CAS 131-01-1|Deserpidine

Introduction：Basic information about CAS 131-01-1|Deserpidine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Deserpidine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Synonyms

Common Name	Deserpidine
CAS Number	131-01-1	Molecular Weight	578.653
Density	1.3±0.1 g/cm3	Boiling Point	676.1±55.0 °C at 760 mmHg
Molecular Formula	C₃₂H₃₈N₂O₈	Melting Point	~275 °C (dec.)(lit.)
MSDS	/	Flash Point	362.7±31.5 °C

Names

Name	deserpidine
Synonym	More Synonyms

Deserpidine BiologicalActivity

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 DiseaseResearch 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
InChIKey	CVBMAZKKCSYWQR-WCGOZPBSSA-N
SMILES	COC(=O)C1C2CC3c4[nH]c5ccccc5c4CCN3CC2CC(OC(=O)c2cc(OC)c(OC)c(OC)c2)C1OC
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

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

Recommended......