BETONICINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C7H13NO3
Molecular Weight	159.183
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[N+]1(C)C[C@H](O)C[C@H]1C([O-])=O

InChI

InChIKey=MUNWAHDYFVYIKH-RITPCOANSA-N

InChI=1S/C7H13NO3/c1-8(2)4-5(9)3-6(8)7(10)11/h5-6,9H,3-4H2,1-2H3/t5-,6+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C7H13NO3
Molecular Weight	159.183
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.google.com/patents/US5622944 | https://www.openaccessgovernment.org/plants-drugs-heterocyclic-chemistry/11053/ | https://books.google.ru/books?id=ry11ai2iPS0C&pg=PA28&lpg=PA28&dq=stimulant+Betonicine retrieved from The Alkaloids: Chemistry and Pharmacology, p.277 | https://www.ncbi.nlm.nih.gov/pubmed/25012968

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
quorum sensing 2 Target ID: GO:0009372 Sources: https://link.springer.com/article/10.1007/s12257-008-0145-x	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine 103 Sources: Mount, T. (2015) Dragon's Blood & Willow Bark: The Mysteries of Medieval Medicine, retrieved from: https://books.google.ru/books?id=UlVpCAAAQBAJ https://materiamedicaresource.wordpress.com/category/circulatory-stimulant/	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Discovery of new enzymes and metabolic pathways by using structure and genome context.	2013 Oct 31	24056934
Sinorhizobium meliloti chemotaxis to quaternary ammonium compounds is mediated by the chemoreceptor McpX.	2017 Jan	27748981

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:09:10 GMT 2023` Edited by `admin` on `Fri Dec 15 19:09:10 GMT 2023`
Record UNII	FBA654632Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BETONICINE

Common Name

English

ACHILLEIN

Common Name

English

PYRROLIDINIUM, 2-CARBOXY-4-HYDROXY-1,1-DIMETHYL-, INNER SALT, (2S-TRANS)-

Systematic Name

English

2-CARBOXY-4-HYDROXY-1,1-DIMETHYLPYRROLIDINIUM HYDROXIDE, INNER SALT, L-TRANS-

Systematic Name

English

(2S-TRANS)-2-CARBOXYLATO-4-HYDROXY-1,1-DIMETHYLPYRROLIDINIUM

Systematic Name

English

4-HYDROXYPROLINE BETAINE, TRANS-

Systematic Name

English

ACHILLEINE

Common Name

English

BETONICINE [MI]

Common Name

English

PYRROLIDINIUM, 2-CARBOXY-4-HYDROXY-1,1-DIMETHYL-, HYDROXIDE, INNER SALT, (2S-TRANS)-

Systematic Name

English

PYRROLIDINIUM, 2-CARBOXY-4-HYDROXY-1,1-DIMETHYL-, INNER SALT, (2S,4R)-

Systematic Name

English

NSC-655264

Code

English

BETONICIN

Common Name

English

Code System Code Type Description

FDA UNII

FBA654632Q