| Identification | More | [Name]
TACRINE HYDROCHLORIDE | [CAS]
1684-40-8 | [Synonyms]
1,2,3,4-TETRAHYDRO-5-AMINOACRIDINE HYDROCHLORIDE
1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE, MONOHYDROCHLORIDE
9-AMINO-1,2,3,4-TETRAHYDROACRIDINE HYDROCHLORIDE
COGNEX
ROMOTAL
TACRINE
TACRINE HCL
TACRINE HYDROCHLORIDE
1,2,3,4-tetrahydro-9-acridinaminmonohydrochloride
1,2,3,4-tetrahydro-9-aminoacridinehydrochloride
1,2,3,4-tetrahydro-9-amino-acridinmonohydrochloride
9-amino-1,2,3,4-tetrahydro-acridinhydrochloride
ci970
hydroaminacrine
tacrinhydrochloride
tenakrin
tetrahydroaminacrin
1,2,3,4-tetrahydroacridin-9-amine monohydrochloride
9-AMINO-1,2,3,4-TETRAHYDROACRIDINEHYDROC HLORIDE HY
9-AMINO-1,2,3,4-TETRAHYDROACRIDINE HYDRO-CHLORIDE (TACRINE, TH | [EINECS(EC#)]
216-867-5 | [Molecular Formula]
C13H15ClN2 | [MDL Number]
MFCD00012657 | [Molecular Weight]
234.72 | [MOL File]
1684-40-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale Yellow Solid | [Melting point ]
280-284 °C(lit.) | [storage temp. ]
2-8°C
| [solubility ]
Soluble in aqueous buffers | [form ]
Crystalline solid | [pka]
pKa 9.8 (Uncertain) | [color ]
White to light yellow | [Usage]
A potent centrally acting anticholinesterase, for therapy of memory deficits in patients with Alzheimers disease. THA also selectively blocks potassium channels in the central nervous system, which results in an increased release of acetylcholi | [InChI]
InChI=1S/C13H14N2.ClH/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);1H | [InChIKey]
ZUFVXZVXEJHHBN-UHFFFAOYSA-N | [SMILES]
C12=CC=CC=C1C(N)=C1CCCCC1=N2.Cl | [CAS DataBase Reference]
1684-40-8(CAS DataBase Reference) | [EPA Substance Registry System]
Tacrine hydrochloride (1684-40-8) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xn | [Risk Statements ]
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/22:Harmful by inhalation and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
AR9532500
| [HazardClass ]
6.1(a) | [PackingGroup ]
II | [Toxicity]
LD50 intravenous in mouse: 5600ug/kg |
| Hazard Information | Back Directory | [General Description]
Yellow needles (from concentrated hydrochloric acid); white powder. pH of 1.5% solution: 4.5-6. Bitter taste. | [Reactivity Profile]
1,2,3,4-TETRAHYDRO-9-AMINOACRIDINE HYDROCHLORIDE MONOHYDRATE(1684-40-8) is incompatible with strong oxidizing agents, acid chlorides and acid anhydrides . Neutralize bases in slightly exothermic reactions. | [Air & Water Reactions]
Water soluble. | [Fire Hazard]
Flash point data for this chemical are not available; however, 1,2,3,4-TETRAHYDRO-9-AMINOACRIDINE HYDROCHLORIDE MONOHYDRATE is probably combustible. | [Description]
Tacrine is a derivative of aminoacridine that functions as an inhibitor of both acetylcholinesterase (AChE) and butyrylcholinesterase (IC50s = 31 and 26.5 nM, respectively).1,2 Tacrine also inhibits the uptake of serotonin and norepinephrine in rat cerebral cortex and decreases depolarization-induced calcium influx through L-type calcium channels in SN56 neuronal cells.3,4,5 Formulations containing tacrine have been used clinically in the treatment of Alzheimer’s disease.3,6 | [Description]
Tacrine 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 acetylcholinesterase inhibitor that presumably acts centrally by elevating the
acetylcholine level in the cerebral cortex and by slowing degradation of acetylcholine from
intact cholinergic neurons. While tacrine improves the symptoms of Alzheimer's disease, the
underlining cause of the dementing process is not altered. It has also been suggested that the
beneficial effects of tacrine may be due to its multiple effects on several neurotransmitter
systems. | [Chemical Properties]
Pale Yellow Solid | [Originator]
NIH (U.S.A.) | [Uses]
A potent centrally acting anticholinesterase for therapy of memory deficits in patients with Alzheimer's disease. THA also selectively blocks potassium channels in the central nervous system, which results in an increased release of acetylcholine and a prolongation of the action potential of the presynaptic cholinergic neurons. | [Uses]
A potent centrally acting anticholinesterase, for therapy of memory deficits in patients with Alzheimers disease. THA also selectively blocks potassium channels in the central nervous system, which results in an increased release of acetylcholi | [Uses]
anticholinesterase, cognitive adjuvant, K channel blocker | [Brand name]
Cognex (Sciele). | [Biological Activity]
Potent cholinesterase inhibitor, a cognition enhancer in vivo . | [Metabolism]
Tacrine is
extensively metabolized by CYP450 to at least three metabolites. The major metabolite, 1-hydroxy-tacrine, is active. Its elimination half-life is
between 1.5 and 4 hours, with metabolites being are excreted via the urine. | [References]
[1] CRISMON M L. Pharmacokinetics and drug interactions of cholinesterase inhibitors administered in Alzheimer’s disease.[J]. Pharmacotherapy, 1998, 18 2 Pt 2: 47-54; discussion 79-82.
[2] MUSHTAQ AHMED. Inhibition of two different cholinesterases by tacrine[J]. Chemico-Biological Interactions, 2006, 162 2: Pages 165-171. DOI: 10.1016/j.cbi.2006.06.002
[3] B. DRUKARCH J. C S J E Leysen. Further analysis of the neuropharmacological profile of 9-amino-1,2,3,4-tetrahydroacridine (THA), an alleged drug for the treatment of Alzheimer’s disease[J]. Life sciences, 1988, 42 9: Pages 1011-1017. DOI: 10.1016/0024-3205(88)90431-6
[4] MAUREEN T. MCKENNA. Novel Tacrine Analogues for Potential Use against Alzheimer’s Disease: Potent and Selective Acetylcholinesterase Inhibitors and 5-HT Uptake Inhibitors[J]. Journal of Medicinal Chemistry, 1997, 40 22: 3516-3523. DOI: 10.1021/jm970150t
[5] VLADIMI?R DOLE?AL Stanislav T Věra Lisá. Effect of tacrine on intracellular calcium in cholinergic SN56 neuronal cells[J]. Brain Research, 1997, 769 2: Pages 219-224. DOI: 10.1016/s0006-8993(97)00711-7
[6] GIACOBINI E. Invited Review Cholinesterase inhibitors for Alzheimer’s disease therapy: from tacrine to future applications[J]. Neurochemistry international, 1998, 32 5: Pages 413-419. DOI: 10.1016/s0197-0186(97)00124-1
[7] GARY TIN. Tricyclic phenothiazine and phenoselenazine derivatives as potential multi-targeting agents to treat Alzheimer’s disease[J]. MedChemComm, 2015, 6 1: 1930-1941. DOI: 10.1039/c5md00274e |
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