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Substance Name: Reserpine [USP:INN:BAN:JAN]
RN: 50-55-5
UNII: 8B1QWR724A
InChIKey: QEVHRUUCFGRFIF-MDEJGZGSSA-N
Note
- An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.
Molecular Formula
- C33-H40-N2-O9
Molecular Weight
- 608.684
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Adrenergic Agents
- Adrenergic Uptake Inhibitors
- Antihypertensive
- Antihypertensive Agents
- Antipsychotic Agents
- Cardiovascular Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Drug / Therapeutic Agent
- Human Data
- Membrane Transport Modulators
- Mutation Data
- Natural Product
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Psychotropic Drugs
- Reproductive Effect
- Tranquilizing Agents
- TSCA Flag S (Substance is Identified in a Final Significant New Use Rule)
- Tumor Data
Superlist Classification Codes
- Overall Carcinogenic Evaluation: Group 3
- Reasonably Anticipated to be a Carcinogen
- Reportable Quantity (RQ) = 5000 lb
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Names and Synonyms
Name of Substance
- Reserpine
- Reserpine [USP:INN:BAN:JAN]
MeSH Heading
- Reserpine
Synonyms
- (-)-Reserpine
- 11,17-Dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)yohimban-16-carboxylic acid methyl ester
- 3,4,5-Trimethoxybenzoyl methyl reserpate
- 3P Reserp
- 4-25-00-01319 (Beilstein Handbook Reference)
- AI3-50146
- Alkarau
- Alserin
- Anquil
- Apoplon
- Apsical
- Ascoserpina
- Austrapine
- Banasil
- Benazyl
- Bioserpine
- BRN 0102014
- Carditivo
- Carpacil
- Carrserp
- Caswell No. 722A
- CCRIS 550
- Chloroserp-250
- Chloroserp-500
- Chloroserpin-250
- Chloroserpine-500
- Crystoserpine
- Demi-Regroton
- Deserpine
- Diupres 250
- Diupres 500
- Diurese-R
- Diutensen-R
- EINECS 200-047-9
- Elserpine
- Enipresser
- ENT 50146
- EPA Pesticide Chemical Code 123101
- Escaspere
- Eserpine
- Eskaserp
- Eskaserpine
- Gilucard
- H 520
- Helfoserpin
- Hiposerpil
- Hiserpia
- HSDB 213
- Hydro-Fluserpine #1
- Hydro-Reserpine-25
- Hydro-Reserpine-50
- Hydromox-R
- Hydropine
- Hydropres 25
- Hydropres 50
- Hydroserp
- Hydroserpalan
- Hydroserpine #1
- Hydroserpine Plus
- Hydrosine 25
- Hypersil
- Hypersine
- Idsoserp
- Interpina
- Key-serpine
- Kitine
- Klimanosid
- l-Carpserp
- Lemiserp
- Loweserp
- Mallopress
- Maviserpin
- Mayserpine
- Mephaserpin
- Metatensin #2
- Metatensin #4
- Methyl 18beta-hydroxy-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylate 3,4,5-trimethoxybenzoate (ester)
- Methyl reserpate 3,4,5-trimethoxybenzoic acid ester
- NCI-C50157
- Neo-antitensol
- Neoserfin
- Neoserp
- NSC 237659
- Purserpine
- Quiescin
- Rau-Sed
- Raucap
- Raudiford
- Raudixoid
- Raugal
- Raulen
- Rauloydin
- Raumorine
- Raunervil
- Raunorine
- Raupasil
- Raupoid
- Raurine
- Rausan
- Rausedan
- Rausedil
- Rausedyl
- Rauserpin-Alk
- Rauserpine
- Rauserpol
- Rausingle
- Rautrin
- Rauvlid
- Rauwasedin
- Rauwilid
- Rauwipur
- Rauwita
- Rauwoleaf
- Rawilid
- RCRA waste number U200
- Recipin
- Regroton
- Renese-R
- Resaltex
- Rese-Lar
- Resedrex
- Resedril
- Reser-AR
- Reserbal
- Resercaps
- Resercen
- Reserfia
- Reserjen
- Reserlor
- Reserp
- Reserpal
- Reserpamed
- Reserpanca
- Reserpene
- Reserpex
- Reserpic acid methyl ester 3,4,5-trimethoxybenzoate (ester)
- Reserpidefe
- Reserpil
- Reserpina
- Reserpina [INN-Spanish]
- Reserpine
- Reserpoid
- Resine
- Respital
- Restran
- Riserpa
- Rivasin
- Roxinoid
- Sandril
- Serpalan
- Serpanray
- Serpasil
- Serpate
- Serpivite
- UNII-8B1QWR724A
- V-Serp
- Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
Systematic Names
- 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-11,17-alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester)
- 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy- methyl ester 3,4,5-trimethoxybenzoate (ester) (8CI)
- Reserpine
- Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
Superlist Names
- RCRA waste no. U200
- Reserpine
- Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
Mixture Names
- Demi-Regroton
- Diupres
- Diutensen-R
- Hydropres
- Metatensin
- Naquival
- Regroton
- Renese R
- Salutensin
- Ser-Ap-Es
- Unipres
Registry Numbers
CAS Registry Number
- 50-55-5
FDA UNII
- 8B1QWR724A
Other Registry Numbers
- 1407-38-1
- 141099-49-2
- 8048-25-7
- 873409-80-4
- 909883-12-1
- 911481-85-1
System Generated Number
- 0000050555
Structure Descriptors
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/s1InChIKey
QEVHRUUCFGRFIF-MDEJGZGSSA-NSmiles
CO[C@H]1[C@@H](C[C@@H]2CN3CCc4c([nH]c5cc(OC)Toxicity
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 (0.5mg/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. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 264.5 | deg C | EXP | |
pKa Dissociation Constant | 6.6 | (none) | EXP | |
log P (octanol-water) | 3.320 | (none) | EST | |
Water Solubility | 73 | mg/L | 30 | EXP |
Vapor Pressure | 4.51E-16 | mm Hg | 25 | EST |
Henry's Law Constant | 5.36E-23 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 3.75E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.