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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H40N2O9.C6H8O6
Molecular Weight 784.8028
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RESERPINE ASCORBATE

SMILES

OC[C@H](O)[C@H]1OC(=O)C(O)=C1O.CO[C@H]2[C@@H](C[C@@H]3CN4CCC5=C(NC6=C5C=CC(OC)=C6)[C@H]4C[C@@H]3[C@@H]2C(=O)OC)OC(=O)C7=CC(OC)=C(OC)C(OC)=C7

InChI

InChIKey=WNJQGGIUASELQW-YDTMYOOKSA-N
InChI=1S/C33H40N2O9.C6H8O6/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;7-1-2(8)5-3(9)4(10)6(11)12-5/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3;2,5,7-10H,1H2/t18-,22+,24-,27-,28+,31+;2-,5+/m10/s1

HIDE SMILES / InChI

Molecular Formula C6H8O6
Molecular Weight 176.1241
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C33H40N2O9
Molecular Weight 608.6787
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Reserpine is an alkaloid, isolated from the Rauwolfia serpentina plant and developed by Ciba pharma. Reserpine was approved by FDA for the treatment of hypertension and psychotic disorders. The drug exerts its effect by blocking two vesicular monoamine transporters, VMAT1 and VMAT2. The blockade results in vesicles that lose their ability to store neurotransmitter molecules. Neurotransmitters, thus retained in cytosol, are then neutralized by MAO.

Originator

Curator's Comment: Later Ciba-Geigy and now Novartis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
160.0 nM [IC50]
350.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RESERPINE

Approved Use

Mild essential hypertension; also useful as adjunctive therapy with other antihypertensive agents in the more severe forms of hypertension; relief of symptoms in agitated psychotic states (e.g., schizophrenia), primarily in those individuals unable to tolerate phenothiazine derivatives or in those who also require antihypertensive medication.

Launch Date

1955
Palliative
RESERPINE

Approved Use

Mild essential hypertension; also useful as adjunctive therapy with other antihypertensive agents in the more severe forms of hypertension; relief of symptoms in agitated psychotic states (e.g., schizophrenia), primarily in those individuals unable to tolerate phenothiazine derivatives or in those who also require antihypertensive medication.

