Pachycarpine

Names

[ CAS No. ]:
492-08-0

[ Name ]:
Pachycarpine

[Synonym ]:
[7S-(7a,7aa,14a,14ab)]-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine
[7S-(7α,7aα,14α,14aβ)]-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine
(1S,2R,9S,10S)-7,15-Diazatetracyclo[7.7.1.0.0]heptadecane
Sparteine, (+)-Isomer
lupinidine
sparteine
Pachycarpine
(7α,9α)-Sparteine
7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine, dodecahydro-, (7R,7aR,14R,14aS)-
7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine, dodecahydro-, (7S,7aR,14S,14aS)-

Biological Activity

[Description]:

(+)-Sparteine is a natural alkaloid acting as a ganglionic blocking agent. (+)-Sparteine competitively blocks nicotinic ACh receptor in the neurons.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR

Signaling Pathways >> Neuronal Signaling >> nAChR

Natural Products >> Alkaloid

Research Areas >> Neurological Disease

[Target]

AChR[1]

[In Vitro]

(+)-Sparteine (2 μM) reduces the ACh-induced current caused by activation of nicotinic AChRs in a voltage-independent manner. (+)-Sparteine (5, 10 μM) reduces the amplitude of the excitatory postsynaptic current (EPSC) and the time constant of the EPSC decay[1].

[References]

[1]. Voitenko S, et al. Effect of (+)-sparteine on nicotinic acetylcholine receptors in the neurons of rat superior cervical ganglion. Mol Pharmacol. 1991 Aug;40(2):180-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
340.9±10.0 °C at 760 mmHg

[ Melting Point ]:
201ºC

[ Molecular Formula ]:
C₁₅H₂₆N₂

[ Molecular Weight ]:
234.380

[ Flash Point ]:
148.3±6.8 °C

[ Exact Mass ]:
234.209595

[ PSA ]:
6.48000

[ LogP ]:
3.21

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.570

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RT0620000

CHEMICAL NAME :: Pachycarpine

CAS REGISTRY NUMBER :: 492-08-0

BEILSTEIN REFERENCE NO. :: 3540601

LAST UPDATED :: 199709

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C15-H26-N2

MOLECULAR WEIGHT :: 234.43

WISWESSER LINE NOTATION :: T C66 K66 A HN PNTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 89100 ug/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: SHIYDO Shaanxi Xinyiyao. Shaanxi New Medical. (Shaanxi Renmin Chubanshe, Xi'an, Shaanxi, Peop. Rep. China) V.1- 1972- Volume(issue)/page/year: 11(6),53,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 90 mg/kg

TOXIC EFFECTS :: Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - dyspnea

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: 21(5),46,1958

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 26 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 32ZCAI "Ganglion-Blocking and Ganglion-Stimulation Agents," Kharkevich, D.A., Moscow, First Moscow Medical Institute, 1967 Volume(issue)/page/year: -,175,1967

Safety Information

[ Hazard Codes ]:
Xi

[ RTECS ]:
RT0620000