Synonym
NSC 145160; NSC145160; NSC-145160; Adamantanine; 2-Aminoadamantane-2-carboxylic acid
IUPAC/Chemical Name
2-Aminoadamantane-2-carboxylic acid
InChi Key
WQMQRNCPZFUGID-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H17NO2/c12-11(10(13)14)8-2-6-1-7(4-8)5-9(11)3-6/h6-9H,1-5,12H2,(H,13,14)
SMILES Code
O=C(C1(N)C2CC3CC(C2)CC1C3)O
Purity
>95% (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
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).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
195.26
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Nagaswa HT, Elberling JA, Shirota FN. 2-Aminoadamantane-2-carboxylic acid, a rigid, achiral, tricyclic alpha-amino acid with transport inhibitory properties. J Med Chem. 1973 Jul;16(7):823-6. doi: 10.1021/jm00265a016. PMID: 4725929.
2: Szcześniak P, Pieczykolan M, Stecko S. The Synthesis of α,α-Disubstituted α-Amino Acids via Ichikawa Rearrangement. J Org Chem. 2016 Feb 5;81(3):1057-74. doi: 10.1021/acs.joc.5b02628. Epub 2016 Jan 12. PMID: 26726732.
3: Mazzier D, Grassi L, Moretto A, Alemán C, Formaggio F, Toniolo C, Crisma M. En route towards the peptide γ-helix: X-ray diffraction analyses and conformational energy calculations of Adm-rich short peptides. J Pept Sci. 2017 Apr;23(4):346-362. doi: 10.1002/psc.2957. Epub 2016 Dec 22. PMID: 28004461.
4: Ingham RJ, Battilocchio C, Fitzpatrick DE, Sliwinski E, Hawkins JM, Ley SV. A systems approach towards an intelligent and self-controlling platform for integrated continuous reaction sequences. Angew Chem Int Ed Engl. 2015 Jan 2;54(1):144-8. doi: 10.1002/anie.201409356. Epub 2014 Nov 5. PMID: 25377747; PMCID: PMC4502965.
5: Battilocchio C, Guetzoyan L, Cervetto C, Di Cesare Mannelli L, Frattaroli D, Baxendale IR, Maura G, Rossi A, Sautebin L, Biava M, Ghelardini C, Marcoli M, Ley SV. Flow Synthesis and Biological Studies of an Analgesic Adamantane Derivative That Inhibits P2X7-Evoked Glutamate Release. ACS Med Chem Lett. 2013 May 22;4(8):704-9. doi: 10.1021/ml400079h. PMID: 24900736; PMCID: PMC4027228.
