Raubasine

The Raubasine, with the CAS registry number 483-04-5, is also known as Ajmalicine. It belongs to the product categories of Aromatics; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 207-589-5. This chemical's molecular formula is C₂₁H₂₄N₂O₃ and molecular weight is 352.43. What's more, its systematic name is called Methyl (19α)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate. Raubasine is an antihypertensive drug used in the treatment of high blood pressure. It is also an alkaloid found naturally in various plants.

Physical properties about Raubasine are: (1)ACD/LogP: 2.519; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.08; (4)ACD/LogD (pH 7.4): 1.60; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 5.80; (7)ACD/KOC (pH 5.5): 1.39; (8)ACD/KOC (pH 7.4): 67.05; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 54.56 Å²; (13)Index of Refraction: 1.656; (14)Molar Refractivity: 99.371 cm³; (15)Molar Volume: 270.407 cm³; (16)Polarizability: 39.394×10^-24cm³; (17)Surface Tension: 58.687 dyne/cm; (18)Density: 1.303 g/cm³; (19)Flash Point: 270.731 °C; (20)Enthalpy of Vaporization: 79.785 kJ/mol; (21)Boiling Point: 524.042 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Raubasine: this chemical can be prepared by (16E,19S)-17,19-epoxy-16-methoxycarbonyl-coryna-3,16-dienium; perchlorate. This reaction needs reagent (n-C₄H₉)₃SnH and solvent methanol at ambient temperature. The reaction time is 5 min. The yield is 90 %.

Uses of Raubasine: it is used to produce other chemicals. For example, it can produce (2S,7R)-2,7-dihydroajmalicine. The reaction occurs with reagents trifluoroacetic acid, triethylsilane and the reaction temperature from 0 °C to room temperature. The yield is 85 %.

When you are dealing with this chemical, you should be very careful. This chemical is toxic if swallowed. The gas can not be breathed. In case of accident or if you feel unwell you should seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OC)\C4=C\O[C@H]([C@H]5CN3CCc1c(nc2ccccc12)[C@@H]3C[C@H]45)C
(2) InChI: InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1
(3) InChIKey: GRTOGORTSDXSFK-XJTZBENFSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	oral	12500ug/kg (12.5mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: GENERAL ANESTHETIC	Chest. Vol. 76, Pg. 97, 1979.
guinea pig	LDLo	intravenous	20mg/kg (20mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 600, 1973.
mouse	LD50	intraperitoneal	165mg/kg (165mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 117, 1972.
mouse	LD50	intravenous	20mg/kg (20mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 233, Pg. 72, 1958.
mouse	LD50	oral	400mg/kg (400mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 117, 1972.
rabbit	LD50	intravenous	20mg/kg (20mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 117, 1972.
rabbit	LD50	oral	500mg/kg (500mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 117, 1972.
rat	LD50	intraperitoneal	200mg/kg (200mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 117, 1972.
rat	LD50	intravenous	24mg/kg (24mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 117, 1972.
rat	LDLo	oral	750mg/kg (750mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 233, Pg. 72, 1958.