Synonym
Noratropine; Norhyoscyamine
IUPAC/Chemical Name
(1R,3r,5S)-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
InChi Key
ATKYNAZQGVYHIB-MCOXGKPRSA-N
InChi Code
InChI=1S/C16H21NO3/c18-10-15(11-4-2-1-3-5-11)16(19)20-14-8-12-6-7-13(9-14)17-12/h1-5,12-15,17-18H,6-10H2/t12-,13+,14+,15?
SMILES Code
O=C(O[C@@H]1C[C@@H](N2)CC[C@@H]2C1)C(CO)C3=CC=CC=C3
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
Shelf Life
>3 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
Biological target:
Noratropine is a metabolite of Atropine (A794625).
Preparing Stock Solutions
The following data is based on the
product
molecular weight
275.35
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 |
Formulation protocol:
TBD
1: NADOR K, GYORGY L, DODA MM. N-Allyl-noratropine. J Med Pharm Chem. 1961 Jan 10;3:183-5. PubMed PMID: 14477808.
2: DECSI L, NADOR K. [The pharmacology of N-allyl-noratropine]. Arzneimittelforschung. 1963 Jul;13:567-71. German. PubMed PMID: 14026357.
3: Van der Meer MJ, Hundt HK. Preparation of noratropine by oxidative n-demethylation of atropine. J Pharm Pharmacol. 1983 Jun;35(6):408. PubMed PMID: 6135792.
4: Van der Meer MJ, Hundt HK, Müller FO. The metabolism of atropine in man. J Pharm Pharmacol. 1986 Oct;38(10):781-4. PubMed PMID: 2879005.
5: Bitar Y, Holzgrabe U. Impurity profiling of atropine sulfate by microemulsion electrokinetic chromatography. J Pharm Biomed Anal. 2007 Jul 27;44(3):623-33. Epub 2006 Sep 12. PubMed PMID: 16971086.
6: Al Balkhi MH, Schiltz S, Lesur D, Lanoue A, Wadouachi A, Boitel-Conti M. Norlittorine and norhyoscyamine identified as products of littorine and hyoscyamine metabolism by (13)C-labeling in Datura innoxia hairy roots. Phytochemistry. 2012 Feb;74:105-14. doi: 10.1016/j.phytochem.2011.10.010. Epub 2011 Nov 13. PubMed PMID: 22083085.
7: Souccar C, Soldera Jdo C, Cysneiros RM, Gonçalo Mdo C, Lapa AJ. Prejunctional effect of quaternary derivatives of l-hyoscyamine at the rat neuromuscular junction. A structure-activity relationship study. Gen Pharmacol. 1994 Nov;25(7):1397-404. PubMed PMID: 7896051.
8: Phillipson JD, Handa SS, Gorrod JW. Metabolic N-oxidation of atropine, hyoscine and the corresponding nor-alkaloids by guinea-pig liver microsomal preparations. J Pharm Pharmacol. 1976 Sep;28(9):687-91. PubMed PMID: 10391.
