(+)-Anabasine hydrochloride

Modify Date: 2024-01-04 17:53:03

(+)-Anabasine hydrochloride Structure
(+)-Anabasine hydrochloride structure
 Common Name (+)-Anabasine hydrochloride
CAS Number 53912-89-3 Molecular Weight 198.69200
Density 1.014g/cm3 Boiling Point 271ºC at 760mmHg
Molecular Formula C10H15ClN2 Melting Point N/A
MSDS N/A Flash Point 93.3ºC
Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08		 Signal Word Danger

 Use of (+)-Anabasine hydrochloride


(+)-Anabasine hydrochloride is an alkaloid found in Nicotiana, and it is a potent nAChR agonist. (+)-Anabasine hydrochloride induces depolarization of TE671 cells endogenously expressing human fetal muscle-type nAChRs with an EC50 of 0.7 µM[1][2].

 Names

Name (S)-1,2,3,4,5,6-Hexahydro-[2,3']bipyridinyl hydrochloride
Synonym More Synonyms

 (+)-Anabasine hydrochloride Biological Activity

Description (+)-Anabasine hydrochloride is an alkaloid found in Nicotiana, and it is a potent nAChR agonist. (+)-Anabasine hydrochloride induces depolarization of TE671 cells endogenously expressing human fetal muscle-type nAChRs with an EC50 of 0.7 µM[1][2].
Related Catalog
Target

nAChR[1]

References

[1]. Green BT, et, al. Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors. Neurotoxicol Teratol. May-Jun 2010; 32(3): 383-90.

[2]. Palmer-Young EC, et, al. Context-dependent medicinal effects of anabasine and infection-dependent toxicity in bumble bees. PLoS One. 2017 Aug 23; 12(8): e0183729.

 Chemical & Physical Properties

Density 1.014g/cm3
Boiling Point 271ºC at 760mmHg
Molecular Formula C10H15ClN2
Molecular Weight 198.69200
Flash Point 93.3ºC
Exact Mass 198.09200
PSA 24.92000
LogP 3.02700
Storage condition Desiccate at RT

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UT7373000
CHEMICAL NAME :
Pyridine, 3-(2-piperidinyl)-, monohydrochloride, (S)-
CAS REGISTRY NUMBER :
53912-89-3
LAST UPDATED :
199403
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C10-H14-N2.Cl-H
MOLECULAR WEIGHT :
198.72

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
235 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 14,407,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
39500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 14,407,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
34100 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 14,407,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
24200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 14,407,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
23 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 14,407,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5180 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 14,407,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
39 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,30,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
247 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 14,407,1989 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
15 mg/kg
SEX/DURATION :
female 4 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 45(1),87,1982 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 0.5 mg/m3 JAN 1993

 Safety Information

Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger
Hazard Statements H225-H301 + H311 + H331-H370
Precautionary Statements P210-P260-P280-P301 + P310-P311
Hazard Codes F,T
Risk Phrases 11-23/24/25-39/23/24/25
Safety Phrases 16-36/37-45
RIDADR UN1230 - class 3 - PG 2 - Methanol, solution

 Synthetic Route

(2R,3S,4S,5R,6R)-2-((pivaloyloxy)methyl)-6-((S)-2-(pyridin-3-yl)piperidin-1-yl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) structure

(2R,3S,4S,5R,6R...

CAS#:121675-95-4

~94%

(+)-Anabasine hydrochloride Structure

(+)-Anabasine h...

CAS#:53912-89-3

2,3,4,6-Tetra-O-pivaloyl-α/β-D-galactopyranose structure

2,3,4,6-Tetra-O...

CAS#:135865-76-8

Literature: Kunz, Horst; Pfrengle, Waldemar Angewandte Chemie, 1989 , vol. 101, # 8 p. 1041 - 1042
(2R,3R,4S,5S,6R)-2-((S)-4-oxo-2-(pyridin-3-yl)piperidin-1-yl)-6-((pivaloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) structure

(2R,3R,4S,5S,6R...

CAS#:121675-93-2

~%

(+)-Anabasine hydrochloride Structure

(+)-Anabasine h...

CAS#:53912-89-3

Literature: Synthesis, , # 10 p. 1151 - 1160
(2R,3S,4S,5R,6R)-2-((pivaloyloxy)methyl)-6-((S)-7-(pyridin-3-yl)-1,4-dithia-8-azaspiro[4.5]decan-8-yl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) structure

(2R,3S,4S,5R,6R...

CAS#:122294-65-9

~%

(+)-Anabasine hydrochloride Structure

(+)-Anabasine h...

CAS#:53912-89-3

Literature: Synthesis, , # 10 p. 1151 - 1160
Anabasine structure

Anabasine

CAS#:494-52-0

~40%

(+)-Anabasine hydrochloride Structure

(+)-Anabasine h...

CAS#:53912-89-3

Literature: Wojciechowska-Nowak, Marzena; Boczon, Wladyslaw; Rychlewska, Urszula; Warzajtis, Beata Journal of Molecular Structure, 2007 , vol. 840, # 1-3 p. 44 - 52
Nicotinaldehyde structure

Nicotinaldehyde

CAS#:500-22-1

~%

(+)-Anabasine hydrochloride Structure

(+)-Anabasine h...

CAS#:53912-89-3

Literature: Angewandte Chemie, , vol. 101, # 8 p. 1041 - 1042
(2R,3S,4S,5R,6R)-2-((pivaloyloxy)methyl)-6-((E)-(pyridin-3-ylmethylene)amino)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) structure

(2R,3S,4S,5R,6R...

CAS#:121675-84-1

~%

(+)-Anabasine hydrochloride Structure

(+)-Anabasine h...

CAS#:53912-89-3

Literature: Angewandte Chemie, , vol. 101, # 8 p. 1041 - 1042
(2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(3-pyridyl)-5,6-didehydro-piperidin-4-one structure

(2S)-N-(2,3,4,6...

CAS#:121675-97-6

~%

(+)-Anabasine hydrochloride Structure

(+)-Anabasine h...

CAS#:53912-89-3

Literature: Angewandte Chemie, , vol. 101, # 8 p. 1041 - 1042
(2R,3S,4S,5R,6R)-2-((pivaloyloxy)methyl)-6-((S)-2-(pyridin-3-yl)piperidin-1-yl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate) structure

(2R,3S,4S,5R,6R...

CAS#:121675-95-4

~%

(+)-Anabasine hydrochloride Structure

(+)-Anabasine h...

CAS#:53912-89-3

Literature: Synthesis, , # 10 p. 1151 - 1160

 Synonyms

Gamibasin
Anabasine monohydrochloride
Anabasin hydrochloride
Anabaside hydrochloride
Anabasin chloride
anabasine hydrochloride
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