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Rotundine

Names

[ CAS No. ]:
483-14-7

[ Name ]:
Rotundine

[Synonym ]:
6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (13aS)-
Berberine,tetrahydro
d,l-tetrahydropalmatine
(S)-tetrahydropalmatine
(13aS)-2,3,9,10-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline
Tetrahydropalmatine
Rotundine
(13aS)-2,3,9,10-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline
dl-Canadine
TETRAHYDROPALMATINE, L-(P)
l-Tetrahydropalmatine
(-)-Tetrahydropalmatine
2,3-methylenedioxy-9,10-dimethoxytetrahydroprotoberberine
Canadine dl-form
Canadin
tetrahydropulmatine

Biological Activity

[Description]:

Rotundine is an antagonist of dopamine D1, D2 and D3 receptors with IC50s of 166 nM, 1.4 μM and 3.3 μM, respectively. Rotundine is also an antagonist of 5-HT1A with an IC50 of 370 nM.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor
Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor
Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor
Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor
Natural Products >> Alkaloid
Research Areas >> Neurological Disease

[Target]

IC50: 166 nM (D1 receptor), 1.4 μM (D2 receptor), 3.3 μM (D3 receptor), 370 nM (5-HT1A)[1]


[In Vivo]

It is reported that Rotundine (l-THP) possesses a blocking effect on dopamine D1 and D2 receptors and can inhibit physical dependence in morphine dependent mice and significantly reduce the development of the conditional place preference induced by morphine in mice. On day 1 and 7, there is no difference in locomotor counts between the Rotundine groups (6.25, 12.5, and 18.75 mg/kg) and saline group [F(3, 37)=1.360, P>0.05, F(3, 37)=0.348, P>0.05, respectively]. Locomotor counts are greatly increased in the oxycodone group compare with the saline group. Rotundine at doses of 6.25, 12.5, and 18.75 mg/kg antagonizes hyperactivity induced by oxycodone [F(4, 60)=15.76, P<0.01]. Rotundine (6.25, 12.5 mg/kg) does not affect the magnitude of sensitization, but there is a marked difference between oxycodone+oxycodone group and Rotundine (18.75 mg/kg)+oxycodone+oxycodone group, indicating that Rotundine (18.75 mg/kg) greatly inhibits the development of oxycodone sensitization [F(4, 62)=8.766, P<0.01][2].

[Animal admin]

Kunming mice, initially weighing 18 to 22 g are used in this study. Four groups of mice are given Rotundine (l-THP) (6.25, 12.5, and 18.75 mg/kg) or saline, respectively, once per day for 7 consecutive days, followed by a 5 d withdrawal period. On d 13, all animals are challenged with saline. On day 1, 7, and 13, after 40-min treatment with Rotundine or saline, the mice are put into the test boxes and locomotor activity is monitored for 60 min[2].

[References]

[1]. Wang JB, et al. l-tetrahydropalamatine: a potential new medication for the treatment of cocaine addiction. Future Med Chem. 2012 Feb;4(2):177-86.

[2]. Liu YL, et al. Effects of l-tetrahydropalmatine on locomotor sensitization to oxycodone in mice. Acta Pharmacol Sin. 2005 May;26(5):533-8.


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Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
482.9±45.0 °C at 760 mmHg

[ Melting Point ]:
141-143ºC

[ Molecular Formula ]:
C21H25NO4

[ Molecular Weight ]:
355.427

[ Flash Point ]:
138.7±25.9 °C

[ Exact Mass ]:
355.178345

[ PSA ]:
40.16000

[ LogP ]:
3.70

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.609

[ Storage condition ]:
Refrigerator

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HQ1792500
CHEMICAL NAME :
6H-Dibenzo(a,g)quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (S)-
CAS REGISTRY NUMBER :
483-14-7
LAST UPDATED :
199309
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C21-H25-N-O4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. (Washington, DC) Volume(issue)/page/year: 5,17,1953

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
HQ1792500

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds