Deserpidine

Names

[ CAS No. ]:
131-01-1

[ Name ]:
Deserpidine

[Synonym ]:
methyl (3β,16β,17α,18β,20α)-17-methoxy-18-{[(3,4,5-trimethoxyphenyl)carbonyl]oxy}yohimban-16-carboxylate
DESERPIDINE
canescine
(3b,16b,17a,18b,20a)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-3,20-yohimban-16-carboxylic Acid Methyl Ester
MFCD00078228
Harmonyl
Recanescin
Canescin
Deserpidin
Methyl-(1S,2R,3R,4aS,13bR,14aS)-2-methoxy-3-{[(3,4,5-trimethoxyphenyl)carbonyl]oxy}-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isochinolin-1-carboxylat
(1S,2R,3R,4aS,13bR,14aS)-2-méthoxy-3-{[(3,4,5-triméthoxyphényl)carbonyl]oxy}-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodécahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoléine-1-carboxylate de méthyle
Yohimban-16-carboxylic acid, 17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3b,16b,17a,18b,20a)-
Desepridine
11-desmethoxyreserpine
17a-Methoxy-18b-[(3,4,5-trimethoxybenzoyl)oxy]-3b,20a-yohimban-16b-carboxylic Acid Methyl Ester
17-methoxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimbane-16-carboxylic acid methyl ester
Raunormin
Methyl (3β,16β,17α,18β,20α)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
17α-Methoxy-18β-[(3,4,5-trimethoxybenzoyl)oxy]-3β,20α-yohimban-16β-carboxylic acid methyl ester
Yohimban-16-carboxylic acid, 17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3β,16β,17α,18β,20α)-
methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
EINECS 205-004-8
recanescine
Raunormine
Deserpidic Acid Methyl Ester 3,4,5-Trimethoxybenzoate
methyl (1S,2R,3R,4aS,13bR,14aS)-2-methoxy-3-{[(3,4,5-trimethoxyphenyl)carbonyl]oxy}-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate

Biological Activity

[Description]:

Deserpidine (Harmonyl) is an alkaloid isolated from the root of Rauwolfia canescens related to Reserpine. Deserpidine is used as an antihypertensive agent and a tranquilizer. Deserpidine is a competitive angiotensin converting enzyme (ACE) inhibitor. Deserpidine also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex[1][2][3].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Angiotensin-converting Enzyme (ACE)

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

[Target]

Angiotensin converting enzyme (ACE)[3]

[In Vitro]

Deserpidine is an effective ganglionic blocking agent, which differs from Reserpine only by the absence of a methoxy group at C-11. Deserpidine has been used in the treatment of hypertension and psychosis. In addition, Deserpidine appears to act as a controller of other cardiac disorders[1][2].

[References]

[1]. Varchi G, et al. Synthesis of deserpidine from reserpine. J Nat Prod. 2005 Nov;68(11):1629-31.

[2]. Zhang H, et al. Liquid chromatography/tandem mass spectrometry method for the quantification of deserpidine in human plasma: Application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Oct 1;877(27):3221-5.

[3]. Fulton SC, et al. Comparison of the effectiveness of deserpidine, reserpine, and alpha-methyltyrosine on brain biogenic amines. Fed Proc. 1976 Dec;35(14):2558-62.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
676.1±55.0 °C at 760 mmHg

[ Melting Point ]:
~275 °C (dec.)(lit.)

[ Molecular Formula ]:
C₃₂H₃₈N₂O₈

[ Molecular Weight ]:
578.653

[ Flash Point ]:
362.7±31.5 °C

[ Exact Mass ]:
578.262817

[ PSA ]:
108.55000

[ LogP ]:
4.19

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.626

[ Storage condition ]:
-20°C

[ Water Solubility ]:
slightly soluble

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: ZG0875000

CHEMICAL NAME :: 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-17-alpha-methoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester)

CAS REGISTRY NUMBER :: 131-01-1

BEILSTEIN REFERENCE NO. :: 0101820

LAST UPDATED :: 199612

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C32-H38-N2-O8

MOLECULAR WEIGHT :: 578.72

WISWESSER LINE NOTATION :: T F6 D5 C666 EM ON&&TTTJ SOVR CO1 DO1 EO1& TO1 UVO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,104,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Behavioral - coma Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 44,688,1955

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Behavioral - coma Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 44,688,1955 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 25690 mg/kg/4W-C

TOXIC EFFECTS :: Related to Chronic Data - death

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 44,688,1955

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 80 mg/kg/4D-I

TOXIC EFFECTS :: Related to Chronic Data - death

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 44,688,1955 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 16 mg/kg/9Y-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 2,672,1974

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 54 mg/kg/77W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors Blood - lymphoma, including Hodgkin's disease

REFERENCE :: COREAF Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. (Paris, France) V.1-261, 1835-1965. For publisher information, see CRASEV. Volume(issue)/page/year: 254,1535,1962 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 4950 mg/kg

SEX/DURATION :: female 6-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 155,2291,1961

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 1600 ug/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 83,1405,1962 *** REVIEWS *** TOXICOLOGY REVIEW CLPTAT Clinical Pharmacology and Therapeutics (St. Louis). (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1960- Volume(issue)/page/year: 5,480,1964 TOXICOLOGY REVIEW ADVPA3 Advances in Pharmacology. (New York, NY) V.1-6, 1962-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 4,263,1966 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X9135 No. of Facilities: 35 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 430 (estimated) No. of Female Employees: 239 (estimated)

Safety Information

[ RIDADR ]:
UN 9111

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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