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131-01-1

131-01-1 structure
131-01-1 structure
  • Name: Deserpidine
  • Chemical Name: deserpidine
  • CAS Number: 131-01-1
  • Molecular Formula: C32H38N2O8
  • Molecular Weight: 578.653
  • Catalog: API Circulatory system medication Antihypertensive drug
  • Create Date: 2018-08-05 15:59:25
  • Modify Date: 2025-08-25 10:41:42
  • 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].
Name deserpidine
Synonyms 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
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
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.
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

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)
RIDADR UN 9111
WGK Germany 3
4521-61-3 structure

4521-61-3

54290-61-8 structure

54290-61-8

~90%

131-01-1 structure

131-01-1

Literature: INDENA S.P.A. Patent: WO2005/95394 A1, 2005 ; Location in patent: Page/Page column 10-11 ;
4521-61-3 structure

4521-61-3

~%

131-01-1 structure

131-01-1

Literature: Journal of the American Chemical Society, , vol. 77, p. 4084,4086 Journal of the American Chemical Society, , vol. 77, p. 4335,4340
61-54-1 structure

61-54-1

~%

131-01-1 structure

131-01-1

Literature: Bulletin de la Societe Chimique de France, , p. 673,676 Annales Pharmaceutiques Francaises, , vol. 17, p. 15,21
Precursor  2

DownStream  0

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