Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C7H14NO3.Cl |
| Molecular Weight | 195.644 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].C[N+]1(C)C[C@H](O)C[C@H]1C(O)=O
InChI
InChIKey=GGQVAWGGOKAHNP-IBTYICNHSA-N
InChI=1S/C7H13NO3.ClH/c1-8(2)4-5(9)3-6(8)7(10)11;/h5-6,9H,3-4H2,1-2H3;1H/t5-,6+;/m1./s1
Betonicine (trans-2-carboxy-4-hydroxy-1,1,-dimethylpyrrolidinium hydroxide, inner salt) and its cis isomer, turicine, are naturally occurring substituted pyrrolidines. Betonicine was used as an analgesic 1000 years ago and is still available commercially from herbalists today. Betonicine has been isolated from Achillea millefolium L. (Compositae) and probably from A. atrata L. (Compositae); it is an alkaloid. Proline betaine and Betonicine were identified as metabolically inert cell protectants against extremes in osmolarity and growth temperatures.
Approval Year
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Yarrow (Achillea millefolium) is an extract of the yarrow, A. millefolium, and functions as a biological additive in cosmetic products. Betonicine has been identified as a component of A.millefolium. In 1998, it was reported to the FDA that yarrow (Achillea millefolium) extract was used in 65 cosmetic formulations. In 1984, yarrow extract was reported to be used at concentrations
of ≤ 25%. Submissions from suppliers indicate that yarrow (Achillea millefolium) extract (actual yarrow extract content of
2% to 25%) is used at concentrations of 0.5% to 10%.
The oral and subcutaneous LD50 of yarrow (Achillea millefolium) extract were both 1 g/kg for the mouse. In humans in clinical testing, product formulations containing 0.1% to 0.5% yarrow (Achillea millefolium) extract (2% extract) were
generally not irritating.
Route of Administration:
Other
The chemically-synthesized betonicine dose-dependently stimulated the QS (Quorum sensing) response in a concentration range from 10(−3) to 10(−6) M. When added to 10(−6) M OHL (Noctanoyl-dl-homoserine lactone), betonicine (10(−3) to 10(−6) M) did not improve the OHL-mediated QS stimulation.
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IGV5268VCL
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SUBSTANCE RECORD
