CAS 50-55-5|Naquival|Hydroserpine Plus (R-H-H)|methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,...

基本信息

化学结构

分子式

C₃₃H₄₀N₂O₉

分子量

608.6787

精确质量

608.27338087

电荷

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

Canonic Smiles

COc1ccc2c(c1)[nH]c1c2CCN2[C@@H]1C[C@H]1[C@@H](C2)C[C@H]([C@@H]([C@H]1C(=O)OC)OC)OC(=O)c1cc(OC)c(c(c1)OC)OC

Isomeric Smiles

O([C@@H]1[C@H]([C@@H]2[C@@H](CN3[C@H](C2)c2[nH]c4c(c2CC3)ccc(OC)c4)C[C@H]1OC(=O)c1cc(OC)c(OC)c(OC)c1)C(=O)OC)C

计算属性

Enamine提供

CLogP

3.86

质子供体

极化表面积

117.78

可自由旋转的化学键

JChem

极化表面积

117.78

质子供体

质子受体

可自由旋转的化学键

里宾斯基五规则

false

Log P

3.53

LogD (pH = 5.5)

2.01

LogD (pH = 7.4)

3.38

Acid pKa

16.29

摩尔折射率

161.42

极化性

64.30

LOG S

-4.32

数据来源

名称和标识

商标名

SerpiviteSerpateRenese-RUnipresMetatensin #4Hydroserpine Plus (R-H-H)HiserpiaMetatensin #2Rau-SedSerpasil-ApresolineDiupres-500NaquivalReserfiaHydrap-ESSalutensin-DemiDiutensen-RDralserpSerpanrayNovoreserpineSalutensinSerpasil-Esidrix #2SerpasilSerpasil-Esidrix #1SandrilCam-Ap-EsRegrotonSerpalanSer-A-GenDemi-RegrotonHydromox RDiupres-250

IUPAC标准名

methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

IUPAC传统名

unipres methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

别名

ReserpineReserpine利血平(1S,2R,3R,4aS,13bR,14aS)-methyl 2,11-dimethoxy-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylateReserpine Standard for LC-MSLC-MS 利血平标准溶液利血平Apoplon(3β,16β,17α,18β,20α)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic Acid Methyl EsterTemposerpineAnquilSerpasilRivasinTriserpin3,4,5-Trimethoxybenzoyl Methyl ReserpateSermixReserpoidCarpacilSandril

API名称

Reserpine

名称和标识

数据登录号

PubChem CID

5770

PubChem SID

160963554465058632427820824888118

Beilstein号

MDL号

CAS号

Chemspider ID

美国药典/FDA物质标识码

CHEMBL

Medline Plus

维基百科标题

KEGG ID

CHEBI ID

DrugBank ID

ATC码

EC号

数据登录号

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

DrugBank

DB00206

Drug Groups

approved

Description

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. [PubChem]

Indication

Foe the treatment of hypertension

Pharmacology

Reserpine is an adrenergic blocking agent used to treat mild to moderate hypertension via the disruption of norepinephrine vesicular storage. The antihypertensive actions of Reserpine are a result of its ability to deplete catecholamines from peripheral sympathetic nerve endings. These substances are normally involved in controlling heart rate, force of cardiac contraction and peripheral resistance.

Toxicity

Possible human carcinogen. May cause reproductive harm. ORL-RAT LD₅₀ 420 mg/kg; IPR-RAT LD₅₀ 44 mg/kg; IVN-RAT LD₅₀ 15 mg/kg; ORL-MUS LD₅₀ 200 mg/kg; SCU-MUS LD₅₀ 52 mg/kg; IPR-RBT LD₅₀ 7 mg/kg

Affected Organisms

Humans and other mammals

Protein Binding

62%

Elimination

Reserpine is extensively metabolized to inactive compounds. It is slowly excreted via the urine and feces.

References

• : Five-year findings of the hypertension detection and follow-up program. I. Reduction in mortality of persons with high blood pressure, including mild hypertension. Hypertension Detection and Follow-up Program Cooperative Group. JAMA. 1979 Dec 7;242(23):2562-71. [Pubmed]

• : Effects of treatment on morbidity in hypertension. Results in patients with diastolic blood pressures averaging 115 through 129 mm Hg. JAMA. 1967 Dec 11;202(11):1028-34. [Pubmed]

• : Prevention of stroke by antihypertensive drug treatment in older persons with isolated systolic hypertension. Final results of the Systolic Hypertension in the Elderly Program (SHEP). SHEP Cooperative Research Group. JAMA. 1991 Jun 26;265(24):3255-64. [Pubmed]

