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,...

General Information

Structure

Molecular Formula

C₃₃H₄₀N₂O₉

Molecular Mass

608.6787

Exact Mass

608.27338087

Charge

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

Calculated Properties

Provided by Enamine

CLogP

3.86

H Donor

Polar Surface Area

117.78

Rotatable Bonds

JChem

Polar Surface Area

117.78

H Donor

H Acceptors

Rotatable Bonds

Lipinski's Rule of Five

false

Log P

3.53

LogD (pH = 5.5)

2.01

LogD (pH = 7.4)

3.38

Acid pKa

16.29

Molar Refractivity

161.42

Polarizability

64.30

LOG S

-4.32

Data Source

Names and Identifiers

Brand Name

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 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 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

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

Synonyms

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 Name

Reserpine

Names and Identifiers

Registration numbers

PubChem CID

5770

PubChem SID

160963554465058632488811824278208

MDL Number

MFCD00005091

Beilstein Number

102014

CAS Number

50-55-5

Unique Ingredient Identifier

Chemspider ID

Medline Plus

CHEMBL

Wikipedia Title

KEGG ID

CHEBI ID

ATC CODE

DrugBank ID

EC Number

Registration numbers

Properties

Safety Information

-20°C

-20°C Freezer

Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

Free Base

corresponds for mass spectrometry

5 mg/L in water: isopropyl alcohol (1:1)

analytical standard

(limited shelf life, expiry date on the label)

Pharmacology Properties

gut/liver

Rx-only (some countries banned/discontinued)

50%

Reserpine

D (fetotoxic)

phase 1 = 4.5h,
phase 2 = 271h,
average = 33h

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity