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reserpine
Conditions | Yield |
---|---|
With acetic acid; zinc |
reserpine
Conditions | Yield |
---|---|
With perchloric acid; zinc |
Conditions | Yield |
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With acetic acid; zinc for 12h; Heating; | A 195 mg B 70 mg C 22 mg |
Conditions | Yield |
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With dmap; triethylamine In dichloromethane Ambient temperature; Yield given; | |
With pyridine at 20℃; for 96h; |
reserpine
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid |
(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-7-hydroxymethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester
reserpine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating 2: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C 3: Ag2O; CaSO4 / 20 h 4: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 5: MgSO4 / acetonitrile / 1 h 6: aq. HCl / tetrahydrofuran / 30 h / 20 °C 7: pyridine / 96 h / 20 °C View Scheme |
(1R,5S,6S,7R,9S)-7-Methoxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester
reserpine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 2: MgSO4 / acetonitrile / 1 h 3: aq. HCl / tetrahydrofuran / 30 h / 20 °C 4: pyridine / 96 h / 20 °C View Scheme |
reserpine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: MgSO4 / acetonitrile / 1 h 2: aq. HCl / tetrahydrofuran / 30 h / 20 °C 3: pyridine / 96 h / 20 °C View Scheme |
reserpine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: Ag2O; CaSO4 / 20 h 2: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 3: MgSO4 / acetonitrile / 1 h 4: aq. HCl / tetrahydrofuran / 30 h / 20 °C 5: pyridine / 96 h / 20 °C View Scheme |
reserpine
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: H2 / Pd/C / ethyl acetate / 30 h / 760 Torr 2: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating 3: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C 4: Ag2O; CaSO4 / 20 h 5: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 6: MgSO4 / acetonitrile / 1 h 7: aq. HCl / tetrahydrofuran / 30 h / 20 °C 8: pyridine / 96 h / 20 °C View Scheme |
The Reserpine, with the CAS registry number 50-55-5, is also known as Methyl 18b-Hydroxy-11,17a-dimethoxy-3b,20a-yohimban-16b-carboxylate 3,4,5-Trimethoxybenzoate. It belongs to the product categories of Miscellaneous Natural Products; Alkaloids; Biochemistry; Indole Alkaloids; Dopaminergics; Neurotransmitters; Others; Asymmetric Synthesis; Chiral Building Blocks; Complex Molecules; Aromatics; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 200-047-9. This chemical's molecular formula is C33H40N2O9 and molecular weight is 608.68. What's more, both its IUPAC name and systematic name are the same which is called Methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate. Reserpine is an indole alkaloid antipsychotic and antihypertensive drug that has been used for the control of high blood pressure and for the relief of psychotic symptoms.
Physical properties about Reserpine are: (1)ACD/LogP: 4.447; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 2.71; (4)ACD/LogD (pH 7.4): 4.22; (5)ACD/BCF (pH 5.5): 25.79; (6)ACD/BCF (pH 7.4): 827.34; (7)ACD/KOC (pH 5.5): 114.26; (8)ACD/KOC (pH 7.4): 3665.46; (9)#H bond acceptors: 11; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 117.78 Å2; (13)Index of Refraction: 1.62; (14)Molar Refractivity: 160.936 cm3; (15)Molar Volume: 458.165 cm3; (16)Polarizability: 63.8×10-24cm3; (17)Surface Tension: 59.87 dyne/cm; (18)Density: 1.329 g/cm3; (19)Flash Point: 377.182 °C; (20)Enthalpy of Vaporization: 102.482 kJ/mol; (21)Boiling Point: 700.058 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.
Uses of Reserpine: it is used to produce other chemicals. For example, it can produce 2,11-dimethoxy-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester. This reaction needs reagent NaBH3CN and solvent trifluoroacetic acid at ambient temperature. The reaction time is 1 hour. The yield is 55 %.
When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and may cause inflammation to the skin or other mucous membranes. It is flammable and it is harmful if swallowed. In addition, it is irritating to eyes and the vapours may cause drowsiness and dizziness. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OC)[C@H]6[C@H]4C[C@@H]3c2nc1cc(OC)ccc1c2CCN3C[C@H]4C[C@@H](OC(=O)c5cc(OC)c(OC)c(OC)c5)[C@@H]6OC
(2) InChI: InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
(3) InChIKey: QEVHRUUCFGRFIF-MDEJGZGSSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 100mg/kg (100mg/kg) | Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972. | |
dog | LD50 | intravenous | 500ug/kg (.5mg/kg) | "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 234, 1973. | |
guinea pig | LD50 | subcutaneous | 65mg/kg (65mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 375, 1962. | |
guinea pig | LDLo | intravenous | 16mg/kg (16mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 600, 1973. | |
mouse | LD50 | intraperitoneal | 5mg/kg (5mg/kg) | European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 10, Pg. 519, 1975. | |
mouse | LD50 | intravenous | 21mg/kg (21mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Arzneimittel-Forschung. Drug Research. Vol. 14, Pg. 1040, 1964. |
mouse | LD50 | oral | > 50mg/kg (50mg/kg) | Drugs in Japan Vol. -, Pg. 1453, 1995. | |
mouse | LD50 | subcutaneous | 5610ug/kg (5.61mg/kg) | Drugs in Japan Vol. -, Pg. 1453, 1995. | |
rabbit | LD50 | intraperitoneal | 7mg/kg (7mg/kg) | Journal of Drug Research. Vol. 6(3), Pg. 19, 1974. | |
rabbit | LD50 | intravenous | 15mg/kg (15mg/kg) | "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 111, 1972. | |
rat | LD50 | intraperitoneal | 44mg/kg (44mg/kg) | BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 110, Pg. 20, 1957. |
rat | LD50 | intravenous | 15mg/kg (15mg/kg) | "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 111, 1972. | |
rat | LD50 | oral | 420mg/kg (420mg/kg) | BEHAVIORAL: ANTIPSYCHOTIC | Pesticide Science. Vol. 11, Pg. 555, 1980. |
rat | LD50 | subcutaneous | 25mg/kg (25mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 56, Pg. 377, 1960. |