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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H40N2O9
Molecular Weight 608.6787
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RESERPINE

SMILES

CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C(NC5=C4C=CC(OC)=C5)[C@H]3C[C@@H]2[C@@H]1C(=O)OC)OC(=O)C6=CC(OC)=C(OC)C(OC)=C6

InChI

InChIKey=QEVHRUUCFGRFIF-MDEJGZGSSA-N
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

HIDE SMILES / InChI

Description

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.

CNS Activity

Originator

Approval Year

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RESERPINE
Palliative
RESERPINE

Cmax

ValueDoseCo-administeredAnalytePopulation
1.1 ng/mL
0.5 mg single, oral
RESERPINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
200 h
0.5 mg single, oral
RESERPINE plasma
Homo sapiens
4.5 h
0.25 mg single, oral
RESERPINE unknown
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
0.5 mg single, oral
RESERPINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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