Launch Date

1955
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.1 ng/mL
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RESERPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
200 h
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RESERPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
4.5 h
0.25 mg single, oral
dose: 0.25 mg
route of administration: Oral
experiment type: SINGLE
co-administered: POLYTHIAZIDE
RESERPINE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RESERPINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.25 mg 2 times / day multiple, oral
Dose: 0.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 0.25 mg, 2 times / day
Sources:
unhealthy, 41.2 years
Health Status: unhealthy
Age Group: 41.2 years
Sex: M+F
Sources:
Disc. AE: Upper abdominal pain, Postural hypotension...
AEs leading to
discontinuation/dose reduction:
Upper abdominal pain (1 patient)
Postural hypotension (1 patient)
Electrocardiogram abnormal (1 patient)
Sources:
0.25 mg 2 times / day multiple, oral
Dose: 0.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 0.25 mg, 2 times / day
Sources:
unhealthy, 41.2 years
Health Status: unhealthy
Age Group: 41.2 years
Sex: M+F
Sources:
Disc. AE: Drowsiness, Light headedness...
AEs leading to
discontinuation/dose reduction:
Drowsiness (1 patient)
Light headedness (light, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Electrocardiogram abnormal 1 patient
Disc. AE
0.25 mg 2 times / day multiple, oral
Dose: 0.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 0.25 mg, 2 times / day
Sources:
unhealthy, 41.2 years
Health Status: unhealthy
Age Group: 41.2 years
Sex: M+F
Sources:
Postural hypotension 1 patient
Disc. AE
0.25 mg 2 times / day multiple, oral
Dose: 0.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 0.25 mg, 2 times / day
Sources:
unhealthy, 41.2 years
Health Status: unhealthy
Age Group: 41.2 years
Sex: M+F
Sources:
Upper abdominal pain 1 patient
Disc. AE
0.25 mg 2 times / day multiple, oral
Dose: 0.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 0.25 mg, 2 times / day
Sources:
unhealthy, 41.2 years
Health Status: unhealthy
Age Group: 41.2 years
Sex: M+F
Sources:
Drowsiness 1 patient
Disc. AE
0.25 mg 2 times / day multiple, oral
Dose: 0.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 0.25 mg, 2 times / day
Sources:
unhealthy, 41.2 years
Health Status: unhealthy
Age Group: 41.2 years
Sex: M+F
Sources:
Light headedness light, 1 patient
Disc. AE
0.25 mg 2 times / day multiple, oral
Dose: 0.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 0.25 mg, 2 times / day
Sources:
unhealthy, 41.2 years
Health Status: unhealthy
Age Group: 41.2 years
Sex: M+F
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [Activation >3.9811 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no
no
unlikely [Inhibition 20 uM]
weak [IC50 133 uM]
weak [IC50 133 uM]
weak [IC50 58 uM]
yes [IC50 2.8 uM]
yes [IC50 20.4 uM]
yes [IC50 26.3 uM]
yes [IC50 <0.03 uM]
yes [IC50 <0.2 uM]
yes [Inhibition 20 uM]
yes [Inhibition 20 uM]
yes [Ki 1.38 uM]
yes [Ki 295 uM]
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Rat stomach ECL cells: mode of activation of histidine decarboxylase.
2003-06-15
Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition.
2003-06
The Seventh Report of the Joint National Committee on Prevention, Detection, Evaluation, and Treatment of High Blood Pressure: the JNC 7 report.
2003-05-21
Assessment of a controlled release hydrophilic matrix formulation for metoclopramide HCl.
2003-05
Osteology and skeletal development of Apalone spinifera (Reptilia: Testudines: Trionychidae).
2003-04
Studies on the long-term thermal stability of stationary phases in subcritical water chromatography.
2003-03-07
DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells.
2003-02-24
Analysis of flecainide and two metabolites in biological specimens by HPLC: application to a fatal intoxication.
2003-02-18
Antitumour 2-(4-aminophenyl)benzothiazoles generate DNA adducts in sensitive tumour cells in vitro and in vivo.
2003-02-10
Optimization and validation of conventional and micellar LC methods for the analysis of methyltestosterone in sugar-coated pills.
2003-02-05
Determination of peptides and amino acids from wool and beer with sensitive fluorescent reagent 2-(9-carbazole)-ethyl chloroformate by reverse phase high-performance liquid chromotography and liquid chromotography mass spectrometry.
2003-02-01
Expression of heart K+ channels in adrenalectomized and catecholamine-depleted reserpine-treated rats.
2003-02
Effects of CB1 cannabinoid receptor modulating compounds on the hyperkinesia induced by high-dose levodopa in the reserpine-treated rat model of Parkinson's disease.
2003-02
The physiology of overwintering in a turtle that occupies multiple habitats, the common snapping turtle (Chelydra serpentina).
2003-01-17
Growth-inhibitory effects of the chemopreventive agent indole-3-carbinol are increased in combination with the polyamine putrescine in the SW480 colon tumour cell line.
2003-01-14
Analysis of selected withanolides in plant extract by capillary electrochromatography and microemulsion electrokinetic chromatography.
2003-01
LC-MS/MS determination of a farnesyl transferase inhibitor in human plasma and urine.
2002-11-07
Determination of undecylenic and sorbic acids in cosmetic preparations by high performance liquid chromatography with electrochemical detection.
2002-11-07
Development and substantiation of a liquid chromatographic method for monitoring organic reactions involved in synthesis of 4-methoxyphenylacetic acid.
2002-10-04
A modified HPLC method for the determination of ochratoxin A by fluorescence detection.
2002-10
Interaction of cytochrome P450 3A inhibitors with P-glycoprotein.
2002-10
High-performance liquid chromatographic, capillary electrophoretic and capillary electrophoretic-electrospray ionisation mass spectrometric analysis of selected alkaloid groups.
2002-08-16
Augmentation of immune cell activity against tumor cells by Rauwolfia radix.
2002-08
Determination of terbutaline sulfate and its degradation products in pharmaceutical formulations using LC.
2002-07-31
Validated HPLC method for determination of sennosides A and B in senna tablets.
2002-07-31
Development and optimization of a reversed-phase high-performance liquid chromatographic method for the determination of piperacillin and tazobactam in tazocin injectable powder.
2002-07-31
[Application of fingerprint chromatogram in quality control of Shen-Mai injection].
2002-07
Determination of L-sesamin and L-asarinin in Zanthoxylum(Roxb.) DC. by high performance liquid chromatography.
2002-07
Increase of free cysteine and citric acid in plant cells exposed to cobalt ions.
2002-07
Determination of ethylenediamine tetraacetic acid in injection forms by ion-pair chromatography.
2002-06-15
Rapid high-performance liquid chromatographic assay of dorzolamide in rabbit aqueous humor.
2002-06
Validation of a simple liquid chromatographic method for determination and quantitation of residual ivermectin and doramectin in pig liver.
2002-05-07
Nitecapone and selegiline as effective adjuncts to L-DOPA in reserpine-induced catatonia in mice.
2002-05-01
[The effect of shourong compound formula on levels of dopamine and its metabolites in brain of Parkinson's disease mice induced by reserpine].
2002-05
[Determination of aspirin and free salicylic acid in lysinipirine injection by high performance liquid chromatography].
2002-05
Behavioral effects of MK-801 on reserpine-treated mice.
2002-04
Heterologous expression of a Rauvolfia cDNA encoding strictosidine glucosidase, a biosynthetic key to over 2000 monoterpenoid indole alkaloids.
2002-04
Simultaneous determination of N-oxides and free bases of pyrrolizidine alkaloids by cation-exchange solid-phase extraction and ion-pair high-performance liquid chromatography.
2002-03-08
[Determination of ofloxacin in human fallopian tube, uterus and serum by high performance liquid chromatography].
2002-02
Temperature effect on peak width and column efficiency in subcritical water chromatography.
2002-02
Studies on the cardiotoxicity of noradrenaline in isolated rabbit hearts.
2002
Identification of mammary carcinogens in rodent bioassays.
2002
[Determination of acyclovir in mouse plasma and tissues by reversed-phase high performance liquid chromatography].
2001-11
[Characterization and recognition key components in Astragalus membranaceus].
2001-07
[Determination of intestinal trefoil factor in burned rats by reversed-phase high performance liquid chromatography].
2001-07
[Determination of bifonazole in cream by high performance liquid chromatography].
2001-05
[Study of diphacinone in biological samples by high performance liquid chromatography/diode array detector].
2001-05
[Recognition and quantitative contrast characteristic components for root of Chinese angelica].
2001-03
[Behavior pharmacology of maprotiline, a new antidepressant].
1975-11
Effects of aminergic drugs and glutamic acid on audiogenic seizures induced by early exposure to ethanol.
1975-03
Patents

