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1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE

CAS No.321-64-2
Chemical Name:1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE
CBNumber:CB7699634
Molecular Formula:C13H14N2
Formula Weight:198.26
MOL File:321-64-2.mol

1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE Property

Melting point 183.5℃
Boiling point 325.59°C (rough estimate)
Density 0.9827 (rough estimate)
refractive index 1.4400 (estimate)
storage temp. 4°C, away from moisture and light
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka 9?+-.0.20(Predicted)
color White to Pale Yellow
CAS DataBase Reference 321-64-2(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 4VX7YNB537

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H301+H311+H331-H315-H319
Precautionary statements P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405

1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE Chemical Properties,Usage,Production

Description In the 1950s, tacrine was used experimentally to reverse cholinergic coma in animals. In the 1960s, tacrine was used to reverse the effects of phencyclidine-like drugs. It was also marketed for many years as a respiratory stimulant. In 1993, the US Food and Drug Administration approved tacrine for the treatment of symptoms of mild to moderate Alzheimer’s disease.
Uses The current use of tacrine is limited due to its poor oral bioavailability, the necessity for four daily doses, and serious side effects (including nausea, vomiting, dry mouth, indigestion, diarrhea, loss of appetite, urinary incontinence, collapse, convulsions, and hepatotoxicity). Currently, newer cholinesterase inhibitors (such as donepezil, rivastigmine, and galantamine) are preferred over tacrine.
Definition ChEBI: Tacrine is a member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is a member of acridines and an aromatic amine. It is a conjugate base of a tacrine(1+).
Synthesis Reference(s) Tetrahedron Letters, 4, p. 1277, 1963 DOI: 10.1039/jr9630005127
Toxicity evaluation Tacrine has numerous mechanisms of action. The putative principal mechanism of action of tacrine for Alzheimer’s disease is reversible inhibition of acetylcholinesterase (AChE), which thereby slows the breakdown of the chemical messenger acetylcholine (ACh) in the brain. Tacrine also inhibits butyrylcholinesterase activity. In addition, tacrine blocks sodium and potassium channels. Tacrine also acts as a histamine N-methyltransferase inhibitor.
At a therapeutic dose, tacrine causes liver toxicity. Cytotoxicity studies using the human liver cell line HepG2 showed that a therapeutic blood concentration of tacrine induces reactive oxygen species production and glutathione depletion, suggesting that oxidative stress might be involved in tacrine hepatotoxicity.