Reserpine

Reserpine

Clinical data
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a601107
License data	US FDA: Reserpine
Pregnancy category	C
Routes of administration	Oral
ATC code	C02AA02 (WHO)
Legal status
Legal status	Rx-only (banned/discontinued in some countries)
Pharmacokinetic data
Bioavailability	50%
Metabolism	gut/liver
Biological half-life	phase 1 = 4.5h, phase 2 = 271h, average = 33h
Excretion	62% feces / 8% urine
Identifiers
IUPAC name methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
CAS Number	50-55-5 Y
PubChem CID	5770
IUPHAR/BPS	4823
DrugBank	DB00206 Y
ChemSpider	5566 Y
UNII	8B1QWR724A
KEGG	D00197 Y
ChEBI	CHEBI:28487 Y
ChEMBL	CHEMBL772 Y
ECHA InfoCard	100.000.044
Chemical and physical data
Formula	C33H40N2O9
Molar mass	608.68 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(OC)[C@H]6[C@H]4C[C@@H]3c2nc1cc(OC)ccc1c2CCN3C[C@H]4C[C@@H](OC(=O)c5cc(OC)c(OC)c(OC)c5)[C@@H]6OC
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 Y Key:QEVHRUUCFGRFIF-MDEJGZGSSA-N Y

Reserpine (also known by trade names Raudixin, Serpalan, Serpasil) 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. The antihypertensive actions of reserpine are a result of its ability to deplete catecholamines (among other monoamine neurotransmitters) from peripheral sympathetic nerve endings. These substances are normally involved in controlling heart rate, force of cardiac contraction and peripheral vascular resistance.

Reserpine-mediated depletion of monoamine neurotransmitters in the synapses is often cited as evidence to the theory that depletion of the monoamine neurotransmitters causes subsequent depression in humans (c.f. monoamine hypothesis). However, this claim is not without controversy. The reserpine-induced depression is considered by some researchers to be a myth, while others claim that teas made out of the plant roots containing reserpine have a calming, sedative action that can actually be considered antidepressant. Notably, reserpine was the first compound shown to be an effective antidepressant in a randomized placebo-controlled trial.

Moreover, reserpine has a peripheral action in many parts of the body, resulting in a preponderance of the effects of the cholinergic part of the autonomous nervous system on the GI tract, smooth muscles, blood vessels, etc.