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

• ChemBase编号: 91
• 分子式: C33H40N2O9
• 平均质量: 608.6787
• 单一同位素质量: 608.27338087
• 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
• Canonical 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
• 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

名称和登记号

名称

• 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,^1^0.0^4,^9.0^1^5,^2^0]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[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]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,^1^0.0^4,^9.0^1^5,^2^0]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[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
• 商标名: Cam-Ap-Es; Demi-Regroton; Diupres-250; Diupres-500; Diutensen-R; Dralserp; Hiserpia; Hydrap-ES; Hydromox R; Hydroserpine Plus (R-H-H); Metatensin #2; Metatensin #4; Naquival; Novoreserpine; Rau-Sed; Regroton; Renese-R; Reserfia; Salutensin; Salutensin-Demi; Sandril; Ser-A-Gen; Serpalan; Serpanray; Serpasil; Serpasil-Apresoline; Serpasil-Esidrix #1; Serpasil-Esidrix #2; Serpate; Serpivite; Unipres
• 别名: 利血平; 利血平; LC-MS 利血平标准溶液; Reserpine; (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-carboxylate; (3β,16β,17α,18β,20α)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic Acid Methyl Ester; 3,4,5-Trimethoxybenzoyl Methyl Reserpate; Anquil; Apoplon; Rivasin; Serpasil; Temposerpine; Triserpin; Sermix; Reserpoid; Sandril; Carpacil; Reserpine; Reserpine Standard for LC-MS

登记号

• CAS号: 50-55-5
• EC号: 200-047-9
• MDL号: MFCD00005091
• Beilstein号: 102014
• PubChem SID: 160963554; 46505863; 24278208; 24888118
• PubChem CID: 5770
• CHEBI ID: 28487
• ATC码: C02AA02
• CHEMBL: 772
• Chemspider ID: 5566
• DrugBank ID: DB00206
• KEGG ID: D00197
• 美国药典/FDA物质标识码: 8B1QWR724A
• 维基百科标题: Reserpine
• Medline Plus: a601107

理论计算性质

JChem

• Acid pKa: 16.290113
• 质子受体: 8
• 质子供体: 1
• LogD (pH = 5.5): 1.7332709
• LogD (pH = 7.4): 3.2777264
• Log P: 3.531496
• 摩尔折射率: 161.4185 cm^3
• 极化性: 64.298744 Å^3
• 极化表面积: 117.78 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.05
• LOG S: -4.73
• 溶解度: 1.13e-02 g/l

分子性质

理化性质

• 溶解度: 73 mg/L; Chloroform; Methanol (hot)
• 外观: Off-White to Pale Yellow Solid
• 熔点: ~265 °C (dec.); >220°C (dec.)
• 闪点: 22 °C; 71.6 °F
• 比旋光度: [α]20/D -123±3°, c = 1% in chloroform
• 疏水性(logP): 3.2

安全信息

• 保存条件: -20°C; -20°C Freezer
• 保存注意事项: Hygroscopic
• RTECS编号: ZG0350000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1219
• 德国WGK号: 1; 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 10-36-67; 22
• 安全公开号: 22-36/37/39; 26
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Danger; Warning
• GHS危险声明: H225-H319-H336; H302
• GHS警示性声明: P210-P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1219 3/PG 2
• 保存温度: 2-8°C

药理学性质

• 给药途径: oral
• 生物利用度: 50%
• 排泄: 62% feces / 8% urine
• 半衰期: phase 1 = 4.5h,; phase 2 = 271h, ; average = 33h
• 代谢: gut/liver
• 法定药品分级: Rx-only (some countries banned/discontinued)
• 妊娠期药物分类: D (fetotoxic)
• 美国（FDA）药品许可证: Reserpine
• 相关基因信息: human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242), HTR4(3360), HTR5A(3361), HTR5B(645694), HTR6(3362), HTR7(3363)
• 生物活性机理: Disruption of norepinephrine, serotonin, and dopamine presynaptic vesicles by the transporter VMAT

产品相关信息

• 纯度: ≥99.0% (HPLC)
• 浓度: 5 mg/L in water: isopropyl alcohol (1:1)
• 级别: analytical standard
• 成盐信息: Free Base
• 适用性: corresponds for mass spectrometry
• 生物来源: Alkaloid from Rauwolfia serpentina, Rauwolfia vomitoria, Rauwolfia macrophylla , very many other Rauwolfia spp., Vinca minor, Alstonia constricta and many other spp. in the Apocynaceae, e.g. Tenduzia longifolia, Vallesia dichotoma and Excavatia coccinea
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Antiadrenergic; Anticonvulsant agent; Antihypertensive agent acting by depleting stores of noradrenaline in sympathetic neurones; Antineoplastic agent; Possesses sedative tranquilliser props.
• 品质说明: crystallized
• Empirical Formula (Hill Notation): C33H40N2O9

详细说明

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]

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.

Sigma Aldrich - 83580

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

Sigma Aldrich - 43530

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

Toronto Research Chemicals - 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.

参考文献

• : 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
• http://en.wikipedia.org/wiki/Reserpine
• Muller, J.M., et al.: Experientia, 8, 338 (1952)
• Schirmer, R.E., et al.: Anal. Profiles Drug Subs., 4, 384 (1952)
• Diener, R.M., et al.: Toxicol. Pathol., 8, 1 (1952)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1069C, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 615A, (nmr)
• Furlenmeyer, A. et al., Experientia, 1953, 9, 331, (uv, ir)
• Velluz, L. et al., Bull. Soc. Chim. Fr., 1958, 145; 673, (synth)
• Woodward, R.B. et al., Tetrahedron, 1958, 2, 1, (synth)
• Ban, Y. et al., Tetrahedron, 1964, 20, 2877, (config)
• Schlittler, E., Alkaloids (N.Y.), 1965, 8, 287, (rev)
• Levin, R.H. et al., J.O.C., 1973, 38, 1983, (cmr)
• Taylor, W.I. et al., The Vinca Alkaloids, Marcel Dekker, 1973, (rev, props)
• Becker, O. et al., Org. Mass Spectrom., 1977, 12, 461, (ms)
• Pearlman, B.A., J.A.C.S., 1979, 101, 6404, (synth)
• Bein, H.J., Handb. Exp. Pharmacol., (Part 1), 1980, 55, 43-58, (rev, pharmacol)
• IARC Monog., 1980, 24, 211; Suppl., 6, 485; Suppl., 7, 330, (rev, tox)
• Wender, P.A. et al., J.A.C.S., 1980, 102, 6157, (synth)
• 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)
• Szntay, C. et al., Alkaloids (N.Y.), 1986, 27, 253, (pharmacol, bibl)
• Martin, S.F. et al., J.A.C.S., 1987, 109, 6124, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7993, (synonyms)
• Stork, G., Pure Appl. Chem., 1989, 61, 439, (synth)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 343; 386
• Chu, C.S. et al., Chem. Comm., 1996, 1537, (synth)
• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 55, (bibl, synth)
• Hanessian, S. et al., J.O.C., 1997, 62, 465, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DIG800; DIH000; RDK000