836	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.663 Applicability Domain 1.0 Statistical Significance 1.00e-04 Supporting Reference Compounds 58 E-value 0.778492
Click to view 3D structure	Amyloid-beta precursor protein	P05067	Humans	Predicted (SEA)	Prediction Confidence Score 0.547 Applicability Domain 1.0 Statistical Significance 2.70e-04 Supporting Reference Compounds 109 E-value 2.10193
Click to view 3D structure	Cholinesterase	Q03311	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.542 Applicability Domain 1.0 Statistical Significance 2.80e-04 Supporting Reference Compounds 22 E-value 2.17978
Click to view 3D structure	Acetylcholinesterase	P04058	Torpedo californica	Predicted (SEA)	Prediction Confidence Score 0.482 Applicability Domain 1.0 Statistical Significance 4.40e-04 Supporting Reference Compounds 30 E-value 3.42537
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Known	Tacrine acts by elevating acetylcholine concentrations in the cerebral cortex by slowing the degradation of acetylcholine released by still intact cholinergic neurons. It does so by reversibly binding acetylcholinesterase.
Click to view 3D structure	Cholinesterase	P06276	Humans	Known	Not Available
Click to view 3D structure	Acetylcholine receptor subunit epsilon	Q04844	Humans	Known	Not Available
Click to view 3D structure	Cannabinoid receptor 1	P21554	Humans	Known	Not Available
Click to view 3D structure	Cannabinoid receptor 2	P34972	Humans	Known	Not Available
Click to view 3D structure	Cocaine esterase	O00748	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Known	Not Available
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 2A	Q12879	Humans	Known	Not Available
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 2B	Q13224	Humans	Known	Not Available
Click to view 3D structure	Liver carboxylesterase 1	P23141	Humans	Known	Not Available
Click to view 3D structure	Metallothionein-2	P02795	Humans	Known	Not Available
Click to view 3D structure	Multidrug and toxin extrusion protein 1	Q96FL8	Humans	Known	Not Available
Click to view 3D structure	Multidrug and toxin extrusion protein 2	Q86VL8	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Known	Not Available
Click to view 3D structure	Solute carrier family 22 member 1	O15245	Humans	Known	Not Available
Click to view 3D structure	Solute carrier family 22 member 2	O15244	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00382

HMDB ID

HMDB0014526

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

S. Shirley Yang, Wayne Boisvert, Nouman A. Muhammad, Jay Weiss, “Controlled release tacrine drug delivery systems and methods for preparing same.” U.S. Patent US5576022, issued February, 1993.

MSDS

Link

General References

Qizilbash N, Whitehead A, Higgins J, Wilcock G, Schneider L, Farlow M: Cholinesterase inhibition for Alzheimer disease: a meta-analysis of the tacrine trials. Dementia Trialists' Collaboration. JAMA. 1998 Nov 25;280(20):1777-82. [PubMed: 9842955]
Hansen RA, Gartlehner G, Kaufer DJ, Lohr KN, Carey T: [PubMed: 20480924]
Drugs.com - http://www.drugs.com/cons/Tacrine.html
RxList: The Internet Drug Index (2009). - http://www.rxlist.com/

Tacrine (CED0003989)

Structure for CHEM002185: Tacrine

Structure