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50-55-5 分子结构
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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和InChIs

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

引用这个纪录

CBID:91 http://www.chembase.cn/molecule-91.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]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[11.8.0.0^{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[11.8.0.02,10.04,9.015,20]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[11.8.0.0^{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
CAS号
50-55-5
EC号
200-047-9
MDL号
MFCD00005091
Beilstein号
102014
PubChem SID
160963554
24888118
24278208
46505863
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

理论计算性质

JChem ALOGPS 2.1
Acid pKa 16.290113  质子受体
质子供体 LogD (pH = 5.5) 1.7332709 
LogD (pH = 7.4) 3.2777264  Log P 3.531496 
摩尔折射率 161.4185 cm3 极化性 64.298744 Å3
极化表面积 117.78 Å2 可自由旋转的化学键 10 
里宾斯基五规则 false 
Log P 4.05  LOG S -4.73 
溶解度 1.13e-02 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
73 mg/L expand 查看数据来源
Chloroform expand 查看数据来源
Methanol (hot) expand 查看数据来源
外观
Off-White to Pale Yellow Solid expand 查看数据来源
熔点
~265 °C (dec.) expand 查看数据来源
>220°C (dec.) expand 查看数据来源
闪点
22 °C expand 查看数据来源
71.6 °F expand 查看数据来源
比旋光度
[α]20/D -123±3°, c = 1% in chloroform expand 查看数据来源
疏水性(logP)
3.2 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer expand 查看数据来源
保存注意事项
Hygroscopic expand 查看数据来源
RTECS编号
ZG0350000 expand 查看数据来源
欧盟危险性物质标志
刺激性(Irritant) 刺激性(Irritant) (Xi) expand 查看数据来源
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
联合国危险货物编号
1219 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
1 expand 查看数据来源
3 expand 查看数据来源
联合国危险货物等级
3 expand 查看数据来源
联合国危险货物包装类别(PG)
2 expand 查看数据来源
危险公开号
10-36-67 expand 查看数据来源
22 expand 查看数据来源
安全公开号
22-36/37/39 expand 查看数据来源
26 expand 查看数据来源
GHS危险品标识
GHS02 expand 查看数据来源
GHS07 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
Warning expand 查看数据来源
GHS危险声明
H225-H319-H336 expand 查看数据来源
H302 expand 查看数据来源
GHS警示性声明
P210-P261-P305 + P351 + P338 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand 查看数据来源
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand 查看数据来源
RID/ADR
UN 1219 3/PG 2 expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
给药途径
oral expand 查看数据来源
生物利用度
50% expand 查看数据来源
排泄
62% feces / 8% urine expand 查看数据来源
半衰期
phase 1 = 4.5h,
phase 2 = 271h,
average = 33h
expand 查看数据来源
代谢
gut/liver expand 查看数据来源
法定药品分级
Rx-only (some countries banned/discontinued) expand 查看数据来源
妊娠期药物分类
D (fetotoxic) expand 查看数据来源
美国(FDA)药品许可证
Reserpine expand 查看数据来源
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) expand 查看数据来源
生物活性机理
Disruption of norepinephrine, serotonin, and dopamine presynaptic vesicles by the transporter VMAT expand 查看数据来源
纯度
≥99.0% (HPLC) expand 查看数据来源
浓度
5 mg/L in water: isopropyl alcohol (1:1) expand 查看数据来源
级别
analytical standard expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
适用性
corresponds for mass spectrometry expand 查看数据来源
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 expand 查看数据来源
有效期
(limited shelf life, expiry date on the label) expand 查看数据来源
应用领域
Antiadrenergic expand 查看数据来源
Anticonvulsant agent expand 查看数据来源
Antihypertensive agent acting by depleting stores of noradrenaline in sympathetic neurones expand 查看数据来源
Antineoplastic agent expand 查看数据来源
Possesses sedative tranquilliser props. expand 查看数据来源
品质说明
crystallized expand 查看数据来源
Empirical Formula (Hill Notation)
C33H40N2O9 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB00206 external link
Item Information
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 external link
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 external link
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 external link
Biochem/physiol Actions
Inhibits vesicular uptake of catecholamines and serotonin.
Sigma Aldrich -  43530 external link
Biochem/physiol Actions
Inhibits vesicular uptake of catecholamines and serotonin.
Toronto Research Chemicals -  R144600 external link
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

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • : 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
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