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50-55-5 molecular structure
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methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

ChemBase ID: 91
Molecular Formular: C33H40N2O9
Molecular Mass: 608.6787
Monoisotopic Mass: 608.27338087
SMILES and 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

Cite this record

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

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
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
IUPAC Traditional name
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
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
Brand Name
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
Synonyms
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
Reserpine Standard for LC-MS
Reserpine
(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
Sermix
Reserpoid
Sandril
Carpacil
Triserpin
利血平
LC-MS 利血平标准溶液
利血平
CAS Number
50-55-5
EC Number
200-047-9
MDL Number
MFCD00005091
Beilstein Number
102014
PubChem SID
24888118
46505863
160963554
24278208
PubChem CID
5770
CHEBI ID
28487
ATC CODE
C02AA02
CHEMBL
772
Chemspider ID
5566
DrugBank ID
DB00206
KEGG ID
D00197
Unique Ingredient Identifier
8B1QWR724A
Wikipedia Title
Reserpine
Medline Plus
a601107

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 16.290113  H Acceptors
H Donor LogD (pH = 5.5) 1.7332709 
LogD (pH = 7.4) 3.2777264  Log P 3.531496 
Molar Refractivity 161.4185 cm3 Polarizability 64.298744 Å3
Polar Surface Area 117.78 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five false 
Log P 4.05  LOG S -4.73 
Solubility (Water) 1.13e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
73 mg/L expand Show data source
Chloroform expand Show data source
Methanol (hot) expand Show data source
Apperance
Off-White to Pale Yellow Solid expand Show data source
Melting Point
~265 °C (dec.) expand Show data source
>220°C (dec.) expand Show data source
Flash Point
22 °C expand Show data source
71.6 °F expand Show data source
Optical Rotation
[α]20/D -123±3°, c = 1% in chloroform expand Show data source
Hydrophobicity(logP)
3.2 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Storage Warning
Hygroscopic expand Show data source
RTECS
ZG0350000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
1219 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
3 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
10-36-67 expand Show data source
22 expand Show data source
Safety Statements
22-36/37/39 expand Show data source
26 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Danger expand Show data source
Warning expand Show data source
GHS Hazard statements
H225-H319-H336 expand Show data source
H302 expand Show data source
GHS Precautionary statements
P210-P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 1219 3/PG 2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
oral expand Show data source
Bioavailability
50% expand Show data source
Excretion
62% feces / 8% urine expand Show data source
Half Life
phase 1 = 4.5h,
phase 2 = 271h,
average = 33h
expand Show data source
Metabolism
gut/liver expand Show data source
Legal Status
Rx-only (some countries banned/discontinued) expand Show data source
Pregnancy Category
D (fetotoxic) expand Show data source
US Licence
Reserpine expand Show data source
Gene Information
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 Show data source
Mechanism of Action
Disruption of norepinephrine, serotonin, and dopamine presynaptic vesicles by the transporter VMAT expand Show data source
Purity
≥99.0% (HPLC) expand Show data source
Concentration
5 mg/L in water: isopropyl alcohol (1:1) expand Show data source
Grade
analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
corresponds for mass spectrometry expand Show data source
Biological Source
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 Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Application(s)
Antiadrenergic expand Show data source
Anticonvulsant agent expand Show data source
Antihypertensive agent acting by depleting stores of noradrenaline in sympathetic neurones expand Show data source
Antineoplastic agent expand Show data source
Possesses sedative tranquilliser props. expand Show data source
Quality
crystallized expand Show data source
Empirical Formula (Hill Notation)
C33H40N2O9 expand Show data source

DETAILS

DETAILS

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 - 43530 external link
Biochem/physiol Actions
Inhibits vesicular uptake of catecholamines and serotonin.
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.
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.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
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  • • 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)
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  • • 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)
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  • • Pearlman, B.A., J.A.C.S., 1979, 101, 6404, (synth)
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  • • 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)
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  • • 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)
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  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 343; 386
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  • • 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
  • • : 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
  • • http://en.wikipedia.org/wiki/Reserpine
  • • Moser M: "Cost containment" in the management of hypertension. Ann Intern Med. 1987 Jul;107(1):107-9. Pubmed
  • • 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)
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