(S)-(-)-Stepholidine

Names

[ Name ]:
(S)-(-)-Stepholidine

[Synonym ]:
(13aS)-3,9-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,10-diol
(13aS)-3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol
(-)-Stepholidine
6H-Dibenzo[a,g]quinolizine-2,10-diol, 5,8,13,13a-tetrahydro-3,9-dimethoxy-, (13aS)-
(S)-3,9-Dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,10-diol
(13aS)-3,9-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-2,10-diol
L-Stepholidine
Stepholidine

Biological Activity

[Description]:

L-Stepholidine (Stepholidine), an alkaloid extract of the Chinese herb Stephania intermedia, is the first compound known to exhibit mixed dopamine D1 receptor agonist/D2 antagonist properties. L-Stepholidine (Stepholidine) has neuroprotective effect and inhibits heroin-induced reinstatement. L-Stepholidine (Stepholidine) is a potential medication for the treatment of opiate addiction[1][2][3].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Research Areas >> Neurological Disease

[Target]

Dopamine D1 receptor[1] Dopamine D2 receptor[1]

[References]

[1]. Ma B, et al. L-stepholidine, a natural dopamine receptor D1 agonist and D2 antagonist, inhibits heroin-induced reinstatement. Neurosci Lett. 2014 Jan 24;559:67-71.

[2]. Zhou M, et al. The Neuroprotective Effect of L-Stepholidine on Methamphetamine-Induced Memory Deficits in Mice. Neurotox Res. 2019 Aug;36(2):376-386.

[3]. Wang W, et al. The effect of L-stepholidine, a novel extract of Chinese herb, on the acquisition, expression, maintenance, and re-acquisition of morphine conditioned place preference in rats. Neuropharmacology. 2007 Feb;52(2):355-61. Epub 2006 Oct 5.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
524.0±50.0 °C at 760 mmHg

[ Melting Point ]:
120-122ºC

[ Molecular Formula ]:
C₁₉H₂₁NO₄

[ Molecular Weight ]:
327.374

[ Flash Point ]:
270.7±30.1 °C

[ Exact Mass ]:
327.147064

[ PSA ]:
62.16000

[ LogP ]:
2.16

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.680

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DR9823500

CHEMICAL NAME :: 13a-alpha-Berbine-2,10-diol, 3,9-dimethoxy-

CAS REGISTRY NUMBER :: 16562-13-3

LAST UPDATED :: 198707

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C19-H21-N-O4

MOLECULAR WEIGHT :: 327.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 928 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 6,156,1985

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 358 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 7,522,1986

Safety Information

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%