Sample Use Guides

Hypertension: In the average patient not receiving other antihypertensive agents, the usual initial dosage is 0.5 mg daily for 1 or 2 weeks. For maintenance, reduce to 0.1-0.25 mg daily. Psychiatric Disorders: the usual initial dosage is 0.5 mg daily, but may range from 0.1 mg to 1.0 mg. Adjust dosage upward or downward according to the patient's response.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:08:01 GMT 2025
Edited
by admin
on Mon Mar 31 23:08:01 GMT 2025
Record UNII
D632O8555Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RESERPINE ASCORBATE
Common Name English
L-ASCORBIC ACID, COMPD. WITH METHYL 18.BETA.-HYDROXY-11,17.ALPHA.-DIMETHOXY-3.BETA.,20.ALPHA.-YOHIMBAN-16.BETA.-CARBOXYLATE 3,4,5-TRIMETHOXYBENZOATE (ESTER)
Preferred Name English
3.BETA.,20.ALPHA.-YOHIMBAN-16.BETA.-CARBOXYLIC ACID, 18.BETA.-HYDROXY-11,17.ALPHA.-DIMETHOXY- METHYL ESTER 3,4,5-TRIMETHOXYBENZOATE (ESTER), L-ASCORBATE
Systematic Name English
YOHIMBAN-16-CARBOXYLIC ACID, 11,17-DIMETHOXY-18-((3,4,5-TRIMETHOXYBENZOYL)OXY)-, METHYL ESTER, (3.BETA.,16.BETA.,17.ALPHA.,18.BETA.,20.ALPHA.)-, MONO-L-ASCORBATE
Systematic Name English
RESERPINE, ASCORBATE
Common Name English
Code System Code Type Description
PUBCHEM
92135773
Created by admin on Mon Mar 31 23:08:01 GMT 2025 , Edited by admin on Mon Mar 31 23:08:01 GMT 2025
PRIMARY
CAS
20235-11-4
Created by admin on Mon Mar 31 23:08:01 GMT 2025 , Edited by admin on Mon Mar 31 23:08:01 GMT 2025
NON-SPECIFIC STOICHIOMETRY
FDA UNII
D632O8555Z
Created by admin on Mon Mar 31 23:08:01 GMT 2025 , Edited by admin on Mon Mar 31 23:08:01 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY