Rotundine

Modify Date: 2025-08-21 18:10:14

Rotundine structure	Common Name	Rotundine
	CAS Number	483-14-7	Molecular Weight	355.427
	Density	1.2±0.1 g/cm3	Boiling Point	482.9±45.0 °C at 760 mmHg
	Molecular Formula	C₂₁H₂₅NO₄	Melting Point	141-143ºC
	MSDS	USA	Flash Point	138.7±25.9 °C

Use of Rotundine

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.

Name	tetrahydropalmatine
Synonym	More Synonyms

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.

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

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

RIDADR	NONH for all modes of transport
RTECS	HQ1792500

Precursor 9
CAS#:50-00-0 Formaldehyde CAS#:870282-81-8 (13aS)-2,3,9,10... CAS#:870282-77-2 [1-(3,4-dimetho... CAS#:870282-79-4 (3S)-3-(3,4-dim...
CAS#:870282-78-3 (3S)-3-(3,4-dim... CAS#:70945-99-2 N,N-diethyl-2,3... CAS#:120-14-9 veratraldehyde CAS#:870282-80-7 (3S)-2-(2,2-die...
CAS#:870282-71-6 (3S)-2-(2-pheny...
DownStream 1
CAS#:2506-20-9 L-Tetrahydropal...

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

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