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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
 

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

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)
  • 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/s1

InChIKey

QEVHRUUCFGRFIF-MDEJGZGSSA-N

Smiles

CO[C@H]1[C@@H](C[C@@H]2CN3CCc4c([nH]c5cc(OC)ccc45)[C@H]3C[C@@H]2[C@@H]1C(=O)OC)OC(=O)c6cc(OC)c(OC)c(OC)c6

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.