• Chobanian AV, Bakris GL, Black HR, Cushman WC, Green LA, Izzo JL Jr, Jones DW, Materson BJ, Oparil S, Wright JT Jr, Roccella EJ: The Seventh Report of the Joint National Committee on Prevention, Detection, Evaluation, and Treatment of High Blood Pressure: the JNC 7 report. JAMA. 2003 May 21;289(19):2560-72. Epub 2003 May 14. [Pubmed]

• Moser M: "Cost containment" in the management of hypertension. Ann Intern Med. 1987 Jul;107(1):107-9. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

Selleck Chemicals

S1601

Research Area: Cardiovascular Disease
Biological Activity:
Reserpine is an indole alkaloid antipsychotic and antihypertensive drug that has been used for the control of high blood pressure and for the relief of psychotic symptoms, although because of the development of better drugs for these purposes and because of its numerous side-effects, it is rarely used today. Reserpine acts by blocking the vesicular monoamine transporter VMAT, which normally transports free norepinephrine, serotonin, and dopamine from the cytoplasm of the presynaptic nerve into vesicles for subsequent release into the synaptic cleft. The unprotected neurotransmitters are then metabolized by MAO and therefore never reach the synapse. [1]

Wikipedia

Reserpine

Sigma Aldrich

R0875

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Inhibits vesicular uptake of catecholamines and serotonin.

43530

Biochem/physiol Actions
Inhibits vesicular uptake of catecholamines and serotonin.

83580

Biochem/physiol Actions
Inhibits vesicular uptake of catecholamines and serotonin.

TRC

R144600

An indole alkaloid found in Rauwolfia serpentina. Inhibits vesicular uptake of catecholamines and serotonin. Reserpine is reasonably anticipated to be a human carcinogen. Antihypertensive.

描述信息

参考文献

PubChem文献

数据源提供

• Moser M: "Cost containment" in the management of hypertension. Ann Intern Med. 1987 Jul;107(1):107-9. Pubmed

• : Effects of treatment on morbidity in hypertension. Results in patients with diastolic blood pressures averaging 115 through 129 mm Hg. JAMA. 1967 Dec 11;202(11):1028-34. Pubmed

• http://en.wikipedia.org/wiki/Reserpine

• Diener, R.M., et al.: Toxicol. Pathol., 8, 1 (1952)

• Muller, J.M., et al.: Experientia, 8, 338 (1952)

• Schirmer, R.E., et al.: Anal. Profiles Drug Subs., 4, 384 (1952)

• Furlenmeyer, A. et al., Experientia, 1953, 9, 331, (uv, ir)

• Bein, H.J., Handb. Exp. Pharmacol., (Part 1), 1980, 55, 43-58, (rev, pharmacol)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7993, (synonyms)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 343; 386

• Taylor, W.I. et al., The Vinca Alkaloids, Marcel Dekker, 1973, (rev, props)

• Becker, O. et al., Org. Mass Spectrom., 1977, 12, 461, (ms)

• Szntay, C. et al., Alkaloids (N.Y.), 1986, 27, 253, (pharmacol, bibl)

• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 55, (bibl, synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DIG800; DIH000; RDK000

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 615A, (nmr)

• Ban, Y. et al., Tetrahedron, 1964, 20, 2877, (config)

• Wender, P.A. et al., J.A.C.S., 1980, 102, 6157, (synth)

• Chu, C.S. et al., Chem. Comm., 1996, 1537, (synth)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1069C, (ir)

• Levin, R.H. et al., J.O.C., 1973, 38, 1983, (cmr)

• IARC Monog., 1980, 24, 211; Suppl., 6, 485; Suppl., 7, 330, (rev, tox)

• Muhtadi, F.J., Anal. Profiles Drug Subst., 1984, 13, 737, (rev, ir, pmr, cmr, ms, anal)

• Lounasmaa, M. et al., Heterocycles, 1985, 23, 371, (pmr)

• Martin, S.F. et al., J.A.C.S., 1987, 109, 6124, (synth)

• Hanessian, S. et al., J.O.C., 1997, 62, 465, (synth)

• Velluz, L. et al., Bull. Soc. Chim. Fr., 1958, 145; 673, (synth)

• Woodward, R.B. et al., Tetrahedron, 1958, 2, 1, (synth)

• Schlittler, E., Alkaloids (N.Y.), 1965, 8, 287, (rev)

• Pearlman, B.A., J.A.C.S., 1979, 101, 6404, (synth)

• Stork, G., Pure Appl. Chem., 1989, 61, 439, (synth)

参考文献

生物活性

PubChem BioAssay

生物活性