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Tacrine hydrochloride

Tacrine hydrochloride structure

CAS No:
1684-40-8
Formula:
C13H14N2.ClH
Chemical Name:
Tacrine hydrochloride
Synonyms:
9-Acridinamine,1,2,3,4-tetrahydro-,hydrochloride (1:1);Acridine,9-amino-1,2,3,4-tetrahydro-,monohydrochloride;9-Acridinamine,1,2,3,4-tetrahydro-,monohydrochloride;Acridine,9-amino-1,2,3,4-tetrahydro-,hydrochloride;Hydroaminacrine;Tacrin hydrochloride;Romotal;Tenakrin;THA;Tacrine hydrochloride;1,2,3,4-Tetrahydro-9-aminoacridine hydrochloride;CI 970;Cognex;9-Amino-1,2,3,4-Tetrahydroacridine hydrochloride;5,6,7,8-Tetrahydroacridin-9-amine hydrochloride;33376-89-5
Categories:
Active Pharmaceutical Ingredients > Specialty Drugs

Description

Pale Yellow SolidTacrine is the first therapeutic launched specifically for the treatment of Alzheimer's disease which affects four million people in the US alone. Clinically significant improvement in cognition has been demonstrated in the patients with Alzheimer's disease. Although the cause of Alzheimer's disease is not understood, degeneration of cholinergic neurons is thought to be a primary factor in the development and progression of the disease. Tacrine is a reversible acetylcholin

1,2,3,4-tetrahydro-9-aminoacridine hydrochloride monohydrate appears as yellow needles (from concentrated hydrochloric acid); white powder. pH of 1.5% solution: 4.5-6. Bitter taste. (NTP, 1992)

1,2,3,4-tetrahydro-9-aminoacridine hydrochloride monohydrate appears as yellow needles (from concentrated hydrochloric acid); white powder. pH of 1.5% solution: 4.5-6. Bitter taste. (NTP, 1992)|Tacrine Hydrochloride is the hydrochloride salt form of tacrine, an aminoacridine derivative with cognitive stimulating property. Although the mechanism of action has not been fully elucidated, tacrine hydrochloride may bind reversibly to cholinesterase, acetylcholinesterase as well as butyrylcholinesterase, thereby decreasing the breakdown of acetylcholine, and prolonging synaptic actions as well as increased release of acetylcholine. In addition, this agent inhibits monoamine oxidase (MAO) and may inhibit the reuptake of catecholamines and serotonin. Finally, a novel mechanism of action studied in animal models suggests tacrine to attenuate the production of interleukin-1beta in the hippocampus and blood, thereby producing central and peripheral anti-inflammatory effects that may play a role in Alzheimer's disease.|A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.

Tacrine hydrochloride Basic Attributes

Molecular Weight：

234.72

Exact Mass：

270.113495

EC Number：

216-867-5

UNII：

4966RNG0BU

NSC Number：

759324|72108

DSSTox ID：

DTXSID1026112

NCI Thesaurus Code：

C47742

HScode：

2933990090

Characteristics

PSA：

38.9

Appearance：

1,2,3,4-tetrahydro-9-aminoacridine hydrochloride monohydrate appears as yellow needles (from concentrated hydrochloric acid); white powder. pH of 1.5% solution: 4.5-6. Bitter taste. (NTP, 1992)

Melting Point：

283-284 °C

Boiling Point：

409.4°C at 760 mmHg

Flash Point：

230.5ºC

Water Solubility：

Soluble in aqueous buffers

Storage Conditions：

2-8°C

Toxicity：

LD50 intravenous in mouse: 5600ug/kg

Collision Cross Section：

141.4 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Air and Water Reactions：

Water soluble.

Reactive Group：

Salts, Acidic

Reactivity Profile：

1,2,3,4-TETRAHYDRO-9-AMINOACRIDINE HYDROCHLORIDE MONOHYDRATE is incompatible with strong oxidizing agents, acid chlorides and acid anhydrides (NTP, 1992). Neutralize bases in slightly exothermic reactions.

Safety Information

Packing level：

Hazard category：

6.1(a)

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

25-36/37/38-20/22

safety instructions：

26-36-45

RTECS Number：

AR9532500

Marks：

T,Xn

Precautionary statement(s)：

Missing Phrase - N15.00950417-P305 + P351 + P338

Hazard Statements：

H301-H315-H319-H335

Fire Hazards：

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fire Fighting：

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Nonfire Spill Response：

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and keep it away from oxidizing materials. (NTP, 1992)

Personal Protective Equipment：

RECOMMENDED RESPIRATOR: Where the neat test chemical is stored, weighed and diluted, wear an approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Drug Information

MeSH：

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)|Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)|Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)

Health Hazards：

SYMPTOMS: Symptoms of exposure to this compound include nausea and vomiting. In conjunction with suxamethonium, it causes prolonged respiratory depression. It is a stimulant of the central nervous system and respiratory system. It may cause irritation of the skin, eyes, mucous membranes and upper respiratory tract. It is a cholinesterase inhibitor. ACUTE/CHRONIC HAZARDS: This chemical may be harmful by inhalation, ingestion or skin absorption. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide, nitrogen oxides and hydrogen chloride gas. It is a CHOLINESTERASE INHIBITOR. (NTP, 1992)

First Aid：

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, administer a slurry of activated charcoal in water and simultaneously call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

MeSH Entry Terms：

1,2,3,4-Tetrahydro-9-acridinamine

Tacrine hydrochloride Use and Manufacturing

Uses

A potent centrally acting anticholinesterase, for therapy of memory deficits in patientswith Alzheimers disease.THA also selectively blocks potassium channels in the centralnervous system, which results in an increased release of acetylcholi

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:234.72
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:234.0923762
Monoisotopic Mass:234.0923762
Topological Polar Surface Area:38.9
Heavy Atom Count:16
Complexity:229
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes