Reserpine(50-55-5) was isolated in 1952 from the dried root of Rauwolfia serpentina,it has been discontinued in the UK for some years due to its numerous interactions and side effects,it was also highly influential in promoting the thought of a biogenic-amine hypothesis of depression.

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 330.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 10 ,1976,p. 217.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 ,1980,p. 211.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 ,1980,p. 211.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-193 ,1980. . Reported in EPA TSCA Inventory.

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.