Tacrine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318785

CAS#: 321-64-2

Description: Tacrine is a centrally acting anticholinesterase and indirect cholinergic agonist. It is approved for the treatment of Alzheimer's disease.


Price and Availability

Size
Price

Size
Price

Size
Price

Tacrine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide).


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 318785
Name: Tacrine
CAS#: 321-64-2
Chemical Formula: C13H14N2
Exact Mass: 198.1157
Molecular Weight: 198.269
Elemental Analysis: C, 78.75; H, 7.12; N, 14.13


Synonym: CS 12602, CS 12602, CS 12602, Tacrine, Tacrinum, Tetrahydroaminocrine

IUPAC/Chemical Name: 1,2,3,4-tetrahydroacridin-9-amine

InChi Key: YLJREFDVOIBQDA-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: NC1=C(CCCC2)C2=NC3=CC=CC=C31


Technical Data

Appearance:
White to off-white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Ismaili L, Refouvelet B, Benchekroun M, Brogi S, Brindisi M, Gemma S, Campiani G, Filipic S, Agbaba D, Esteban G, Unzeta M, Nikolic K, Butini S, Marco-Contelles J. Multitarget compounds bearing tacrine- and donepezil-like structural and functional motifs for the potential treatment of Alzheimer's disease. Prog Neurobiol. 2016 Jan 18. pii: S0301-0082(15)00162-8. doi: 10.1016/j.pneurobio.2015.12.003. [Epub ahead of print] Review. PubMed PMID: 26797191.

2: Minarini A, Milelli A, Simoni E, Rosini M, Bolognesi ML, Marchetti C, Tumiatti V. Multifunctional tacrine derivatives in Alzheimer's disease. Curr Top Med Chem. 2013;13(15):1771-86. Review. PubMed PMID: 23931443.

3: Romero A, Cacabelos R, Oset-Gasque MJ, Samadi A, Marco-Contelles J. Novel tacrine-related drugs as potential candidates for the treatment of Alzheimer's disease. Bioorg Med Chem Lett. 2013 Apr 1;23(7):1916-22. doi: 10.1016/j.bmcl.2013.02.017. Epub 2013 Feb 16. Review. PubMed PMID: 23481643.

4: Korábečný J, Spilovská K, Benek O, Musílek K, Soukup O, Kuča K. [Tacrine and its derivatives in the therapy of Alzheimers disease]. Ceska Slov Farm. 2012 Oct;61(5):210-21. Review. Czech. PubMed PMID: 23256654.

5: de Aquino RA, Modolo LV, Alves RB, de Fatima A. Design of new drugs for the treatment of Alzheimer's disease based on tacrine structure. Curr Drug Targets. 2013 Mar;14(3):378-97. Review. PubMed PMID: 23176115.

6: Tumiatti V, Minarini A, Bolognesi ML, Milelli A, Rosini M, Melchiorre C. Tacrine derivatives and Alzheimer's disease. Curr Med Chem. 2010;17(17):1825-38. Review. PubMed PMID: 20345341.

7: Jogani VV, Shah PJ, Mishra P, Mishra AK, Misra AR. Intranasal mucoadhesive microemulsion of tacrine to improve brain targeting. Alzheimer Dis Assoc Disord. 2008 Apr-Jun;22(2):116-24. doi: 10.1097/WAD.0b013e318157205b. Review. PubMed PMID: 18525282.

8: Patocka J, Jun D, Kuca K. Possible role of hydroxylated metabolites of tacrine in drug toxicity and therapy of Alzheimer's disease. Curr Drug Metab. 2008 May;9(4):332-5. Review. PubMed PMID: 18473751.

9: Li WM, Kan KK, Carlier PR, Pang YP, Han YF. East meets West in the search for Alzheimer's therapeutics - novel dimeric inhibitors from tacrine and huperzine A. Curr Alzheimer Res. 2007 Sep;4(4):386-96. Review. PubMed PMID: 17908041.

10: Qizilbash N, Birks J, Lopez Arrieta J, Lewington S, Szeto S. WITHDRAWN: Tacrine for Alzheimer's disease. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD000202. Review. PubMed PMID: 17636619.

11: Summers WK. Tacrine, and Alzheimer's treatments. J Alzheimers Dis. 2006;9(3 Suppl):439-45. Review. PubMed PMID: 16914883.

12: Arrieta JL, Artalejo FR. Methodology, results and quality of clinical trials of tacrine in the treatment of Alzheimer's disease: a systematic review of the literature. Age Ageing. 1998 Mar;27(2):161-79. Review. PubMed PMID: 16296676.

13: Camps P, Muñoz-Torrero D. Tacrine-huperzine A hybrids (huprines): a new class of highly potent and selective acetylcholinesterase inhibitors of interest for the treatment of Alzheimer's disease. Mini Rev Med Chem. 2001 Jul;1(2):163-74. Review. PubMed PMID: 12369981.

14: Qizilbash N, Birks J, Lopez Arrieta J, Lewington S, Szeto S. Tacrine for Alzheimer's disease. Cochrane Database Syst Rev. 2000;(3):CD000202. Review. Update in: Cochrane Database Syst Rev. 2007;(3):CD000202. PubMed PMID: 10908463.

15: Qizilbash N, Birks J, López-Arrieta J, Lewington S, Szeto S. Tacrine for Alzheimer's disease. Cochrane Database Syst Rev. 2000;(2):CD000202. Review. Update in: Cochrane Database Syst Rev. 2000;(3):CD000202. PubMed PMID: 10796507.

16: Proctor GR, Harvey AL. Synthesis of tacrine analogues and their structure-activity relationships. Curr Med Chem. 2000 Mar;7(3):295-302. Review. PubMed PMID: 10637366.

17: Kurz A. The therapeutic potential of tacrine. J Neural Transm Suppl. 1998;54:295-9. Review. PubMed PMID: 9850938.

18: Giacobini E. Invited review: Cholinesterase inhibitors for Alzheimer's disease therapy: from tacrine to future applications. Neurochem Int. 1998 May-Jun;32(5-6):413-9. Review. PubMed PMID: 9676739.

19: Conway EL. A review of the randomized controlled trials of tacrine in the treatment of Alzheimer's disease: methodologic considerations. Clin Neuropharmacol. 1998 Jan-Feb;21(1):8-17. Review. PubMed PMID: 9579280.

20: Ventura M, Sternon J. [Therapeutic results: tacrine]. Rev Med Brux. 1997 Dec;18(6):394-7. Review. French. PubMed PMID: 9481161.